Photocatalytic and photoinduced silyl radicals cascade cyclization procedures for the green and simple preparation of fused tetracyclic skeleton silylated indolo[2,1-a]isoquinoline-6(5H)-ones from 2-aryl-N-acryloyl in...Photocatalytic and photoinduced silyl radicals cascade cyclization procedures for the green and simple preparation of fused tetracyclic skeleton silylated indolo[2,1-a]isoquinoline-6(5H)-ones from 2-aryl-N-acryloyl indoles with hydrosilanes are developed.The photocatalytic reaction is carried out with 9,10-dicyanoanthracene(DCA)as an organophotocatalyst and 3-acetoxyquinuclidine as hydrogen atom transfer(HAT)catalyst at room temperature under metal-and oxidant-free conditions.The keys to the success of photoredox-catalytic conversion include(1)the reductive quenching of DCA^(*)[E_(1/2)(*P/P^(-))=+1.97 V vs.SCE in MeCN]by 3-acetoxyquinuclidine(E_(p)=+1.22 V vs.SCE in MeCN),and(2)the thermodynamic feasibility of hydrogen atom abstraction from hydridic Si-H bond by electrophilic N^(+·).Particularly,the simple photoinduced cascade cyclization using(TMS)3SiH with 2-aryl-N-acryloyl indoles was exploited via an electron-donor-acceptor(EDA)complex under visible light irradiation.展开更多
Four new isoquinoline alkaloids,hypecotumines A-D(1-4),were isolated and identified from the whole herbs of Hypecoum erectum L.Their structures were determined by a combination of HRESIMS,NMR,and X-ray diffraction ana...Four new isoquinoline alkaloids,hypecotumines A-D(1-4),were isolated and identified from the whole herbs of Hypecoum erectum L.Their structures were determined by a combination of HRESIMS,NMR,and X-ray diffraction analysis methods.Compounds 1-4 were characterized by a terminal double bond at C-9 and their plausible biosynthetic pathway was hypothesized.Since PCSK9 plays a key role in the development of cardiovascular disease(CVD),exploration of PCSK inhibitors from natural products are beneficial for drug discovery of CVD treatment.SPR and Western blot assays showed compound 4 had PCSK9 inhibition activity with KD value of 59.9μM and thus elevated the LDLR level.Further molecular docking studies demonstrated that 4 and PCSK9 could form stable interactions via key hydrogen bonds.展开更多
By using active principles of Chinese medicinal materials as lead compounds soquinoline derivatives have been designed and synthesized.Their chemical structures include bisbenzylisoquinoline,benzyl-isoquinoline and pr...By using active principles of Chinese medicinal materials as lead compounds soquinoline derivatives have been designed and synthesized.Their chemical structures include bisbenzylisoquinoline,benzyl-isoquinoline and protoberberine.Their cardiovascular effects were studied involving α-adrenoceptor,adenosine A_1,A_2 and DPH-calcium channel radioreceptor assays.In addition,calmodulin inhibiting,calcium antagonistic potassium channel blocking and antiplatelet aggre- gation activities were also performed.It was found that compound VI_(19) was a new potassium channe blocker with α-adrenoceptor antagonism,compound V_9,and V_(21) lowered blood pressure on various animal models with negative chronotropic action,compound VI_(13)possessed antiarrhythmic and antifi- brillation action,and it may be a candidate tot clinic evaluation.The structure-activity relationships deduced may provide a theoretical basis for further development of new agents.展开更多
A redox‐neutral avenue to access isoquinolines has been realized by a Co（III）‐catalyzed C–H activa‐tion process. Starting from readily available N‐sulfinyl imine substrates and alkynes, the reaction occurred vi...A redox‐neutral avenue to access isoquinolines has been realized by a Co（III）‐catalyzed C–H activa‐tion process. Starting from readily available N‐sulfinyl imine substrates and alkynes, the reaction occurred via N–S cleavage with broad substrate scope and functional group compatibility in the presence of cost‐effective cobalt catalysts.展开更多
