A series of cyclopropane-1,1-diamide derivatives containing imidazo[1,2-a]pyridine were synthesized.The inhibitory effects of these compounds on FLT3-ITD kinase and their anti-proliferative activities against two acut...A series of cyclopropane-1,1-diamide derivatives containing imidazo[1,2-a]pyridine were synthesized.The inhibitory effects of these compounds on FLT3-ITD kinase and their anti-proliferative activities against two acute myeloid leukemia cell lines expressing FLT3-ITD were evaluated.With focused on the different substitutions of imidazo[1,2-a]pyridine,a preliminary exploration of the structure-activity relationship was conducted for 22 compounds.The results revealed that most compounds exhibited certain inhibitory effects on FLT3-ITD kinase with IC_(50) values below 0.5μmol·L^(-1).Among them,N-(4-fluorophenyl)-N-(4-(7-((2-morpholinoethyl)carbamoyl)imidazo[1,2-a]pyridine-3-carbonyl)phenyl)cyclopropane-1,1-dicarboxamide(12a)demonstrated the most potent FLT3-ITD kinase inhibitory activity and the strongest anti-proliferative effect on the MV4-11 and MOLM-13 cell lines expressing FLT3-ITD with IC50 values of 0.06 and 0.2μmol·L^(-1),respectively.Moreover,compound 12a did not exhibit anti-proliferative activity against cell lines without FLT3 mutations,such as THP-1,HCT-116,A549,HepG2,K562,and MCF-7,and it displayed non-cytotoxicity towards normal human renal tubular epithelial cells(HK-2),human liver progenitor cells(HepaRG),and HEK293(human embryonic kidney cells).Although 12a exhibits inferior inhibitory activity against FLT3-ITD kinase and anti-tumor cell proliferation compared to C abozantinib in this study,it can provide a reference for further research into FLT3-ITD inhibitors.展开更多
A direct Michael addition reaction between imidazo[1,2-a]pyridines andα,β-unsaturated ketones using acidic alumina as a C(sp3)—H acid catalyst has been developed.The abundant C(sp3)—H acid sites(Al^(3+))on the aci...A direct Michael addition reaction between imidazo[1,2-a]pyridines andα,β-unsaturated ketones using acidic alumina as a C(sp3)—H acid catalyst has been developed.The abundant C(sp3)—H acid sites(Al^(3+))on the acidic alumina surface effectively activate the carbonyl group ofα,β-unsaturated ketones,significantly enhancing the electrophilicity of theβ-carbon and thereby facilitating selective alkylation at the C3 position of imidazo[1,2-a]pyridines.This method demonstrates excellent functional group compatibility,mild reaction conditions,low reagent costs,and operational simplicity,providing a novel strategy for the efficient synthesis of alkylated imidazo[1,2-a]pyridine derivatives.展开更多
A series of new hexahydroimidazo[1,2-a]pyridine derivatives were synthesized via convenient and practical three-component reactions. Preliminary bioassays showed that majority of the target compounds exhibited moderat...A series of new hexahydroimidazo[1,2-a]pyridine derivatives were synthesized via convenient and practical three-component reactions. Preliminary bioassays showed that majority of the target compounds exhibited moderate to excellent insecticidal activity against cowpea aphids （Aphis craccivora）. Among them, compound 91 demonstrated significant activity with LCso value of 0.00918 mmol/L which was about 3.8-fold higher than that of imidacloprid （IMI）. Furthermore, the study of stereostructure-activity relationship of four isomers of 9k indicated that configuration played a key role in insecticidal activity of these compounds.展开更多
A cyclometalated greenish-yellow emitter 2,3-diphenylimidazo[1,2-a]pyridine iridium（Ill） complex is successfully synthesized and used to fabricate phosphorescent organic light-emitting diodes. The optimized device e...A cyclometalated greenish-yellow emitter 2,3-diphenylimidazo[1,2-a]pyridine iridium（Ill） complex is successfully synthesized and used to fabricate phosphorescent organic light-emitting diodes. The optimized device exhibits a greenish-yellow emission with the peak at 523nm and a strong shoulder at 557nm, corresponding to Commission Internationale de l＇Eclairage coordinates of （0.38, 0.68）. The full width at half maximum of the device is 93 nm, which is broader than the fac-tris（2-phenylpyridine）iridium [Ir（ppy）3] based reference device of 78 nm. Meanwhile, a maximum current efficiency of 62.6 cd/A （47.51m/W） is obtained. This result is higher than a maximum current efficiency of 54.8 cd/A （431m/W） of the Ir（ppy）a based device. The results indicate that this new iridium complex may have potential applications in fabricating high color rendering index white organic light emitting diodes.展开更多
Agricultural chemicals with multifunctional applications in crop protection have attracted increasing attention.Herein,two new series of thiazole and imidazo[1,2-a]pyridine derivatives containing a hydrazone substruct...Agricultural chemicals with multifunctional applications in crop protection have attracted increasing attention.Herein,two new series of thiazole and imidazo[1,2-a]pyridine derivatives containing a hydrazone substructure were designed and synthesized via a concise synthesis route.Bioassay results showed that most of the thiazole derivatives exhibited broad-spectrum fungistatic activities,which were exemplified by compounds 1c,1e,1g,1h and 1j.In particular,compound 1e displayed excellent in vitro inhibitory effects with the EC50 values of 5.00,18.24,6.94,and 3.03μg/mL against the fungi Botrytis cinerea,Cytospora sp,Fusarium graminearum,and Fusarium solani,respectively.Detached fruit experiments against tomato gray mold(caused by B.cinerea)in vivo revealed that the control efficiency of compound 1e at 10,20 and 40μg/mL for 5 days was 35.05%,54.14%and 81.83%,respectively,which was comparable and even superior to that of the fungicide carbendazim.Additionally,the title compounds also showed remarkable larvicidal activity against M.separata and some compounds exhibited good aphicidal activity.In a word,the bioassay indicated that a certain number of title compounds had multiple biological activities.Given their excellent antifungal and larvicidal characteristics,these interesting derivatives based on the title compounds could be served as new scaffolds for the development of pesticide with multifunctional applications.展开更多
