In this work it was presented an application of task specific onium salt as soluble support for the synthesis of 3-amino-5-aryl-2,5- dihydropyridazines. This soluble support is of wide applicability and combines advan...In this work it was presented an application of task specific onium salt as soluble support for the synthesis of 3-amino-5-aryl-2,5- dihydropyridazines. This soluble support is of wide applicability and combines advantages of solid phase synthesis without its limitations with those of solution phase chemistry. After a simple washing step, products were cleaved from the supports and obtained in good yields.展开更多
This report describes a new three‐component strategy for the regioselective synthesis of a series of tri‐substituted pyridazines via a 1,4‐diazabicyclo[2.2.2]octane （DABCO）‐catalyzed condensation of propiophenon...This report describes a new three‐component strategy for the regioselective synthesis of a series of tri‐substituted pyridazines via a 1,4‐diazabicyclo[2.2.2]octane （DABCO）‐catalyzed condensation of propiophenones, arylglyoxalmonohydrates and hydrazine hydrate in water. This method provides a green and convenient one‐pot route toward a diverse set of 3,6‐diaryl‐4‐methylpyridazines bearing various aryl substituents. This procedure is highly regioselective, operationally simple, uses water as a safe, environmentally friendly solvent, and DABCO as a green base‐organocatalyst, and affords good to excellent yields of products.展开更多
Pyridazine has garnered increasing attention as a privileged scaffold and bioisosterism in drug discovery due to its unique structural characteristics.It can serve as a hydrogen bond acceptor when interacting with rec...Pyridazine has garnered increasing attention as a privileged scaffold and bioisosterism in drug discovery due to its unique structural characteristics.It can serve as a hydrogen bond acceptor when interacting with receptors due to its two adjacent nitrogen atoms.Upon conversion to pyridazinone,it exhibits the ability to act as both a hydrogen bond acceptor and donor,showcasing its versatility.This inherent flexibility has prompted extensive research exploring its bioactivity in pesticides and pharmaceuticals.In order to promote the development of pyridazine-based pesticides,this review provides a comprehensive summary of advancements for pyridazine-based pesticides on herbicidal(36.9%),insecticidal(26.2%),antifungal and antibacterial(24.6%),plant growth regulatory(10.8%),and antiviral activities(1.5%)from2000 to 2024.It serves as an invaluable reference and source of inspiration for agricultural scientists conducting future research.展开更多
O6-Corona[3]arene[3]pyridazines were synthesized from the one-pot macrocyclic condensation reaction of 3,6-dichlorotetrazine with 1,4-dihydroquinone derivatives followed by the inverse electron demand Diels-Alder reac...O6-Corona[3]arene[3]pyridazines were synthesized from the one-pot macrocyclic condensation reaction of 3,6-dichlorotetrazine with 1,4-dihydroquinone derivatives followed by the inverse electron demand Diels-Alder reaction of the tetrazine rings with a cyclopentanone-derived enamine. Conversion of six ester groups within macrocycle into all sodium acetate moieties afforded a water soluble O6-corona[3]arene[3]pyridazine. The coronary macrocycle host formed complexes selectively with organic ammoniums and dinitrile vips in a 1 ： 1 stoichiometric ratio in organic solvents with association constants ranging from （2.96± 0.10）× 10^1 to （2.53±0.33）× 10^5 L·mol^-1. Water soluble O6-corona[3]arene[3]pyridazine was also able to complex strongly with organic ammoniums in water to give an association constant up to （2.67 ± 0.21） × 10^4 L·mol^-1. The pseudo-rotaxane and inclusion structures of the host-vip complexes were revealed by the X-ray crystallography.展开更多