The reaction of 1-methylisoquinoline 1 with hy-drazonoyl halides 2 in ethanol in the presence of chitosan under microwave irradiation affords triazoloisoquinoline 4. Product 4 reacts with dimethylformamide-dimethylace...The reaction of 1-methylisoquinoline 1 with hy-drazonoyl halides 2 in ethanol in the presence of chitosan under microwave irradiation affords triazoloisoquinoline 4. Product 4 reacts with dimethylformamide-dimethylacetal to give ena- minones 7 which react with hydrazonoyl halides to give pyrazolyl triazoloisoquinoline 13. Also, 1-methylisoquinoline 1 reacts with arylisothio-cyanate to give thioanilide 15 which reacts with hydrazonoyl halides to give the corresponding thiadiazolyl isoquinoline derivatives 20, 24.展开更多
The pyrolysis mechanisms of quinoline and isoquinoline were investigated using the density functional theory of quantum chemistry,including eight reaction paths and a common tautomeric intermediate 1-indene imine.It i...The pyrolysis mechanisms of quinoline and isoquinoline were investigated using the density functional theory of quantum chemistry,including eight reaction paths and a common tautomeric intermediate 1-indene imine.It is concluded that the conformational tautomerism of the intermediate decides the pyrolysis products(C6H6,HC≡C—C≡N,C6H5C≡N and HC≡CH)to be the same,and also decides the total disappearance rates of the reactants to be the same,for both original reactants quinoline and isoquinoline during the pyrolysis reaction.The results indicate that the intramolecular hydrogen migration is an important reaction step,which often appears in the paths of the pyrolysis mechanism.The activation energies of the rate determining steps are obtained.The calculated results are in good agreement with the experimental results.展开更多
Magnoline（1）,a new isoquinoline derivative,was isolated from the leaves of Magnolia sieboldii K.Koch（Magnoliaceae）.Its structure was elucidated on the basis of spectral analysis including 1D,2D NMR and HR-TOF-MS.
Mahonia leschenaultia（ML） and Mahonia napaulensis（MN） are less known and unexplored medicinal plants of the family Berberidaceae. They are used by the Todas of Nilgiris in their religious and medical practices but...Mahonia leschenaultia（ML） and Mahonia napaulensis（MN） are less known and unexplored medicinal plants of the family Berberidaceae. They are used by the Todas of Nilgiris in their religious and medical practices but chemically less identified. Hence, we decided to do extensive phytochemical analysis to explore the potential of these plant extracts. An ultrahigh performance electrospray tandem mass spectrometry（UHPLC-ESI-MS/MS）method was successfully developed for qualitative analysis of the bioactive components in Mahonia species using Orbitrap Velos Pro mass spectrometer. Sixteen compounds were identified by comparison of their retention times and mass spectra（MS） with authentic standards and reported literature. Multi-stage mass spectra（MS（2-8）） for the identification of protoberberine and aporphine alkaloids showed the sequential expulsion of all the substituents attached with their basic skeleton followed by CO loss. Eight of the identified compounds（berberine, jatrorrhizine, palmatine, magnoflorine, isocorydine, glaucine, tetrahydropalmatine and tetrahydroberberine） were simultaneously determined by another UHPLC-ESI-MS/MS method under the multiple reactions monitoring（MRM） mode quantitatively using triple quadrupole linear ion trap mass spectrometer. The analytical method was validated for 8 bioactive compounds with overall recovery in the range98.5%-103.6%（RSD≤2.2%）, precise（RSD≤2.07%） and linear（r≥0.9995） over the concentration range of 0.5-1000 ng/mL and successfully applied in ML and MN roots, which suggests the suitability of the proposed approach for the routine analysis of Mahonia species and their quality control.展开更多
An expedient,synthetic method to fused polycyclic derivatives of isoquinoline is described via tandem reaction of isoquinoline,dialkyl acetylenedicarboxylates and dialkyl chloromalonate.