A series of substituted 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamides derivatives 5a-5m were synthesized through multi-step reactions. To achieve the synthesis of the desired compounds monobromo and dibromo substi...A series of substituted 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamides derivatives 5a-5m were synthesized through multi-step reactions. To achieve the synthesis of the desired compounds monobromo and dibromo substituted 2-amino-γ-picoline was reacted with ethyl 2-chloroacetoacetate. The crude ethyl ester subjected to hydrolysis in presence of lithium hydroxide to get 2a and 2b, with imidazo[1,2-a]pyri- dine-3-carboxylic acid to get 3a-3b, on treatment with substituted amines 4a-4g to get desired product 5a-5m in presence of EDCI and HOBt. The substituted imidazo[1,2-a]pyridine-3-carboxamides are characterized by FTIR, 1H-NMR, 13C-NMR and mass spectra. These newly synthesized compounds were tested in vitro for their antimycobacterial activity. The preliminary results of antituberculosis study showed that most of the synthesized compounds 5a-5m demonstrated moderate to good antituberculosis activity. Among the tested compounds 5b, 5d and 5e were found to be the most active with minimum inhibitory concentration (MIC) of 12.5 μg/mL against Mycobacterium tuberculosis (H37 RV strain) ATCC No-27294.展开更多
Seven 2,6-disubstituted N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamide series containing various amine moieties were designed and synthesized as new anti-TB agents.Many of them show excellent in vitro activit...Seven 2,6-disubstituted N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamide series containing various amine moieties were designed and synthesized as new anti-TB agents.Many of them show excellent in vitro activity against both drug-sensitive MTB strain H37Rv and two MDR-MTB clinical isolates(MIC:<0.002-0.030 μg/mL).Compounds 2f,5e and 5g display acceptable safety and pharmacokinetic profiles,opening a new direction for further development.展开更多
Abundant efforts have been devoted to improving the efficiency of organic light-emitting diodes(OLEDs),however,approaches to control the device efficiency roll-off are still extremely limited,especially in nondoped bl...Abundant efforts have been devoted to improving the efficiency of organic light-emitting diodes(OLEDs),however,approaches to control the device efficiency roll-off are still extremely limited,especially in nondoped blue OLEDs.In this work,three blue emitters(TAT,TAMT and TAMT-CN)with"hot exciton"properties are designed and synthesized based on[1,2,4]triazolo[1,5-a]pyridine(TP)as a regulating unit as well as anthracene-triphenylamine(An-TPA)as the chromophore.By adjusting the linkage mode and modifying the TP unit,the excited state properties,carrier transfer abilities,horizontal orientation,and device efficiency roll-off were precisely controlled.Among these materials,emitters that directly connect the fused TP unit exhibit balanced charge-transporting ability,higher photoluminescent quantum yield and improved horizontal orientation,resulting in better electroluminescence(EL)performance in non-doped blue OLEDs.As a result,non-doped blue OLEDs exhibit excellent performance with external quantum efficiencies of over 6%,brightness of over 30,000 cd/m2and EL peaks of around 476 nm.More importantly,the device based on TAMT-CN exhibits an ultra-low efficiency roll-off of 2.97%at a high brightness of10,000 cd/m2.The accessible molecular unit and feasible design strategy in this work are of great significance for designing highly efficient and ultra-low efficiency roll-off non-doped blue OLEDs.展开更多
A transition-metal-and oxidant-free amination/cyclization reaction to access 1,2,4-triazolo[1,5-a]pyridines was realized in water by using amino diphenylphosphinate as amino source.A broad array of readily accessible ...A transition-metal-and oxidant-free amination/cyclization reaction to access 1,2,4-triazolo[1,5-a]pyridines was realized in water by using amino diphenylphosphinate as amino source.A broad array of readily accessible N-(pyridyl)amides could be converted into the products featuring a diverse set of functional groups.The sustainable methodology was successfully applied to the late-stage functionalization of natural products and drugs.展开更多
A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported,charactering mild and environmentally benign conditi...A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported,charactering mild and environmentally benign conditions,as well as great functional group tolerance.Micelles with negatively charged polar surface and hydrophobic core formed from sodium dodecyl sulfate serve as an ideal medium for visible-light mediated radical reaction of cationic pyridine salt and imidazo[1,2-a]pyridine in aqueous phase.The electrostatic interaction between positively charged N-aminopyridinium and negatively charged surface of micelles is of great significance in this method.展开更多
