A variety of 3-nitroindazoles and 3-aminoindazoles were prepared in good to excellent yields with high regioselectivity through TBN-mediated nitration at the C3-position of indazoles under the air conditions and seque...A variety of 3-nitroindazoles and 3-aminoindazoles were prepared in good to excellent yields with high regioselectivity through TBN-mediated nitration at the C3-position of indazoles under the air conditions and sequential reduction.Mechanistic studies revealed that TBN played crucial roles to produce·NO_(2) radical source in the presence of air conditions and C3-nitration of indazoles was initiated by N1-nitration and sequential migration of NO_(2) group to C3-position.Moreover,this method could be easily applied in the gram scalable synthesis of ibuprofen and ciprofibrate-derived 3-aminoindazoles.The present method highlights air as mild oxidant,metal-free radical nitration of indazole,N—N bond formation and cleavage,and late-stage modification of drugs.展开更多
A catalyst-,acid-and base-free,environmental-friendly method for synthesis of 2/7-benzo[g]furo[2,3-e]indazoles,2H-benzo[g]-thieno[2,3-e]indazoles and 2H-benzo[g]pyrrolo[2,3-e]indazoles via UV light irradiation of 3-ph...A catalyst-,acid-and base-free,environmental-friendly method for synthesis of 2/7-benzo[g]furo[2,3-e]indazoles,2H-benzo[g]-thieno[2,3-e]indazoles and 2H-benzo[g]pyrrolo[2,3-e]indazoles via UV light irradiation of 3-phenyl-4-(2-heteroaryl)pyrazoles(aryl=furanyl,thiophenyl and N-methylpyrrolyl)in EtOH/H_(2)O at room temperature under argon atmosphere was described.展开更多
A novel difluorocarbene promoted single-atom skeletal editing of 2H-indazoles is demonstrated herein.Ethyl bromodifluoroacetate was severed as the difluorocarbene source in the current protocol,facilitating the cleava...A novel difluorocarbene promoted single-atom skeletal editing of 2H-indazoles is demonstrated herein.Ethyl bromodifluoroacetate was severed as the difluorocarbene source in the current protocol,facilitating the cleavage of the N-N bond via carbon atom insertion.This metal-free ring expansion reaction enables the late-stage diversification of indazole skeletons,assembling a diverse array of functionalized quinazolin-4(3H)-ones in decent yields with excellent functional group compatibility.展开更多
近日,药学领域权威期刊《Acta Pharmaceutica Sinica B》(IF=14.8)在线发表了沈阳药科大学制药工程学院胡春教授课题组和香港中文大学邵鹏柱教授课题组在抗流感药物研究领域的最新成果,文章题目为“Design, synthesis and biological ev...近日,药学领域权威期刊《Acta Pharmaceutica Sinica B》(IF=14.8)在线发表了沈阳药科大学制药工程学院胡春教授课题组和香港中文大学邵鹏柱教授课题组在抗流感药物研究领域的最新成果,文章题目为“Design, synthesis and biological evaluation of a novel class of indazole-containing compounds with potent anti-influenza activities targeting the PA-PB1 interface”。展开更多
The title compound 1-(3-amino-4-morpholino-1H-indazole-1-carbonyl)-N-(4-fluorophenyl)cyclopropane-1-carboxamide was synthesized by the condensation of 1-[(4-fluorophenyl)carbamoyl]cyclopropane-1-carboxylic acid with 4...The title compound 1-(3-amino-4-morpholino-1H-indazole-1-carbonyl)-N-(4-fluorophenyl)cyclopropane-1-carboxamide was synthesized by the condensation of 1-[(4-fluorophenyl)carbamoyl]cyclopropane-1-carboxylic acid with 4-morpholino-1H-indazol-3-amine.This intermediate was prepared from 2,6-difluorobenzonitrile by the condensation with morpholine and then cyclisation with hydrazine hydrate.The crystal structure of the title compound was determined to be of monoclinic system,space group P21/c with a=10.4645(13),b=17.368(2),c=13.7220(13)? and β=21.446(7)°.In addition,the compound possesses distinct effective inhibition on the proliferation of HT-29,MKN-45,K562 and A549 cell lines.展开更多
A new silver complex salt [Ag(N2C11H10)2]NO3 (where N2C11H10 = 4,5-dihydro-1H-benzo[g]indazole), has been synthesized and characterized by elemental and thermal analyses, IR and 1HNMR spectroscopies, single crystal X-...A new silver complex salt [Ag(N2C11H10)2]NO3 (where N2C11H10 = 4,5-dihydro-1H-benzo[g]indazole), has been synthesized and characterized by elemental and thermal analyses, IR and 1HNMR spectroscopies, single crystal X-ray structure determination and DFT studies. Its molecular structure comprises of a silver center coordinated to two nitrogen atoms from two 4,5-dihydro-1H-benzo[g]indazole molecule giving rise to a cationic complex entity, [Ag(N2C11H10)2]+ with as counter ion. The bulk structure is consolidated by N–H…O, C–H…π, Ag…π and Ag…O intermolecular interactions, thus generating a pseudo-helical network. The optimized structure, frontier molecular orbitals (HOMO and LUMO) and global reactivity descriptors were investigated by performing DFT calculations.展开更多