One undescribedamide,pipermullesine A,twoundescribed isoquinoline alkaloids,pipermullesinesBand C,and six undescribed dipeptides,pipermullamides A–F,along with 28 known compounds,were isolated from the aerial parts o...One undescribedamide,pipermullesine A,twoundescribed isoquinoline alkaloids,pipermullesinesBand C,and six undescribed dipeptides,pipermullamides A–F,along with 28 known compounds,were isolated from the aerial parts of Piper mullesua.The structures of the undescribed compounds were elucidated based on the analysis of 1D and 2D NMR and MS data.Furthermore,the structures of pipermullesines A–Cwere confirmed by single crystal X-ray diffraction analysis.All isolates were evaluated for inhibitory activity against platelet aggregation induced by thrombin(IIa)or platelet-activating factor(PAF).(-)-Mangochinine,pellitorine,and(2E,4E)-N-isobutyl-2,4-dodecadienamide showed weak inhibitory activity against rabbit platelet aggregation induced by PAF,with IC_(50)values of 470.3μg/mL,614.9μg/mL,and 579.7μg/mL,respectively.展开更多
Isoquinoline reacts with dialkyl acetylenedicarboxylates in the presence of kojic acid or8-hydroxyquinoline to generate 1,2-dihydroisoquinoline derivatives. The simplicity, mild reaction conditions and high yields of ...Isoquinoline reacts with dialkyl acetylenedicarboxylates in the presence of kojic acid or8-hydroxyquinoline to generate 1,2-dihydroisoquinoline derivatives. The simplicity, mild reaction conditions and high yields of products make it an interesting process compared to other approaches. The compounds have been analyzed for antibacterial activity against Gram negative and Gram positive bacteria. The results indicated that 1,2-dihydroisoquinolines derived from kojic acid are effective against all of the studied bacteria especially against Bacillus subtilis, while the products obtained from8-hydroxyquinoline are active only against Gram positive bacteria.展开更多
An operationally simple and eco-friendly protocol has been developed for the synthesis of N-sulfonyl- 1,2,3,4-tetrahydroisoquinolines 3 using the modified Pictet-Spengler reaction of N-sulfonylphenylethy- lamines 1 an...An operationally simple and eco-friendly protocol has been developed for the synthesis of N-sulfonyl- 1,2,3,4-tetrahydroisoquinolines 3 using the modified Pictet-Spengler reaction of N-sulfonylphenylethy- lamines 1 and various aldehydes 2 in the presence of tungstophosphoric acid hydrate.展开更多
An effective route to 5-vinylated and N-vinylated benzo[d]oxazole-2（3H）-thiones and benzo[d]thiazole-2（3H）-thiones is described via reaction of acetylenic esters and benzo[d]oxazole-2-thiol and benzo[d]thiazole-2-...An effective route to 5-vinylated and N-vinylated benzo[d]oxazole-2（3H）-thiones and benzo[d]thiazole-2（3H）-thiones is described via reaction of acetylenic esters and benzo[d]oxazole-2-thiol and benzo[d]thiazole-2-thiol in the presence of 15 mol%of isoquinoline.展开更多
Two new isoquinoline alkaloids: carcrisine A and B, have been isolated from the whole plant of Carduus crispus L.. Their structures were elucidated by chemical and spectroscopic methods.