In searching for effective anticonvulsant agents,fourteen 6-aryl-4.5-di- hydro-3(2H)pyridazinones.fifteen 6-aryl-3(2H)pyridazinones,and seventeen 3-GABA derivatives of 6-aryIpyridazines have been synthesized,and evalu...In searching for effective anticonvulsant agents,fourteen 6-aryl-4.5-di- hydro-3(2H)pyridazinones.fifteen 6-aryl-3(2H)pyridazinones,and seventeen 3-GABA derivatives of 6-aryIpyridazines have been synthesized,and evaluated in mice for the ability to antagonize maximal electroshock seizure(MES).The ED_(50) values showed that 6-(2′,4′- dichlorophenyt)-3(2H)pyridazinone was the most potent anticonvulsant among these corn- pounds(ED_(50)=10.15 mg/kg).The structure-activity relationships of the aryl pyridazinones were studied.The result showed that:(1)the higher the value of the hydrophobic parameter л of the substituent on the phenyl ring.the more potent the anticonvulsant activity of the corn- pound.and(2)only the compounds with an electron withdrawing substituent on the phenyl ring exhibited appreciable anticonvulsant activity.展开更多
Many studies have been performed on the pyridazine(1,2-diazine) derivatives in the past decade. This heterocyclic nucleus possesses almost all types of pharmacological activities. This small and simple pyridazine nucl...Many studies have been performed on the pyridazine(1,2-diazine) derivatives in the past decade. This heterocyclic nucleus possesses almost all types of pharmacological activities. This small and simple pyridazine nucleus is present in various compounds that are involved in the research aiming to evaluate new compounds with interesting biological activities, including anti-bacterial, anti-fungal, anti-viral, analgesic, anti-inflammatory, anti-platelets, anti-ulcer, anti-secretory, anti-depressants, anxiolytics, sedative-hypnotics, anti-convulsant, anti-tumor, anti-thrombotics, cardiotonics, vasodilatators, anti-arrhythmics, anti-diabetic, anti-tubercular agents and so on. This review focuses on the pyridazine derivatives with potential activities that have been developed. Pyridazine compounds draw attention of scientists and researchers because of their diverse biological activities as well as simple chemical and easy functionalization at various ring positions, making them attractive synthetic building blocks for designing and development of novel pyridazinone-based therapeutic agents.展开更多
The title compound, Co（L）2（CH3OH）2Cl2 （L = 3-（1,2,4-triazole-yl）-6-chloro-pyridazine） 1, has been synthesized and its crystal structure has been determined by X-ray analysis. Complex 1 crystallizes in the tric...The title compound, Co（L）2（CH3OH）2Cl2 （L = 3-（1,2,4-triazole-yl）-6-chloro-pyridazine） 1, has been synthesized and its crystal structure has been determined by X-ray analysis. Complex 1 crystallizes in the triclinic system, space group P1 with a = 6.018（3）, b = 9.832（5）, c = 9.921（5）A, a = 78.270（8）, β = 74.550（8）, γ = 83.807（8）°, V = 553.1（5）A^3, Z = 1, C14H16Cl4CoN10O2, Mr = 557.10, Dc = 1.673 g/cm^3, F（000） = 281,μ（MoKα） = 1.293 mm^-1, the final R = 0.0453 and wR = 0.1181 for 1539 observed reflections with I 〉 2σ（I）. The Co（II） ion is in a distorted centrosymmetric six-coordinate octahedral environment with two Ntriazole, two Omethanol and two Cl atoms. Via hydrogen bonds the configuration of 1 has been extended into 1D chains which are developed to 2D layers via π-π sticking action, and these layers are further extended into a 3D network by hydrogen bonds. The antibacterial activity of the title compound has been detected, and the results show that the ligands and cobalt（II） complex exhibit certain fungicidal activity against several bacteria. Furthermore, the spectral properties of the title compound have been also studied and discussed.展开更多
A three-dimensional（3D） coordination polymer,[Cd（SC）（DPPD）]_n（1,H_2SC = succinic acid and DPPD = 3,6-di（4-pyridyl）pyridazine）,has been synthesized by the solvothermal reaction of Cd（NO_3）_2·4H_2O with...A three-dimensional（3D） coordination polymer,[Cd（SC）（DPPD）]_n（1,H_2SC = succinic acid and DPPD = 3,6-di（4-pyridyl）pyridazine）,has been synthesized by the solvothermal reaction of Cd（NO_3）_2·4H_2O with H_2 SC and DPPD at 120 ℃ in DMF solvent. Compound 1 crystallizes in the monoclinic system,space group P2_1/c,with a = 10.7993（4）,b = 11.7705（3）,c = 13.5336（6） A,V = 1678.89（11） A^3,Z = 4,C18H14N4O_4 Cd,M_r = 462.73,D_c = 1.831 g/cm^3,μ = 1.335 mm^（-1）,F（000） = 920.0,the final R = 0.0500 and wR = 0.1567 for 3714 observed reflections with I 〉 2s（I）. In compound 1,the Cd（Ⅱ） ions are linked by the SC^2– ligands to give a two-dimensional（2D） undulating sheet based on the centrosymmetric dinuclear Cd_2（COO）_2 units. The 2D sheets are further connected by the DPPD ligands to produce a 3D structure,which is a 6-connected（4^4·6·^10·8） topological network based on the dinuclear Cd_2（COO）_2 node. Compound 1 exhibits a photoluminescent emission with a maximum at 540 nm upon excitation at 460 nm.展开更多