An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[ 1,2-a]pyridines from easily available starting materials： Aromatic ketones, α/βunsaturated ketones,β-keto esters and 2- aminopyri...An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[ 1,2-a]pyridines from easily available starting materials： Aromatic ketones, α/βunsaturated ketones,β-keto esters and 2- aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined bv X-ray crystallographic analysis.展开更多
A visible-light-induced C-5 selective C-H borylation of imidazo[1,2-a]pyridines with NHC-BH3 via Minisci-type radical borylation re-action has been developed for the first time.The present sustainable protocol provide...A visible-light-induced C-5 selective C-H borylation of imidazo[1,2-a]pyridines with NHC-BH3 via Minisci-type radical borylation re-action has been developed for the first time.The present sustainable protocol provides a new family of regioselectively C5-borylated imidazopyridines that would otherwise be difficult to prepare.It is a supplement to site-selective borylation of azines(nitrogen-con-taining aromatic heterocycles)and the assembly of sp2 carbon-boron bond.展开更多
Imidazo[1,2-a]pyridines are present in numerous biologically active compounds as the core structural motif.Herein,we report an asymmetric interrupted Barton-Zard reaction of electron-deficient imidazo[1,2-a]pyridines ...Imidazo[1,2-a]pyridines are present in numerous biologically active compounds as the core structural motif.Herein,we report an asymmetric interrupted Barton-Zard reaction of electron-deficient imidazo[1,2-a]pyridines withα-substituted isocyanoacetates.The reaction enables the dearomatization of 8-nitroimidazo[1,2-a]pyridines and hence offers straightforward access to an array of optically active highly functionalized imidazo[1,2-a]pyridine derivatives that possess three contiguous stereogenic centers in good yields(up to 98%)with high stereoselectivities(>19:1 dr,>99%ee).It is worth noting that the catalytic system consisting of a chiral squaramide and silver oxide displays remarkable reactivity and stereoselectivity,and a gram-scale reaction is compatible with the catalyst loading of 0.5 mol%.In addition,the synthetic potential of this method was showcased by versatile transformations of the product.展开更多
Imidazo[1,2-a]pyridines have been successfully synthesized in moderate to good yields via a tandem three- component reaction of ethyl 2-（3-oxo-3-arylpropanethioamido）acetates with aromatic aldehydes and malononitril...Imidazo[1,2-a]pyridines have been successfully synthesized in moderate to good yields via a tandem three- component reaction of ethyl 2-（3-oxo-3-arylpropanethioamido）acetates with aromatic aldehydes and malononitrile by means of microwave irradiation using DABCO as the catalyst. The advantages of this method including high chemo- and regioselectivity make this new strategy highly attractive.展开更多
The light-driven CO_(2)reduction reaction(CO_(2)RR)to CO is a very effective way to address global warming.To avoid competition with water photolysis,metal-free gas-solid CO_(2)RR catalysts should be investigated.Cova...The light-driven CO_(2)reduction reaction(CO_(2)RR)to CO is a very effective way to address global warming.To avoid competition with water photolysis,metal-free gas-solid CO_(2)RR catalysts should be investigated.Covalent organic frameworks(COFs)offer a promising approach for CO_(2)transformation but lack high efficiency and selectivity in the absence of metals.Here,we have incorporated a pyridine nitrogen component into the imine-COF conjugated structure(Tp Pym).This innovative system has set a record of producing a CO yield of 1565μmol g^(-1)within 6 h.The soft X-ray absorption fine structure measurement proves that Tp Pym has both better conjugation and electron cloud enrichment.The electronic structure distribution delays the charge-carrier recombination,as evidenced by femtosecond transient absorption spectroscopy.The energy band diagram and theoretical calculation show that the conduction-band potential of Tp Pym is lower and the reduction reaction of CO_(2)to CO is more likely to occur.展开更多
Imidazo[1,2-a]pyridines are unique nitrogen-containing organic compounds with wide applications in pharma-ceuticals,natural products,material science and organometallics.Due to their significant biological and synthet...Imidazo[1,2-a]pyridines are unique nitrogen-containing organic compounds with wide applications in pharma-ceuticals,natural products,material science and organometallics.Due to their significant biological and synthetic value,the construction of imidazo[1,2-a]pyridine scaffolds has been a highly intriguing research topic,and substantial progress had been made in the past decades.In this review,we aim to summarize the current advances in direct C–H functionalization of imidazo[1,2-a]pyridines under transition-metal-free conditions.For the selected examples,we focused on the design and catalytic cycle mechanism,as well as on representative outcomes and applications.展开更多