A one-pot sequential reaction for efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a]quinoline derivatives has been developed.The reaction included firstly the Cu-catalyzed three-component reaction of...A one-pot sequential reaction for efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a]quinoline derivatives has been developed.The reaction included firstly the Cu-catalyzed three-component reaction of isoquinoline（quinoline）,acetylenedicarboxylate and alkynylbenzene and then Cs 2 CO 3-promoted intramolecular cyclization reaction of initially formed 1-alkenyl-2-alkynyl-1,2-dihydroisoquinoline（1,2-dihydroquinoline）.展开更多
Two series of novel compounds designed as hybrids of 1-arylnaphthalene lignans with dihydroisoquinolines or isoquinolines were synthesized and evaluated for their cytotoxicities on human tumor cell lines, such as A549...Two series of novel compounds designed as hybrids of 1-arylnaphthalene lignans with dihydroisoquinolines or isoquinolines were synthesized and evaluated for their cytotoxicities on human tumor cell lines, such as A549, Hela, PC-3 and KB. Some of the synthetic compounds exhibited their IC50 values on selected cell lines at μmol/L scale.展开更多
A novel palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids is described,which provides a facile approach to access indolo[2,1-a]isoquinoline scaffolds.This metho...A novel palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids is described,which provides a facile approach to access indolo[2,1-a]isoquinoline scaffolds.This method employs benzene-1,3,5-triyl triformate(TFBen)as the CO surrogate for the incorporation of a carbonyl group into indolo[2,1-a]isoquinoline scaffolds,and a variety of carbonyl-containing indolo[2,1-a]isoquinoline derivatives are prepared in good yields.展开更多
Two 2-aryl imidazo [2,1-a] isoquinolines were synthesized and tested for pregnancy terminating activities. Both of them are new compounds and their structures were confirmed by IR, (HNMR)-H-1, MS and elemental analysi...Two 2-aryl imidazo [2,1-a] isoquinolines were synthesized and tested for pregnancy terminating activities. Both of them are new compounds and their structures were confirmed by IR, (HNMR)-H-1, MS and elemental analysis. They both showed high activities in NIH mice.展开更多
The development of anticancer drugs to treat triple-negative breast cancer(TNBC)is an ongoing challenge.Immunogenic cell death(ICD)has garnered considerable interest worldwide as a promising synergistic modality for c...The development of anticancer drugs to treat triple-negative breast cancer(TNBC)is an ongoing challenge.Immunogenic cell death(ICD)has garnered considerable interest worldwide as a promising synergistic modality for cancer chemoimmunotherapy.However,only few drugs or treatment modalities can trigger an ICD response and none of them exert a considerable clinical effect against TNBC.Therefore,new agents with potentially effective chemoimmunotherapeutic response are required.In this study,five new cyclometalated Ir(III)complexes containing isoquinoline alkaloid C^N ligands were designed and synthesized.Among them,Ir-1 exhibited the highest in vitro cytotoxicity.Mechanistically,Ir-1 could trigger autophagy-dependent ferroptosis and a subsequent ferroptosis-dependent ICD response as well as indoleamine 2,3-dioxygenase(IDO)inhibition via reactive oxygen species(ROS)-mediated endoplasmic reticulum(ER)stress in MDA-MB-231 cells.When immunocompetent BALB/c mice were vaccinated with Ir-1-treated dying TNBC cells,antitumor CD8^(+)T-cell response and Foxp3^(+)T-cell depletion were induced,resulting in long-lasting antitumor immunity in TNBC cells.Moreover,combination therapy with Ir-1 and anti-PD1 could substantially augment in vivo therapeutic effects.Based on these results,Ir-1 is a promising candidate for chemoimmunotherapy against TNBC and its effects are mediated synergistically via ICD induction and IDO blockage.展开更多
Catalytic asymmetric hydrophosphination of unsaturated substrates has been proven to be one of the most straightforward ways to achieve chiral phosphine compounds.Although the methodologies of transition metals and or...Catalytic asymmetric hydrophosphination of unsaturated substrates has been proven to be one of the most straightforward ways to achieve chiral phosphine compounds.Although the methodologies of transition metals and organocatalysts catalyzed enantioselective hydrophosphination reactions have been well developed during the last decade,the enantioselective construction of quinoline and isoquinoline-based phosphines remains challenging.Furthermore,the chiral quinoline-based phosphines play a significant role in the preparation of chiral P,N-ligands.Herein,we report a comprehensive investigation for the asymmetric addition of diarylphosphine oxides to a wide range ofα,β-unsaturated quinolines and isoquinolines,catalyzed by commercial chiral phosphoric acid,affording the corresponding products with up to 99%yield and 98%ee.展开更多
基金the Tianshan Talents Program for Leading Talents in Science and Technology Innovation(No.2022TSYCLJ0016)the National Natural Science Foundation of China(Nos.21961037 and 22201241)+3 种基金the Program for Tianshan Innovative Research Team of Xinjiang Uygur Autonomous Region(No.2021D14011)the Graduate Innovation Project of Xinjiang Uygur Autonomous Region(No.XJ2021G036)the Key Program of Natural Science Foundation of Xinjiang Uygur Autonomous Region(No.2022D01D06)the Natural Science Foundation of Xinjiang Uygur Autonomous Region(Nos.2021D01E10 and 2022E01042).