A series of novel amide derivatives bearing an indazole moiety were synthesized and evaluated for their in vitro S-adenosylL-homocysteine hydrolase（SAHase） inhibitory activity. Among these compounds, 8b,8m, 8r and 8...A series of novel amide derivatives bearing an indazole moiety were synthesized and evaluated for their in vitro S-adenosylL-homocysteine hydrolase（SAHase） inhibitory activity. Among these compounds, 8b,8m, 8r and 8w showed better or similar inhibitory effects compared to the positive control aristeromycin. These results provide a novel lead for the discovery of more potent non-adenosine analogs as SAHase inhibitors.展开更多
The new salt bis(4,5-dihydro-1H-benzo[g]indazole)silver(I) hexafluorophosphate, [Ag(N2H10C11)2]PF6, has been synthesized in methanol at ambient temperature and characterized by elemental and thermal analyses, FTIR and...The new salt bis(4,5-dihydro-1H-benzo[g]indazole)silver(I) hexafluorophosphate, [Ag(N2H10C11)2]PF6, has been synthesized in methanol at ambient temperature and characterized by elemental and thermal analyses, FTIR and 1HNMR spectroscopies, Rietveld refinement from powder diffraction data and DFT studies. The salt crystallizes in the triclinic space group P-1 with the parameters: a = 7.776 ?, b = 8.676 ?, c = 9.226 ?, α = 69.27° β = 89.86°, γ = 74.50°, V = 558.02 ?3, Z = 1. In the structure, the silver center is coordinated to two nitrogen atoms from two 4,5-dihydro-1H-benzo[g]indazole ligands, forming a centrosymmetric complex cation, [Ag(N2H10C11)2]+, with a linear coordination geometry around the silver center. The hexafluorophosphate ion, , acts as counter anion. The crystal packing is governed by N-H···F and C-H···F hydrogen bonds that interconnect the ionic constituents and Ag···F and Ag···π interactions help for the stabilization of the packing. The optimized structure was obtained at B3LYP/LanL2DZ level in the gas phase. The stability and reactivity of the structure were studied using respectively HOMO-LUMO gap and electronic global quantities (ionization potential (I) and electron affinity (A)) as descriptors.展开更多
A novel method for the asymmetric synthesis of 1,7-annulated indazoles has been developed via bifunctional Brønsted base catalyzed cascade reaction.This process enabled the formation of multiple chiral centers in...A novel method for the asymmetric synthesis of 1,7-annulated indazoles has been developed via bifunctional Brønsted base catalyzed cascade reaction.This process enabled the formation of multiple chiral centers including a quaternary carbon center in high yields with excellent diastereoselectivities and enantioselectivities.The reaction exhibited broad functional group tolerance and mild reaction conditions.展开更多
基金the NSFC(22071035)Natural Science Foundation of Guangxi(2023GXNSFDA026025)Guangxi Bagui Young Scholar is greatly appreciated.
文摘A variety of 3-nitroindazoles and 3-aminoindazoles were prepared in good to excellent yields with high regioselectivity through TBN-mediated nitration at the C3-position of indazoles under the air conditions and sequential reduction.Mechanistic studies revealed that TBN played crucial roles to produce·NO_(2) radical source in the presence of air conditions and C3-nitration of indazoles was initiated by N1-nitration and sequential migration of NO_(2) group to C3-position.Moreover,this method could be easily applied in the gram scalable synthesis of ibuprofen and ciprofibrate-derived 3-aminoindazoles.The present method highlights air as mild oxidant,metal-free radical nitration of indazole,N—N bond formation and cleavage,and late-stage modification of drugs.
基金We are grateful for financial support by the National Natural Science Foundation of China(No.21672132).
文摘A catalyst-,acid-and base-free,environmental-friendly method for synthesis of 2/7-benzo[g]furo[2,3-e]indazoles,2H-benzo[g]-thieno[2,3-e]indazoles and 2H-benzo[g]pyrrolo[2,3-e]indazoles via UV light irradiation of 3-phenyl-4-(2-heteroaryl)pyrazoles(aryl=furanyl,thiophenyl and N-methylpyrrolyl)in EtOH/H_(2)O at room temperature under argon atmosphere was described.
基金supported by the National Natural Science Foundation of China(21931013,22271105)the Natural Science Foundation of Fujian Province(2022J02009)+1 种基金the Science and Technology Research Project of Education Department of Hubei Province(B2021133)the Hubei Key Laboratory of Pollutant Analysis&Reuse Technology(PA190109)
文摘A novel difluorocarbene promoted single-atom skeletal editing of 2H-indazoles is demonstrated herein.Ethyl bromodifluoroacetate was severed as the difluorocarbene source in the current protocol,facilitating the cleavage of the N-N bond via carbon atom insertion.This metal-free ring expansion reaction enables the late-stage diversification of indazole skeletons,assembling a diverse array of functionalized quinazolin-4(3H)-ones in decent yields with excellent functional group compatibility.
