A series of imidazo[1,2-a]pyrimidine derivatives substituted adjacently with two aryls at positions 2 and 3 were designed and synthesized in order to improve their anti-inflammatory activities. Biological tests sugges...A series of imidazo[1,2-a]pyrimidine derivatives substituted adjacently with two aryls at positions 2 and 3 were designed and synthesized in order to improve their anti-inflammatory activities. Biological tests suggested that these compounds have antiinflammatory activities with COX-2 selectivity to some extent.展开更多
Room temperature ionic liquids were used as a "green" recyclable alternative to conventional solvents in the synthesis of pharmaceutically useful compounds 2-arylimidazo[1, 2-a] pyrimidines through Tschotsch...Room temperature ionic liquids were used as a "green" recyclable alternative to conventional solvents in the synthesis of pharmaceutically useful compounds 2-arylimidazo[1, 2-a] pyrimidines through Tschotschibabin reaction of a-bromoacetophenones with 2-aminopyrimidine in good yields.展开更多
Benzo[4,5]imidazo[1,2-a]pyrimidine-based derivatives play crucial roles in medicines,pesticides,tracers and photoelectric materials.However,their synthesis approach still needs to be optimized,and their fluorescent pr...Benzo[4,5]imidazo[1,2-a]pyrimidine-based derivatives play crucial roles in medicines,pesticides,tracers and photoelectric materials.However,their synthesis approach still needs to be optimized,and their fluorescent properties in intracellular microenvironment are unclear.Here,a Cu(II)-catalyzed cascade coupling cyclization reaction was successfully developed to synthesize benzo[4,5]imidazo[1,2-a]pyrimidine scaffold with mild reaction conditions,broad substrate scopes and high yields.After a system study,we found that compound 4aa displayed an optimal viscosity-specific response with remarkable fluorescence enhancement(102-fold)for glycerol at 490 nm.Particularly,4aa possessed excellent structure-inherent targeting(SIT)capability for lysosome(P=0.95)with high p H stability and large Stokes shift.Importantly,4aa was validated for its effectiveness in diagnosing lysosomal storage disorders(LSD)in living cells.The 4aa also showed its potential to map the micro-viscosity and its metabolism process in zebrafish.This work not only affords an efficient protocol to fabricate benzo[4,5]imidazo[1,2-a]pyrimidine derivatives,reveals this skeleton has excellent SIT features for lysosome,but also manifests that 4aa can serve as a practical tool to monitor lysosomal viscosity and diagnose LSD.展开更多
The synthesis of new 4-imino-4H-chromeno[2,3-d]pyrimidin-3(5H)-amine in four steps including one step under microwave dielectric heating is reported. The structural identity of the synthesized compounds was establishe...The synthesis of new 4-imino-4H-chromeno[2,3-d]pyrimidin-3(5H)-amine in four steps including one step under microwave dielectric heating is reported. The structural identity of the synthesized compounds was established according to their spectroscopic analysis, such as FT-IR, NMR and mass spectroscopy. These new compounds were tested for their antiproliferative activities on seven representative human tumoral cell lines (Huh7 D12, Caco2, MDA-MB231, MDA-MB468, HCT116, PC3 and MCF7) and also on fibroblasts. Among them, only the compounds 6c showed micromolar cytotoxic activity on tumor cell lines (1.8 50 50 > 25 μM). Finally, in silico ADMET studies ware performed to investigate the possibility of using of the identified compound 6c as potential anti-tumor compound.展开更多
A new synthetic strategy for the synthesis of novel 3-（3-（3-methyl-4-nitroisoxazol-5-yl）-2-phenyl-1-（5,7-diaryl-7H-thia- zolo[3,2-a]pyrimidin-3-yl）propyl）-5,7-diaryl-7H-thiazolo[3,2-a]pyrimidines （7a-i） analog...A new synthetic strategy for the synthesis of novel 3-（3-（3-methyl-4-nitroisoxazol-5-yl）-2-phenyl-1-（5,7-diaryl-7H-thia- zolo[3,2-a]pyrimidin-3-yl）propyl）-5,7-diaryl-7H-thiazolo[3,2-a]pyrimidines （7a-i） analogues is described. Reaction of 3-（2- （3-methyl-4-nitroisoxazole-5-yl）-l-phenylethyl）pentane-2,4-dione （3） with two moles of thiourea in presence of iodine and CuO afforded 4-（1-（2-aminothiazol-4-yl）-3-（3-methyl-4-nitroisoxazol-5-yl）-2-aryl propylthiazol-2-amine （5）. Compound 5 on reaction with two moles of chalcone （6） furnished novel 3-（3-（3-methyl-4-nitroisoxazol-5-yl）-2-phenyl-1-（5,7-diaryl-7H-thiazolo[3,2- a]pyrimidin-3-yl）propyl）-5,7-diaryl-7H-thiazolo[3,2-a ]pyrimidines （Ta-i）.展开更多
基金This research was supported by the National Natural Science Foundation of China （No.30472083）.