Objectives The discovery of novel molecular targets to enhance the osteogenesis of human bone marrow-derived mesenchymal stem cells(H-BMSCs)represents a promising strategy for preventing and treating osteoporosis.Thus...Objectives The discovery of novel molecular targets to enhance the osteogenesis of human bone marrow-derived mesenchymal stem cells(H-BMSCs)represents a promising strategy for preventing and treating osteoporosis.Thus,the primary objective of this study is to elucidate the mechanisms by which long non-coding RNA FOXD2-AS1(lncRNA FOXD2-AS1)regulates early osteogenic differentiation in H-BMSCs,thereby identifying potential therapeutic targets.Methods Lentivirus-mediated vectors were constructed to either overexpress or silence FOXD2-AS1 in H-BMSCs.The effects of FOXD2-AS1 on osteogenesis were subsequently assessed by analyzing osteogenic marker expression and alkaline phosphatase(ALP)staining.To clarify the role of the Janus kinase 2/signal transducer and activator of transcription 3(JAK2/STAT3)pathway in this process,AG490 inhibitor(a JAK2/STAT3 pathway inhibitor)and knockdown of STAT3 were used to investigate the mechanisms of FOXD2-AS1.Results FOXD2-AS1 overexpression increased ALP activity and osteogenic marker expression,while its knockdown had the opposite effects.From a mechanistic perspective,FOXD2-AS1 overexpression promoted JAK2 and STAT3 phosphorylation,whereas its suppression attenuated their activation.Also,the osteogenic increase induced by FOXD2-AS1 overexpression was reversed by AG490 treatment or STAT3 silencing,indicating that the pathway plays a role in this process.Conclusion FOXD2-AS1 was identified as a novel genetic switch driving osteogenic commitment via JAK2/STAT3 activation,revealing a new regulatory mechanism and a potential therapeutic target for osteoporosis.展开更多
The title compound 8-chloro-3-（（4-chlorobenzyl）thio）-[1,2,4]triazolo[4,3-a]pyridine was prepared from 1-chloro-4-（chloromethyl）benzene and 8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3（2H）-thione in the presence o...The title compound 8-chloro-3-（（4-chlorobenzyl）thio）-[1,2,4]triazolo[4,3-a]pyridine was prepared from 1-chloro-4-（chloromethyl）benzene and 8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3（2H）-thione in the presence of Na OH, and its structure was determined by X-ray diffraction analysis. The crystal is of triclinic system, space group P1 with a = 6.8264（6）, b = 7.5890（4）, c = 13.0960（7） A, α = 93.447（4）, β = 98.772（6）, γ = 92.615（6）o, V = 668.26（8） A3, Z = 2, the final R = 0.035 and wR = 0.09 for 2259 observed reflections with I 〉 2σ（I）. The preliminary biological test showed that the title compound has activities against Stemphylium lycopersici（Enjoji） Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea with inhibitory to be 51.19%, 62.02% and 15.56%, respectively.展开更多
Reaction of 3-（pyridin-2-yl）-imidazo[1,5-a]pyridine （HPIP）, CuCi2·2H20 and picolinaldehyde in the mixture of CHaCOOH and EtOH under solvothermal conditions gave complexes [LCuCI][CuECI3] （1） and [HLCuC1]E[C...Reaction of 3-（pyridin-2-yl）-imidazo[1,5-a]pyridine （HPIP）, CuCi2·2H20 and picolinaldehyde in the mixture of CHaCOOH and EtOH under solvothermal conditions gave complexes [LCuCI][CuECI3] （1） and [HLCuC1]E[CuCI2]2[CuCI3].2H20 （2） （L = 1,1＇-（pyridin-2- ylmethylene）bis[3-（pyridin-2-yl）imidazo[1,5-a]pyridine]） simultaneously. The ligand L was generated via in situ metal-ligand reaction between HPIP and picolinaldehyde. When CuCI2·2H20 was replaced by CuC1, the 2：1：1（HPIP：picolinaldehyde：CuCI） reaction afforded complex [CuaL2CI2][CuCI2]·2H20 （3） and the analogous 2：1：3 reaction generated compound [CuaL2][CuCI2]3 （4）. Complexes 1 and 2 are Cun/CuI mixed-valence compounds. Complexes 1-4 display four various structures. It is found that the formation of the L ligand is controlled by CH3COOH. This work reveals that the structures of complexes 1-4 could be rationally tuned via the inclusion of CH3COOH in the reaction systems, the proper selection of different starting materials and the dexterous adjustment of the ratio of the starting materials.展开更多
文摘A series of cyclopropane-1,1-diamide derivatives containing imidazo[1,2-a]pyridine were synthesized.The inhibitory effects of these compounds on FLT3-ITD kinase and their anti-proliferative activities against two acute myeloid leukemia cell lines expressing FLT3-ITD were evaluated.With focused on the different substitutions of imidazo[1,2-a]pyridine,a preliminary exploration of the structure-activity relationship was conducted for 22 compounds.The results revealed that most compounds exhibited certain inhibitory effects on FLT3-ITD kinase with IC_(50) values below 0.5μmol·L^(-1).Among them,N-(4-fluorophenyl)-N-(4-(7-((2-morpholinoethyl)carbamoyl)imidazo[1,2-a]pyridine-3-carbonyl)phenyl)cyclopropane-1,1-dicarboxamide(12a)demonstrated the most potent FLT3-ITD kinase inhibitory activity and the strongest anti-proliferative effect on the MV4-11 and MOLM-13 cell lines expressing FLT3-ITD with IC50 values of 0.06 and 0.2μmol·L^(-1),respectively.Moreover,compound 12a did not exhibit anti-proliferative activity against cell lines without FLT3 mutations,such as THP-1,HCT-116,A549,HepG2,K562,and MCF-7,and it displayed non-cytotoxicity towards normal human renal tubular epithelial cells(HK-2),human liver progenitor cells(HepaRG),and HEK293(human embryonic kidney cells).Although 12a exhibits inferior inhibitory activity against FLT3-ITD kinase and anti-tumor cell proliferation compared to C abozantinib in this study,it can provide a reference for further research into FLT3-ITD inhibitors.