文摘Photocatalytic and photoinduced silyl radicals cascade cyclization procedures for the green and simple preparation of fused tetracyclic skeleton silylated indolo[2,1-a]isoquinoline-6(5H)-ones from 2-aryl-N-acryloyl indoles with hydrosilanes are developed.The photocatalytic reaction is carried out with 9,10-dicyanoanthracene(DCA)as an organophotocatalyst and 3-acetoxyquinuclidine as hydrogen atom transfer(HAT)catalyst at room temperature under metal-and oxidant-free conditions.The keys to the success of photoredox-catalytic conversion include(1)the reductive quenching of DCA^(*)[E_(1/2)(*P/P^(-))=+1.97 V vs.SCE in MeCN]by 3-acetoxyquinuclidine(E_(p)=+1.22 V vs.SCE in MeCN),and(2)the thermodynamic feasibility of hydrogen atom abstraction from hydridic Si-H bond by electrophilic N^(+·).Particularly,the simple photoinduced cascade cyclization using(TMS)3SiH with 2-aryl-N-acryloyl indoles was exploited via an electron-donor-acceptor(EDA)complex under visible light irradiation.
基金supported by National Key R&D Program of China(2022YFF1100301)Major Science and Technology Project of Henan Province(231100310200)+1 种基金Yunnan Applied Basic Research Projects(202301AS070057)Yunnan Science and Technology Department(202305AH340005),DR PLANT.
文摘Four new isoquinoline alkaloids,hypecotumines A-D(1-4),were isolated and identified from the whole herbs of Hypecoum erectum L.Their structures were determined by a combination of HRESIMS,NMR,and X-ray diffraction analysis methods.Compounds 1-4 were characterized by a terminal double bond at C-9 and their plausible biosynthetic pathway was hypothesized.Since PCSK9 plays a key role in the development of cardiovascular disease(CVD),exploration of PCSK inhibitors from natural products are beneficial for drug discovery of CVD treatment.SPR and Western blot assays showed compound 4 had PCSK9 inhibition activity with KD value of 59.9μM and thus elevated the LDLR level.Further molecular docking studies demonstrated that 4 and PCSK9 could form stable interactions via key hydrogen bonds.
文摘By using active principles of Chinese medicinal materials as lead compounds soquinoline derivatives have been designed and synthesized.Their chemical structures include bisbenzylisoquinoline,benzyl-isoquinoline and protoberberine.Their cardiovascular effects were studied involving α-adrenoceptor,adenosine A_1,A_2 and DPH-calcium channel radioreceptor assays.In addition,calmodulin inhibiting,calcium antagonistic potassium channel blocking and antiplatelet aggre- gation activities were also performed.It was found that compound VI_(19) was a new potassium channe blocker with α-adrenoceptor antagonism,compound V_9,and V_(21) lowered blood pressure on various animal models with negative chronotropic action,compound VI_(13)possessed antiarrhythmic and antifi- brillation action,and it may be a candidate tot clinic evaluation.The structure-activity relationships deduced may provide a theoretical basis for further development of new agents.