文摘A series of imidazo[1,2-a]pyrimidine derivatives substituted adjacently with two aryls at positions 2 and 3 were designed and synthesized in order to improve their anti-inflammatory activities. Biological tests suggested that these compounds have antiinflammatory activities with COX-2 selectivity to some extent.
文摘Room temperature ionic liquids were used as a "green" recyclable alternative to conventional solvents in the synthesis of pharmaceutically useful compounds 2-arylimidazo[1, 2-a] pyrimidines through Tschotschibabin reaction of a-bromoacetophenones with 2-aminopyrimidine in good yields.
基金supported by the National Natural Science Foundation of China(Nos.22077099,22171223 and 22307102)the Innovation Capability Support Program of Shaanxi(Nos.2023-CXTD-75 and 2022KJXX-32)+5 种基金the Technology Innovation Leading Program of Shaanxi(Nos.2023KXJ-209 and 2024QCY-KXJ-142)the Key Research and Development Program of Shaanxi(No.2024GHZDXM-22)the Natural Science Basic Research Program of Shaanxi(Nos.2023-JC-YB-141 and 2022JQ-151)Young Talent Fund of Association for Science and Technology in Shaanxi,China(No.SWYY202206)the Shaanxi Fundamental Science Research Project for Chemistry&Biology(Nos.22JHZ010 and 22JHQ080)the Yan’an City Science and Technology Project(No.2022SLZDCY-002)。
文摘Benzo[4,5]imidazo[1,2-a]pyrimidine-based derivatives play crucial roles in medicines,pesticides,tracers and photoelectric materials.However,their synthesis approach still needs to be optimized,and their fluorescent properties in intracellular microenvironment are unclear.Here,a Cu(II)-catalyzed cascade coupling cyclization reaction was successfully developed to synthesize benzo[4,5]imidazo[1,2-a]pyrimidine scaffold with mild reaction conditions,broad substrate scopes and high yields.After a system study,we found that compound 4aa displayed an optimal viscosity-specific response with remarkable fluorescence enhancement(102-fold)for glycerol at 490 nm.Particularly,4aa possessed excellent structure-inherent targeting(SIT)capability for lysosome(P=0.95)with high p H stability and large Stokes shift.Importantly,4aa was validated for its effectiveness in diagnosing lysosomal storage disorders(LSD)in living cells.The 4aa also showed its potential to map the micro-viscosity and its metabolism process in zebrafish.This work not only affords an efficient protocol to fabricate benzo[4,5]imidazo[1,2-a]pyrimidine derivatives,reveals this skeleton has excellent SIT features for lysosome,but also manifests that 4aa can serve as a practical tool to monitor lysosomal viscosity and diagnose LSD.
文摘The synthesis of new 4-imino-4H-chromeno[2,3-d]pyrimidin-3(5H)-amine in four steps including one step under microwave dielectric heating is reported. The structural identity of the synthesized compounds was established according to their spectroscopic analysis, such as FT-IR, NMR and mass spectroscopy. These new compounds were tested for their antiproliferative activities on seven representative human tumoral cell lines (Huh7 D12, Caco2, MDA-MB231, MDA-MB468, HCT116, PC3 and MCF7) and also on fibroblasts. Among them, only the compounds 6c showed micromolar cytotoxic activity on tumor cell lines (1.8 50 50 > 25 μM). Finally, in silico ADMET studies ware performed to investigate the possibility of using of the identified compound 6c as potential anti-tumor compound.
文摘A new synthetic strategy for the synthesis of novel 3-（3-（3-methyl-4-nitroisoxazol-5-yl）-2-phenyl-1-（5,7-diaryl-7H-thia- zolo[3,2-a]pyrimidin-3-yl）propyl）-5,7-diaryl-7H-thiazolo[3,2-a]pyrimidines （7a-i） analogues is described. Reaction of 3-（2- （3-methyl-4-nitroisoxazole-5-yl）-l-phenylethyl）pentane-2,4-dione （3） with two moles of thiourea in presence of iodine and CuO afforded 4-（1-（2-aminothiazol-4-yl）-3-（3-methyl-4-nitroisoxazol-5-yl）-2-aryl propylthiazol-2-amine （5）. Compound 5 on reaction with two moles of chalcone （6） furnished novel 3-（3-（3-methyl-4-nitroisoxazol-5-yl）-2-phenyl-1-（5,7-diaryl-7H-thiazolo[3,2- a]pyrimidin-3-yl）propyl）-5,7-diaryl-7H-thiazolo[3,2-a ]pyrimidines （Ta-i）.