文摘A direct Michael addition reaction between imidazo[1,2-a]pyridines andα,β-unsaturated ketones using acidic alumina as a C(sp3)—H acid catalyst has been developed.The abundant C(sp3)—H acid sites(Al^(3+))on the acidic alumina surface effectively activate the carbonyl group ofα,β-unsaturated ketones,significantly enhancing the electrophilicity of theβ-carbon and thereby facilitating selective alkylation at the C3 position of imidazo[1,2-a]pyridines.This method demonstrates excellent functional group compatibility,mild reaction conditions,low reagent costs,and operational simplicity,providing a novel strategy for the efficient synthesis of alkylated imidazo[1,2-a]pyridine derivatives.
基金supported by National Key Technology R&D Program of China(No.2011BAE06B01)
文摘A series of new hexahydroimidazo[1,2-a]pyridine derivatives were synthesized via convenient and practical three-component reactions. Preliminary bioassays showed that majority of the target compounds exhibited moderate to excellent insecticidal activity against cowpea aphids （Aphis craccivora）. Among them, compound 91 demonstrated significant activity with LCso value of 0.00918 mmol/L which was about 3.8-fold higher than that of imidacloprid （IMI）. Furthermore, the study of stereostructure-activity relationship of four isomers of 9k indicated that configuration played a key role in insecticidal activity of these compounds.
文摘A cyclometalated greenish-yellow emitter 2,3-diphenylimidazo[1,2-a]pyridine iridium（Ill） complex is successfully synthesized and used to fabricate phosphorescent organic light-emitting diodes. The optimized device exhibits a greenish-yellow emission with the peak at 523nm and a strong shoulder at 557nm, corresponding to Commission Internationale de l＇Eclairage coordinates of （0.38, 0.68）. The full width at half maximum of the device is 93 nm, which is broader than the fac-tris（2-phenylpyridine）iridium [Ir（ppy）3] based reference device of 78 nm. Meanwhile, a maximum current efficiency of 62.6 cd/A （47.51m/W） is obtained. This result is higher than a maximum current efficiency of 54.8 cd/A （431m/W） of the Ir（ppy）a based device. The results indicate that this new iridium complex may have potential applications in fabricating high color rendering index white organic light emitting diodes.
基金supported by the National Natural Science Foundation of China(31972303)the Natural Science Basic Research Program of Shaanxi Province(Program No.2023-JC-YB-144,2023-JC-YB-719).
文摘Agricultural chemicals with multifunctional applications in crop protection have attracted increasing attention.Herein,two new series of thiazole and imidazo[1,2-a]pyridine derivatives containing a hydrazone substructure were designed and synthesized via a concise synthesis route.Bioassay results showed that most of the thiazole derivatives exhibited broad-spectrum fungistatic activities,which were exemplified by compounds 1c,1e,1g,1h and 1j.In particular,compound 1e displayed excellent in vitro inhibitory effects with the EC50 values of 5.00,18.24,6.94,and 3.03μg/mL against the fungi Botrytis cinerea,Cytospora sp,Fusarium graminearum,and Fusarium solani,respectively.Detached fruit experiments against tomato gray mold(caused by B.cinerea)in vivo revealed that the control efficiency of compound 1e at 10,20 and 40μg/mL for 5 days was 35.05%,54.14%and 81.83%,respectively,which was comparable and even superior to that of the fungicide carbendazim.Additionally,the title compounds also showed remarkable larvicidal activity against M.separata and some compounds exhibited good aphicidal activity.In a word,the bioassay indicated that a certain number of title compounds had multiple biological activities.Given their excellent antifungal and larvicidal characteristics,these interesting derivatives based on the title compounds could be served as new scaffolds for the development of pesticide with multifunctional applications.