The title compound 3-（4-bromobenzyloxy）-6-morpholinopyridazine（C15H16BrN3O2） was synthesized,and its crystal structure was studied.It crystallizes in the triclinic system,space group P with a = 8.3408（17）,b = 8....The title compound 3-（4-bromobenzyloxy）-6-morpholinopyridazine（C15H16BrN3O2） was synthesized,and its crystal structure was studied.It crystallizes in the triclinic system,space group P with a = 8.3408（17）,b = 8.8620（18）,c = 10.832（2） ,α = 108.09（3）,β = 91.28（3）,γ = 100.90（3）°,Dc = 1.562 g/cm3,Z = 2,λ = 0.71073 ,μ（MoKα） = 2.769 mm-1,Mr = 350.22,V = 744.5（3） 3,F（000） = 356,the final R = 0.0522 and wR = 0.1366 for 2016 observed reflections with I 〉 2σ（I）.In the crystal structure,the morpholine ring adopts a chair conformation with O（2） and N（3） atoms at the flap positions-0.656（7） and 0.622（6） out of the mean plane formed by the other four C atoms,respectively.These molecules generate centro-symmetric dimers through intermolecular π-π interaction.展开更多
Stable oxygen evolution reaction(OER)catalyst alternatives to the precious IrO_(2) catalysts are of great importance to the next-generation proton-exchange membrane(PEM)electrolyzers.RuO_(2)-based materials are promis...Stable oxygen evolution reaction(OER)catalyst alternatives to the precious IrO_(2) catalysts are of great importance to the next-generation proton-exchange membrane(PEM)electrolyzers.RuO_(2)-based materials are promising candidates but suffer from low stability under highly anodic potentials.Here,we reported a facet-selective etching strategy to improve the stability of polycrystalline RuO_(2) without significantly affecting the activity.The selective etching was enabled by the specific chemisorption of pyridazine(pyd)with contingent N atoms onto the RuO_(2) surface.The pyd-RuO_(2) catalyst,after etching,exhibited a low overpotential 247 mV at 100 mA·cm^(-2) and obvious stability improvement of over 200 h at 100 mA·cm^(-2) with only 0.63% Ru loss in acidic conditions.Combining various characterization techniques and theoretical calculations,we revealed that the crystalline RuO_(2)(110)facet is favorably etched by the coordination of pyridazine while protecting other surfaces,which significantly enriches the RuO_(2)(110)facets toward higher OER stability via the dynamic dissolution and repair mechanism in the ordered manner.This study offers alternative perspectives on the dissolution and stability mechanism of RuO_(2) and the facet-selective modulation of nanocrystals by ligand-driven etching.展开更多
基金the Natural Sciences Foundation of Hubei province in China(Nos.2007ABA031 and 2008CDA078)
文摘In this work it was presented an application of task specific onium salt as soluble support for the synthesis of 3-amino-5-aryl-2,5- dihydropyridazines. This soluble support is of wide applicability and combines advantages of solid phase synthesis without its limitations with those of solution phase chemistry. After a simple washing step, products were cleaved from the supports and obtained in good yields.
基金supported by the Research Council of Payame Noor University
文摘This report describes a new three‐component strategy for the regioselective synthesis of a series of tri‐substituted pyridazines via a 1,4‐diazabicyclo[2.2.2]octane （DABCO）‐catalyzed condensation of propiophenones, arylglyoxalmonohydrates and hydrazine hydrate in water. This method provides a green and convenient one‐pot route toward a diverse set of 3,6‐diaryl‐4‐methylpyridazines bearing various aryl substituents. This procedure is highly regioselective, operationally simple, uses water as a safe, environmentally friendly solvent, and DABCO as a green base‐organocatalyst, and affords good to excellent yields of products.