基金supported by the Dalian Institute of Chemical Physics,Chinese Academy of Sciencesthe National Natural Science Foundation of China (21272231)~~
文摘A redox‐neutral avenue to access isoquinolines has been realized by a Co（III）‐catalyzed C–H activa‐tion process. Starting from readily available N‐sulfinyl imine substrates and alkynes, the reaction occurred via N–S cleavage with broad substrate scope and functional group compatibility in the presence of cost‐effective cobalt catalysts.
文摘The reaction of 1-methylisoquinoline 1 with hy-drazonoyl halides 2 in ethanol in the presence of chitosan under microwave irradiation affords triazoloisoquinoline 4. Product 4 reacts with dimethylformamide-dimethylacetal to give ena- minones 7 which react with hydrazonoyl halides to give pyrazolyl triazoloisoquinoline 13. Also, 1-methylisoquinoline 1 reacts with arylisothio-cyanate to give thioanilide 15 which reacts with hydrazonoyl halides to give the corresponding thiadiazolyl isoquinoline derivatives 20, 24.
基金Supported by the National Basic Research Program of China （2005CB221203）, the National Natural Science Foundation of China （20576087, 20776093） and the Foundation of Shanxi Province （2006011022, 2009021015）.
文摘The pyrolysis mechanisms of quinoline and isoquinoline were investigated using the density functional theory of quantum chemistry,including eight reaction paths and a common tautomeric intermediate 1-indene imine.It is concluded that the conformational tautomerism of the intermediate decides the pyrolysis products(C6H6,HC≡C—C≡N,C6H5C≡N and HC≡CH)to be the same,and also decides the total disappearance rates of the reactants to be the same,for both original reactants quinoline and isoquinoline during the pyrolysis reaction.The results indicate that the intramolecular hydrogen migration is an important reaction step,which often appears in the paths of the pyrolysis mechanism.The activation energies of the rate determining steps are obtained.The calculated results are in good agreement with the experimental results.
文摘Magnoline（1）,a new isoquinoline derivative,was isolated from the leaves of Magnolia sieboldii K.Koch（Magnoliaceae）.Its structure was elucidated on the basis of spectral analysis including 1D,2D NMR and HR-TOF-MS.
文摘Mahonia leschenaultia（ML） and Mahonia napaulensis（MN） are less known and unexplored medicinal plants of the family Berberidaceae. They are used by the Todas of Nilgiris in their religious and medical practices but chemically less identified. Hence, we decided to do extensive phytochemical analysis to explore the potential of these plant extracts. An ultrahigh performance electrospray tandem mass spectrometry（UHPLC-ESI-MS/MS）method was successfully developed for qualitative analysis of the bioactive components in Mahonia species using Orbitrap Velos Pro mass spectrometer. Sixteen compounds were identified by comparison of their retention times and mass spectra（MS） with authentic standards and reported literature. Multi-stage mass spectra（MS（2-8）） for the identification of protoberberine and aporphine alkaloids showed the sequential expulsion of all the substituents attached with their basic skeleton followed by CO loss. Eight of the identified compounds（berberine, jatrorrhizine, palmatine, magnoflorine, isocorydine, glaucine, tetrahydropalmatine and tetrahydroberberine） were simultaneously determined by another UHPLC-ESI-MS/MS method under the multiple reactions monitoring（MRM） mode quantitatively using triple quadrupole linear ion trap mass spectrometer. The analytical method was validated for 8 bioactive compounds with overall recovery in the range98.5%-103.6%（RSD≤2.2%）, precise（RSD≤2.07%） and linear（r≥0.9995） over the concentration range of 0.5-1000 ng/mL and successfully applied in ML and MN roots, which suggests the suitability of the proposed approach for the routine analysis of Mahonia species and their quality control.