文摘A series of substituted 2,7-dimethylimidazo[1,2-a]pyridine-3-carboxamides derivatives 5a-5m were synthesized through multi-step reactions. To achieve the synthesis of the desired compounds monobromo and dibromo substituted 2-amino-γ-picoline was reacted with ethyl 2-chloroacetoacetate. The crude ethyl ester subjected to hydrolysis in presence of lithium hydroxide to get 2a and 2b, with imidazo[1,2-a]pyri- dine-3-carboxylic acid to get 3a-3b, on treatment with substituted amines 4a-4g to get desired product 5a-5m in presence of EDCI and HOBt. The substituted imidazo[1,2-a]pyridine-3-carboxamides are characterized by FTIR, 1H-NMR, 13C-NMR and mass spectra. These newly synthesized compounds were tested in vitro for their antimycobacterial activity. The preliminary results of antituberculosis study showed that most of the synthesized compounds 5a-5m demonstrated moderate to good antituberculosis activity. Among the tested compounds 5b, 5d and 5e were found to be the most active with minimum inhibitory concentration (MIC) of 12.5 μg/mL against Mycobacterium tuberculosis (H37 RV strain) ATCC No-27294.
基金supported by the CAMS Innovation Fund for Medical Science(No.CAMS-2017-I2M-1-011)National Mega-project for Innovative Drugs(Nos.2015ZX09102007-008,2018ZX09721001004-007,2018ZX09711001-007-002)the National Natural Science Foundation of China(No.81872753)。
文摘Seven 2,6-disubstituted N-(2-phenoxy)ethyl imidazo[1,2-a]pyridine-3-carboxamide series containing various amine moieties were designed and synthesized as new anti-TB agents.Many of them show excellent in vitro activity against both drug-sensitive MTB strain H37Rv and two MDR-MTB clinical isolates(MIC:<0.002-0.030 μg/mL).Compounds 2f,5e and 5g display acceptable safety and pharmacokinetic profiles,opening a new direction for further development.
基金the financial support from the National Natural Science Foundation of China(Nos.52273187 and 51973107)the Guangdong Province Universities and Colleges Pearl River Scholar Funded Scheme 2019(No.GDUPS2019)。
文摘Abundant efforts have been devoted to improving the efficiency of organic light-emitting diodes(OLEDs),however,approaches to control the device efficiency roll-off are still extremely limited,especially in nondoped blue OLEDs.In this work,three blue emitters(TAT,TAMT and TAMT-CN)with"hot exciton"properties are designed and synthesized based on[1,2,4]triazolo[1,5-a]pyridine(TP)as a regulating unit as well as anthracene-triphenylamine(An-TPA)as the chromophore.By adjusting the linkage mode and modifying the TP unit,the excited state properties,carrier transfer abilities,horizontal orientation,and device efficiency roll-off were precisely controlled.Among these materials,emitters that directly connect the fused TP unit exhibit balanced charge-transporting ability,higher photoluminescent quantum yield and improved horizontal orientation,resulting in better electroluminescence(EL)performance in non-doped blue OLEDs.As a result,non-doped blue OLEDs exhibit excellent performance with external quantum efficiencies of over 6%,brightness of over 30,000 cd/m2and EL peaks of around 476 nm.More importantly,the device based on TAMT-CN exhibits an ultra-low efficiency roll-off of 2.97%at a high brightness of10,000 cd/m2.The accessible molecular unit and feasible design strategy in this work are of great significance for designing highly efficient and ultra-low efficiency roll-off non-doped blue OLEDs.
基金financial support from the National Natural Science Foundation of China(No.82003585)the Program for Science&Technology Innovation Talents in Universities of Henan Province(No.24HASTIT069)+5 种基金the Technical Innovation Team of Henan Normal University(No.2022TD03)the Special Project for Fundamental Research in University of Henan Province(No.23ZX009)the Henan Science and Technology Program(No.232102310364)the Key Project of Henan Educational Committee(No.22A150041)Excellent Youth Foundation of Henan Scientific Committee(No.222300420012)the Young Core Instructor Training Program of Xinyang Agriculture and Forestry University(2023)。
文摘A transition-metal-and oxidant-free amination/cyclization reaction to access 1,2,4-triazolo[1,5-a]pyridines was realized in water by using amino diphenylphosphinate as amino source.A broad array of readily accessible N-(pyridyl)amides could be converted into the products featuring a diverse set of functional groups.The sustainable methodology was successfully applied to the late-stage functionalization of natural products and drugs.
基金We thank the National Natural Science Foundation of China(Grant Nos.21901216 and 21871031)the Fund of Science and Technology Agency of Chengdu(2019-YF09-00049-SN)+1 种基金the Open Project Program of Irradiation Preservation Technology Key Laboratory of Sichuan Province,Sichuan Institute of Atomic Energy(No.FZBC2020002)the Sichuan Science and Technology Program(2020YFH0061,2020YJ0222,2021JDRC0018,2021YFS0092,2021YFSY0041,2021YFH0064).