基金the financial support from the National Key Research and Development Program of China(No.2021YFD1700102)the National Natural Science Foundation of China(No.32472608)+3 种基金the Guizhou Provincial Fundation for Excellent Scholars Program(No.GCC[2023]069)the Central Government Guides Local Science and Technology Development Fund Projects(No.Qiankehezhongyindi[2024]007)the Guizhou Province Program of Major Scientific and Technological(No.Qiankehechengguo[2024]zhongda007)the Central Government Guides Local Science and Technology Development Fund Projects(No.Qiankehezhongyindi(2023)001)。
文摘Pyridazine has garnered increasing attention as a privileged scaffold and bioisosterism in drug discovery due to its unique structural characteristics.It can serve as a hydrogen bond acceptor when interacting with receptors due to its two adjacent nitrogen atoms.Upon conversion to pyridazinone,it exhibits the ability to act as both a hydrogen bond acceptor and donor,showcasing its versatility.This inherent flexibility has prompted extensive research exploring its bioactivity in pesticides and pharmaceuticals.In order to promote the development of pyridazine-based pesticides,this review provides a comprehensive summary of advancements for pyridazine-based pesticides on herbicidal(36.9%),insecticidal(26.2%),antifungal and antibacterial(24.6%),plant growth regulatory(10.8%),and antiviral activities(1.5%)from2000 to 2024.It serves as an invaluable reference and source of inspiration for agricultural scientists conducting future research.
基金We also thank the National Natural Science Foundation of China （Nos. 21732004, 91427301, 21421064） and Tsinghua University for financial Support.
文摘O6-Corona[3]arene[3]pyridazines were synthesized from the one-pot macrocyclic condensation reaction of 3,6-dichlorotetrazine with 1,4-dihydroquinone derivatives followed by the inverse electron demand Diels-Alder reaction of the tetrazine rings with a cyclopentanone-derived enamine. Conversion of six ester groups within macrocycle into all sodium acetate moieties afforded a water soluble O6-corona[3]arene[3]pyridazine. The coronary macrocycle host formed complexes selectively with organic ammoniums and dinitrile vips in a 1 ： 1 stoichiometric ratio in organic solvents with association constants ranging from （2.96± 0.10）× 10^1 to （2.53±0.33）× 10^5 L·mol^-1. Water soluble O6-corona[3]arene[3]pyridazine was also able to complex strongly with organic ammoniums in water to give an association constant up to （2.67 ± 0.21） × 10^4 L·mol^-1. The pseudo-rotaxane and inclusion structures of the host-vip complexes were revealed by the X-ray crystallography.
文摘In searching for effective anticonvulsant agents,fourteen 6-aryl-4.5-di- hydro-3(2H)pyridazinones.fifteen 6-aryl-3(2H)pyridazinones,and seventeen 3-GABA derivatives of 6-aryIpyridazines have been synthesized,and evaluated in mice for the ability to antagonize maximal electroshock seizure(MES).The ED_(50) values showed that 6-(2′,4′- dichlorophenyt)-3(2H)pyridazinone was the most potent anticonvulsant among these corn- pounds(ED_(50)=10.15 mg/kg).The structure-activity relationships of the aryl pyridazinones were studied.The result showed that:(1)the higher the value of the hydrophobic parameter л of the substituent on the phenyl ring.the more potent the anticonvulsant activity of the corn- pound.and(2)only the compounds with an electron withdrawing substituent on the phenyl ring exhibited appreciable anticonvulsant activity.
文摘Many studies have been performed on the pyridazine(1,2-diazine) derivatives in the past decade. This heterocyclic nucleus possesses almost all types of pharmacological activities. This small and simple pyridazine nucleus is present in various compounds that are involved in the research aiming to evaluate new compounds with interesting biological activities, including anti-bacterial, anti-fungal, anti-viral, analgesic, anti-inflammatory, anti-platelets, anti-ulcer, anti-secretory, anti-depressants, anxiolytics, sedative-hypnotics, anti-convulsant, anti-tumor, anti-thrombotics, cardiotonics, vasodilatators, anti-arrhythmics, anti-diabetic, anti-tubercular agents and so on. This review focuses on the pyridazine derivatives with potential activities that have been developed. Pyridazine compounds draw attention of scientists and researchers because of their diverse biological activities as well as simple chemical and easy functionalization at various ring positions, making them attractive synthetic building blocks for designing and development of novel pyridazinone-based therapeutic agents.