基金Sanandaj Branch, Islamic Azad University Research Council for the fnancial support of this research
文摘An expedient,synthetic method to fused polycyclic derivatives of isoquinoline is described via tandem reaction of isoquinoline,dialkyl acetylenedicarboxylates and dialkyl chloromalonate.
基金This work was funded by the Southeast Asia Biodiversity Research Institute,Chinese Academy of Sciences(Y4ZK111B01)the Natural Science Foundation of Yunnan Province,China(2011FZ205)+2 种基金the International Partneship Program of Chinese Academy of Sciences(153631KYSB20160004)the Key Laboratory of Ethnomedicine(Minzu University of China)of Ministry of Education of China(KLEM-ZZ201806)the National Natural Science Foundation of China(31761143001&31161140345).
文摘One undescribedamide,pipermullesine A,twoundescribed isoquinoline alkaloids,pipermullesinesBand C,and six undescribed dipeptides,pipermullamides A–F,along with 28 known compounds,were isolated from the aerial parts of Piper mullesua.The structures of the undescribed compounds were elucidated based on the analysis of 1D and 2D NMR and MS data.Furthermore,the structures of pipermullesines A–Cwere confirmed by single crystal X-ray diffraction analysis.All isolates were evaluated for inhibitory activity against platelet aggregation induced by thrombin(IIa)or platelet-activating factor(PAF).(-)-Mangochinine,pellitorine,and(2E,4E)-N-isobutyl-2,4-dodecadienamide showed weak inhibitory activity against rabbit platelet aggregation induced by PAF,with IC_(50)values of 470.3μg/mL,614.9μg/mL,and 579.7μg/mL,respectively.
文摘Isoquinoline reacts with dialkyl acetylenedicarboxylates in the presence of kojic acid or8-hydroxyquinoline to generate 1,2-dihydroisoquinoline derivatives. The simplicity, mild reaction conditions and high yields of products make it an interesting process compared to other approaches. The compounds have been analyzed for antibacterial activity against Gram negative and Gram positive bacteria. The results indicated that 1,2-dihydroisoquinolines derived from kojic acid are effective against all of the studied bacteria especially against Bacillus subtilis, while the products obtained from8-hydroxyquinoline are active only against Gram positive bacteria.
基金the research grant from Srinakharinwirot University(B.E.2555)supported by Offce of the Higher Education CommissionMahidol University under the National Research Universities Initiative
文摘An operationally simple and eco-friendly protocol has been developed for the synthesis of N-sulfonyl- 1,2,3,4-tetrahydroisoquinolines 3 using the modified Pictet-Spengler reaction of N-sulfonylphenylethy- lamines 1 and various aldehydes 2 in the presence of tungstophosphoric acid hydrate.
文摘An effective route to 5-vinylated and N-vinylated benzo[d]oxazole-2（3H）-thiones and benzo[d]thiazole-2（3H）-thiones is described via reaction of acetylenic esters and benzo[d]oxazole-2-thiol and benzo[d]thiazole-2-thiol in the presence of 15 mol%of isoquinoline.
文摘Two new isoquinoline alkaloids: carcrisine A and B, have been isolated from the whole plant of Carduus crispus L.. Their structures were elucidated by chemical and spectroscopic methods.
基金Supported by the National Natural Science Foundation of China(No.21172189)
文摘A one-pot sequential reaction for efficient synthesis of pyrrolo[2,1-a]isoquinoline and pyrrolo[1,2-a]quinoline derivatives has been developed.The reaction included firstly the Cu-catalyzed three-component reaction of isoquinoline（quinoline）,acetylenedicarboxylate and alkynylbenzene and then Cs 2 CO 3-promoted intramolecular cyclization reaction of initially formed 1-alkenyl-2-alkynyl-1,2-dihydroisoquinoline（1,2-dihydroquinoline）.