文摘A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported,charactering mild and environmentally benign conditions,as well as great functional group tolerance.Micelles with negatively charged polar surface and hydrophobic core formed from sodium dodecyl sulfate serve as an ideal medium for visible-light mediated radical reaction of cationic pyridine salt and imidazo[1,2-a]pyridine in aqueous phase.The electrostatic interaction between positively charged N-aminopyridinium and negatively charged surface of micelles is of great significance in this method.
基金the National Natural Science Foundation of China (Nos. 21032001 and 21272085) for their generous financial supportthe excellent doctorial dissertation cultivation grant from Central China Normal University Wuhan, China (No. 2013YBYB63)
文摘An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[ 1,2-a]pyridines from easily available starting materials： Aromatic ketones, α/βunsaturated ketones,β-keto esters and 2- aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined bv X-ray crystallographic analysis.
基金This work was supported by the Innovation and Strong School Project of Guangdong Pharmaceutical University(2021ZDzX2028)the Scientific and Technological Innovation Leading Talent Project of Zhongshan City(LJ2021009)a Start-up Grant from Guangdong Pharmaceutical University(Grant Nos.51361303,51361304).
文摘A visible-light-induced C-5 selective C-H borylation of imidazo[1,2-a]pyridines with NHC-BH3 via Minisci-type radical borylation re-action has been developed for the first time.The present sustainable protocol provides a new family of regioselectively C5-borylated imidazopyridines that would otherwise be difficult to prepare.It is a supplement to site-selective borylation of azines(nitrogen-con-taining aromatic heterocycles)and the assembly of sp2 carbon-boron bond.
基金supported by the National Key R&D Program of China(2021YFA1500100)the National Natural Science Foundation of China(21821002,22031012,and 22171282)the Science and Technology Commission of Shanghai Municipality(19590750400 and 21520780100)。
文摘Imidazo[1,2-a]pyridines are present in numerous biologically active compounds as the core structural motif.Herein,we report an asymmetric interrupted Barton-Zard reaction of electron-deficient imidazo[1,2-a]pyridines withα-substituted isocyanoacetates.The reaction enables the dearomatization of 8-nitroimidazo[1,2-a]pyridines and hence offers straightforward access to an array of optically active highly functionalized imidazo[1,2-a]pyridine derivatives that possess three contiguous stereogenic centers in good yields(up to 98%)with high stereoselectivities(>19:1 dr,>99%ee).It is worth noting that the catalytic system consisting of a chiral squaramide and silver oxide displays remarkable reactivity and stereoselectivity,and a gram-scale reaction is compatible with the catalyst loading of 0.5 mol%.In addition,the synthetic potential of this method was showcased by versatile transformations of the product.
文摘Imidazo[1,2-a]pyridines have been successfully synthesized in moderate to good yields via a tandem three- component reaction of ethyl 2-（3-oxo-3-arylpropanethioamido）acetates with aromatic aldehydes and malononitrile by means of microwave irradiation using DABCO as the catalyst. The advantages of this method including high chemo- and regioselectivity make this new strategy highly attractive.
基金supported by the National Natural Science Foundation of China(Nos.22375031,22202037,22472023)the Fundamental Research Funds for the Central Universities(Nos.2412023YQ001,2412023QD019,2412024QD014)+1 种基金supported by grants from the seventh batch of Jilin Province Youth Science and Technology Talent Lifting Project(No.QT202305)Science and Technology Development Plan Project of Jilin Province,China(No.20240101192JC)。
文摘The light-driven CO_(2)reduction reaction(CO_(2)RR)to CO is a very effective way to address global warming.To avoid competition with water photolysis,metal-free gas-solid CO_(2)RR catalysts should be investigated.Covalent organic frameworks(COFs)offer a promising approach for CO_(2)transformation but lack high efficiency and selectivity in the absence of metals.Here,we have incorporated a pyridine nitrogen component into the imine-COF conjugated structure(Tp Pym).This innovative system has set a record of producing a CO yield of 1565μmol g^(-1)within 6 h.The soft X-ray absorption fine structure measurement proves that Tp Pym has both better conjugation and electron cloud enrichment.The electronic structure distribution delays the charge-carrier recombination,as evidenced by femtosecond transient absorption spectroscopy.The energy band diagram and theoretical calculation show that the conduction-band potential of Tp Pym is lower and the reduction reaction of CO_(2)to CO is more likely to occur.
基金support from the National Natural Science Foundation of China(Grant Nos.22101267)Natural Science Foundation of Henan Province(222300420084)application research plan of key scientific research projects in colleges and universities of Henan Province(22A150056).
文摘Imidazo[1,2-a]pyridines are unique nitrogen-containing organic compounds with wide applications in pharma-ceuticals,natural products,material science and organometallics.Due to their significant biological and synthetic value,the construction of imidazo[1,2-a]pyridine scaffolds has been a highly intriguing research topic,and substantial progress had been made in the past decades.In this review,we aim to summarize the current advances in direct C–H functionalization of imidazo[1,2-a]pyridines under transition-metal-free conditions.For the selected examples,we focused on the design and catalytic cycle mechanism,as well as on representative outcomes and applications.