文摘近日,药学领域权威期刊《Acta Pharmaceutica Sinica B》(IF=14.8)在线发表了沈阳药科大学制药工程学院胡春教授课题组和香港中文大学邵鹏柱教授课题组在抗流感药物研究领域的最新成果,文章题目为“Design, synthesis and biological evaluation of a novel class of indazole-containing compounds with potent anti-influenza activities targeting the PA-PB1 interface”。
基金Supported by the Team of Syngas Catalytic Conversion of Shaanxi University of Technologythe Youth National Natural Science Foundation of China(No.21373132,21603133)+2 种基金the key project of education department of Shaanxi province(18JS023)the Project of Shaanxi Provincial Science and Technology Department(2019JQ149,2019JM471)the project of Shaanxi University of technology(SLGQD2017-14)
文摘The title compound 1-(3-amino-4-morpholino-1H-indazole-1-carbonyl)-N-(4-fluorophenyl)cyclopropane-1-carboxamide was synthesized by the condensation of 1-[(4-fluorophenyl)carbamoyl]cyclopropane-1-carboxylic acid with 4-morpholino-1H-indazol-3-amine.This intermediate was prepared from 2,6-difluorobenzonitrile by the condensation with morpholine and then cyclisation with hydrazine hydrate.The crystal structure of the title compound was determined to be of monoclinic system,space group P21/c with a=10.4645(13),b=17.368(2),c=13.7220(13)? and β=21.446(7)°.In addition,the compound possesses distinct effective inhibition on the proliferation of HT-29,MKN-45,K562 and A549 cell lines.
文摘A new silver complex salt [Ag(N2C11H10)2]NO3 (where N2C11H10 = 4,5-dihydro-1H-benzo[g]indazole), has been synthesized and characterized by elemental and thermal analyses, IR and 1HNMR spectroscopies, single crystal X-ray structure determination and DFT studies. Its molecular structure comprises of a silver center coordinated to two nitrogen atoms from two 4,5-dihydro-1H-benzo[g]indazole molecule giving rise to a cationic complex entity, [Ag(N2C11H10)2]+ with as counter ion. The bulk structure is consolidated by N–H…O, C–H…π, Ag…π and Ag…O intermolecular interactions, thus generating a pseudo-helical network. The optimized structure, frontier molecular orbitals (HOMO and LUMO) and global reactivity descriptors were investigated by performing DFT calculations.
基金supported by National Natural Science Foundation of China (No. 81560653)Guangxi Natural Science Foundation of China (No. 2015GXNSFBA139124)
文摘A series of novel amide derivatives bearing an indazole moiety were synthesized and evaluated for their in vitro S-adenosylL-homocysteine hydrolase（SAHase） inhibitory activity. Among these compounds, 8b,8m, 8r and 8w showed better or similar inhibitory effects compared to the positive control aristeromycin. These results provide a novel lead for the discovery of more potent non-adenosine analogs as SAHase inhibitors.
文摘The new salt bis(4,5-dihydro-1H-benzo[g]indazole)silver(I) hexafluorophosphate, [Ag(N2H10C11)2]PF6, has been synthesized in methanol at ambient temperature and characterized by elemental and thermal analyses, FTIR and 1HNMR spectroscopies, Rietveld refinement from powder diffraction data and DFT studies. The salt crystallizes in the triclinic space group P-1 with the parameters: a = 7.776 ?, b = 8.676 ?, c = 9.226 ?, α = 69.27° β = 89.86°, γ = 74.50°, V = 558.02 ?3, Z = 1. In the structure, the silver center is coordinated to two nitrogen atoms from two 4,5-dihydro-1H-benzo[g]indazole ligands, forming a centrosymmetric complex cation, [Ag(N2H10C11)2]+, with a linear coordination geometry around the silver center. The hexafluorophosphate ion, , acts as counter anion. The crystal packing is governed by N-H···F and C-H···F hydrogen bonds that interconnect the ionic constituents and Ag···F and Ag···π interactions help for the stabilization of the packing. The optimized structure was obtained at B3LYP/LanL2DZ level in the gas phase. The stability and reactivity of the structure were studied using respectively HOMO-LUMO gap and electronic global quantities (ionization potential (I) and electron affinity (A)) as descriptors.
基金the Qingdao Marine Science and Technology Center(No.2022QNLM030003-2)the Fundamental Research Funds for the Central Universities,Taishan Scholar Program of Shandong Province(No.tsqn201909056)+1 种基金Natural Science Foundation of Shandong Province(No.ZR2024MB122)National Natural Science Foundation of China(No.22171251)for financial support.
文摘A novel method for the asymmetric synthesis of 1,7-annulated indazoles has been developed via bifunctional Brønsted base catalyzed cascade reaction.This process enabled the formation of multiple chiral centers including a quaternary carbon center in high yields with excellent diastereoselectivities and enantioselectivities.The reaction exhibited broad functional group tolerance and mild reaction conditions.