文摘Two series of novel compounds designed as hybrids of 1-arylnaphthalene lignans with dihydroisoquinolines or isoquinolines were synthesized and evaluated for their cytotoxicities on human tumor cell lines, such as A549, Hela, PC-3 and KB. Some of the synthetic compounds exhibited their IC50 values on selected cell lines at μmol/L scale.
基金the financial supports from the Joint Funds of the Zhejiang Provincial Natural Science Foundation of China(No.LTY21B020001)the Fundamental Research Funds of Zhejiang Sci-Tech University(No.2021Q052)。
文摘A novel palladium-catalyzed carbonylative cyclization of alkene-tethered indoles with phenols or arylboronic acids is described,which provides a facile approach to access indolo[2,1-a]isoquinoline scaffolds.This method employs benzene-1,3,5-triyl triformate(TFBen)as the CO surrogate for the incorporation of a carbonyl group into indolo[2,1-a]isoquinoline scaffolds,and a variety of carbonyl-containing indolo[2,1-a]isoquinoline derivatives are prepared in good yields.
文摘Two 2-aryl imidazo [2,1-a] isoquinolines were synthesized and tested for pregnancy terminating activities. Both of them are new compounds and their structures were confirmed by IR, (HNMR)-H-1, MS and elemental analysis. They both showed high activities in NIH mice.
基金supported by the National Natural Science Foundation of China(22177022,22267005)the Natural Science Foundation of Guangxi Province of China(AD22035193).
文摘The development of anticancer drugs to treat triple-negative breast cancer(TNBC)is an ongoing challenge.Immunogenic cell death(ICD)has garnered considerable interest worldwide as a promising synergistic modality for cancer chemoimmunotherapy.However,only few drugs or treatment modalities can trigger an ICD response and none of them exert a considerable clinical effect against TNBC.Therefore,new agents with potentially effective chemoimmunotherapeutic response are required.In this study,five new cyclometalated Ir(III)complexes containing isoquinoline alkaloid C^N ligands were designed and synthesized.Among them,Ir-1 exhibited the highest in vitro cytotoxicity.Mechanistically,Ir-1 could trigger autophagy-dependent ferroptosis and a subsequent ferroptosis-dependent ICD response as well as indoleamine 2,3-dioxygenase(IDO)inhibition via reactive oxygen species(ROS)-mediated endoplasmic reticulum(ER)stress in MDA-MB-231 cells.When immunocompetent BALB/c mice were vaccinated with Ir-1-treated dying TNBC cells,antitumor CD8^(+)T-cell response and Foxp3^(+)T-cell depletion were induced,resulting in long-lasting antitumor immunity in TNBC cells.Moreover,combination therapy with Ir-1 and anti-PD1 could substantially augment in vivo therapeutic effects.Based on these results,Ir-1 is a promising candidate for chemoimmunotherapy against TNBC and its effects are mediated synergistically via ICD induction and IDO blockage.
基金supported by the National Natural Science Foundation of China(22361053)Yunnan Fundamental Research Projects(202301AU070125,202401BC070018)+1 种基金Scientific Research of Department of Education for Yunnan Province(2025Y0679)Yunnan Key Laboratory of Chiral Functional Substance Research and Application(202402AN360010).
文摘Catalytic asymmetric hydrophosphination of unsaturated substrates has been proven to be one of the most straightforward ways to achieve chiral phosphine compounds.Although the methodologies of transition metals and organocatalysts catalyzed enantioselective hydrophosphination reactions have been well developed during the last decade,the enantioselective construction of quinoline and isoquinoline-based phosphines remains challenging.Furthermore,the chiral quinoline-based phosphines play a significant role in the preparation of chiral P,N-ligands.Herein,we report a comprehensive investigation for the asymmetric addition of diarylphosphine oxides to a wide range ofα,β-unsaturated quinolines and isoquinolines,catalyzed by commercial chiral phosphoric acid,affording the corresponding products with up to 99%yield and 98%ee.