基金supported by the Natural Science Foundation of Hubei Province of China(Grant No.2023AFB671)the National Natural Science Foundation of China(Grant Nos.82360177 and 82560182)+1 种基金the Key Project of Jiangxi Provincial Natural Science Foundation(Grant No.20224ACB206011)“Xuncheng Talents”Project in Jiujiang City,Jiangxi Province(Grant No.JJXC2023071).
文摘Objectives The discovery of novel molecular targets to enhance the osteogenesis of human bone marrow-derived mesenchymal stem cells(H-BMSCs)represents a promising strategy for preventing and treating osteoporosis.Thus,the primary objective of this study is to elucidate the mechanisms by which long non-coding RNA FOXD2-AS1(lncRNA FOXD2-AS1)regulates early osteogenic differentiation in H-BMSCs,thereby identifying potential therapeutic targets.Methods Lentivirus-mediated vectors were constructed to either overexpress or silence FOXD2-AS1 in H-BMSCs.The effects of FOXD2-AS1 on osteogenesis were subsequently assessed by analyzing osteogenic marker expression and alkaline phosphatase(ALP)staining.To clarify the role of the Janus kinase 2/signal transducer and activator of transcription 3(JAK2/STAT3)pathway in this process,AG490 inhibitor(a JAK2/STAT3 pathway inhibitor)and knockdown of STAT3 were used to investigate the mechanisms of FOXD2-AS1.Results FOXD2-AS1 overexpression increased ALP activity and osteogenic marker expression,while its knockdown had the opposite effects.From a mechanistic perspective,FOXD2-AS1 overexpression promoted JAK2 and STAT3 phosphorylation,whereas its suppression attenuated their activation.Also,the osteogenic increase induced by FOXD2-AS1 overexpression was reversed by AG490 treatment or STAT3 silencing,indicating that the pathway plays a role in this process.Conclusion FOXD2-AS1 was identified as a novel genetic switch driving osteogenic commitment via JAK2/STAT3 activation,revealing a new regulatory mechanism and a potential therapeutic target for osteoporosis.
基金funded by the National Natural Science Foundation of China(No.21002090)the Natural Science Foundation of Zhejiang Province(No.LY16C140007)the public program of Science and Technology of Zhejiang Province(2014C31127,2013C32SA700134)
文摘The title compound 8-chloro-3-（（4-chlorobenzyl）thio）-[1,2,4]triazolo[4,3-a]pyridine was prepared from 1-chloro-4-（chloromethyl）benzene and 8-chloro-[1,2,4]triazolo[4,3-a]pyridine-3（2H）-thione in the presence of Na OH, and its structure was determined by X-ray diffraction analysis. The crystal is of triclinic system, space group P1 with a = 6.8264（6）, b = 7.5890（4）, c = 13.0960（7） A, α = 93.447（4）, β = 98.772（6）, γ = 92.615（6）o, V = 668.26（8） A3, Z = 2, the final R = 0.035 and wR = 0.09 for 2259 observed reflections with I 〉 2σ（I）. The preliminary biological test showed that the title compound has activities against Stemphylium lycopersici（Enjoji） Yamamoto, Fusarium oxysporum. sp. cucumebrium, and Botrytis cinerea with inhibitory to be 51.19%, 62.02% and 15.56%, respectively.
基金Supported by NNSFC(21272167)the Priority Academic Program Development of Jiangsu Higher Education Institution,and KLSLRC(KLSLRC-KF-13-HX-1)
文摘Reaction of 3-（pyridin-2-yl）-imidazo[1,5-a]pyridine （HPIP）, CuCi2·2H20 and picolinaldehyde in the mixture of CHaCOOH and EtOH under solvothermal conditions gave complexes [LCuCI][CuECI3] （1） and [HLCuC1]E[CuCI2]2[CuCI3].2H20 （2） （L = 1,1＇-（pyridin-2- ylmethylene）bis[3-（pyridin-2-yl）imidazo[1,5-a]pyridine]） simultaneously. The ligand L was generated via in situ metal-ligand reaction between HPIP and picolinaldehyde. When CuCI2·2H20 was replaced by CuC1, the 2：1：1（HPIP：picolinaldehyde：CuCI） reaction afforded complex [CuaL2CI2][CuCI2]·2H20 （3） and the analogous 2：1：3 reaction generated compound [CuaL2][CuCI2]3 （4）. Complexes 1 and 2 are Cun/CuI mixed-valence compounds. Complexes 1-4 display four various structures. It is found that the formation of the L ligand is controlled by CH3COOH. This work reveals that the structures of complexes 1-4 could be rationally tuned via the inclusion of CH3COOH in the reaction systems, the proper selection of different starting materials and the dexterous adjustment of the ratio of the starting materials.