文摘The title compound, Co（L）2（CH3OH）2Cl2 （L = 3-（1,2,4-triazole-yl）-6-chloro-pyridazine） 1, has been synthesized and its crystal structure has been determined by X-ray analysis. Complex 1 crystallizes in the triclinic system, space group P1 with a = 6.018（3）, b = 9.832（5）, c = 9.921（5）A, a = 78.270（8）, β = 74.550（8）, γ = 83.807（8）°, V = 553.1（5）A^3, Z = 1, C14H16Cl4CoN10O2, Mr = 557.10, Dc = 1.673 g/cm^3, F（000） = 281,μ（MoKα） = 1.293 mm^-1, the final R = 0.0453 and wR = 0.1181 for 1539 observed reflections with I 〉 2σ（I）. The Co（II） ion is in a distorted centrosymmetric six-coordinate octahedral environment with two Ntriazole, two Omethanol and two Cl atoms. Via hydrogen bonds the configuration of 1 has been extended into 1D chains which are developed to 2D layers via π-π sticking action, and these layers are further extended into a 3D network by hydrogen bonds. The antibacterial activity of the title compound has been detected, and the results show that the ligands and cobalt（II） complex exhibit certain fungicidal activity against several bacteria. Furthermore, the spectral properties of the title compound have been also studied and discussed.
基金Supported by the National Natural Science Foundation of China(No.21361011 and 21101081)Science Founds of State key Laboratory of Structural Chemistry(20130011)
文摘A three-dimensional（3D） coordination polymer,[Cd（SC）（DPPD）]_n（1,H_2SC = succinic acid and DPPD = 3,6-di（4-pyridyl）pyridazine）,has been synthesized by the solvothermal reaction of Cd（NO_3）_2·4H_2O with H_2 SC and DPPD at 120 ℃ in DMF solvent. Compound 1 crystallizes in the monoclinic system,space group P2_1/c,with a = 10.7993（4）,b = 11.7705（3）,c = 13.5336（6） A,V = 1678.89（11） A^3,Z = 4,C18H14N4O_4 Cd,M_r = 462.73,D_c = 1.831 g/cm^3,μ = 1.335 mm^（-1）,F（000） = 920.0,the final R = 0.0500 and wR = 0.1567 for 3714 observed reflections with I 〉 2s（I）. In compound 1,the Cd（Ⅱ） ions are linked by the SC^2– ligands to give a two-dimensional（2D） undulating sheet based on the centrosymmetric dinuclear Cd_2（COO）_2 units. The 2D sheets are further connected by the DPPD ligands to produce a 3D structure,which is a 6-connected（4^4·6·^10·8） topological network based on the dinuclear Cd_2（COO）_2 node. Compound 1 exhibits a photoluminescent emission with a maximum at 540 nm upon excitation at 460 nm.
文摘The title compound 3-（4-bromobenzyloxy）-6-morpholinopyridazine（C15H16BrN3O2） was synthesized,and its crystal structure was studied.It crystallizes in the triclinic system,space group P with a = 8.3408（17）,b = 8.8620（18）,c = 10.832（2） ,α = 108.09（3）,β = 91.28（3）,γ = 100.90（3）°,Dc = 1.562 g/cm3,Z = 2,λ = 0.71073 ,μ（MoKα） = 2.769 mm-1,Mr = 350.22,V = 744.5（3） 3,F（000） = 356,the final R = 0.0522 and wR = 0.1366 for 2016 observed reflections with I 〉 2σ（I）.In the crystal structure,the morpholine ring adopts a chair conformation with O（2） and N（3） atoms at the flap positions-0.656（7） and 0.622（6） out of the mean plane formed by the other four C atoms,respectively.These molecules generate centro-symmetric dimers through intermolecular π-π interaction.
基金supported by the National Natural Science Foundation of China(No.22172036)the Fundamental Research Funds for the Central Universities(No.20720220011).
文摘Stable oxygen evolution reaction(OER)catalyst alternatives to the precious IrO_(2) catalysts are of great importance to the next-generation proton-exchange membrane(PEM)electrolyzers.RuO_(2)-based materials are promising candidates but suffer from low stability under highly anodic potentials.Here,we reported a facet-selective etching strategy to improve the stability of polycrystalline RuO_(2) without significantly affecting the activity.The selective etching was enabled by the specific chemisorption of pyridazine(pyd)with contingent N atoms onto the RuO_(2) surface.The pyd-RuO_(2) catalyst,after etching,exhibited a low overpotential 247 mV at 100 mA·cm^(-2) and obvious stability improvement of over 200 h at 100 mA·cm^(-2) with only 0.63% Ru loss in acidic conditions.Combining various characterization techniques and theoretical calculations,we revealed that the crystalline RuO_(2)(110)facet is favorably etched by the coordination of pyridazine while protecting other surfaces,which significantly enriches the RuO_(2)(110)facets toward higher OER stability via the dynamic dissolution and repair mechanism in the ordered manner.This study offers alternative perspectives on the dissolution and stability mechanism of RuO_(2) and the facet-selective modulation of nanocrystals by ligand-driven etching.
