The magnetic nanoparticles supported silica sulfuric acid was used as an efficient catalyst for the synthesis of pyrimido[4,5-b]quinoIines and indeno fused pyrido（2,3-d]pyrimidines in water.The desired products were ...The magnetic nanoparticles supported silica sulfuric acid was used as an efficient catalyst for the synthesis of pyrimido[4,5-b]quinoIines and indeno fused pyrido（2,3-d]pyrimidines in water.The desired products were obtained in excellent yields.Fe_3O_4@SiO_2-SO_3H was readily recovered using an external magnet and could be reused several times without significant loss of reactivity.展开更多
A reaction between 1,3-dioxo-N-aryl-2,3-dihydro-lH-indene-2-carboxamides, dialkyl acetylenedicar- boxylates, and triphenylphosphine or trimethylphosphite is described as a simple and efficient method for the synthesis...A reaction between 1,3-dioxo-N-aryl-2,3-dihydro-lH-indene-2-carboxamides, dialkyl acetylenedicar- boxylates, and triphenylphosphine or trimethylphosphite is described as a simple and efficient method for the synthesis of 5-hydroxy-4-aryl-2,5-dihydrofuran-2,3-dicarboxylate derivatives.展开更多
The present work describes a facile, one-pot three component environment friendly, green synthesis of a series of 5-（4-methoxyphenyl）-7,7-dimethyl-10-phenyl-7,8-dihydro-SH-indeno[ 1,2-b]quinoline- 9,11 （6H,10H）-di...The present work describes a facile, one-pot three component environment friendly, green synthesis of a series of 5-（4-methoxyphenyl）-7,7-dimethyl-10-phenyl-7,8-dihydro-SH-indeno[ 1,2-b]quinoline- 9,11 （6H,10H）-dione derivatives 8（a-n）. 1,3-indanedione, awl-aldehyde and enaminone was thoroughly ground in the presence of catalytic amount of p-toluene sulfonic acid （p-TSA） to give the titled compounds in good yields. All the synthesized derivatives were evaluated for their anticonvulsant activity using the maximal electroshock （MES） method with phenytoin as a standard drug along with their neurotoxicity effect. Derivatives 8b, 8e and 8k exhibited significant anticonvulsant activity （P 〈 0.001）. The neurotoxicity study clearly revealed that all the tested compounds are non-toxic at a dose of 40 mg/kg. The molecular modeling studies also predicted good binding interactions of most active molecules with the serotonin 5-HT2A receptor. Therefore, it can be safely concluded that synthesized derivatives 8（a-n） would represent useful leads for further investigation in the development of a new class of anticonvulsant agents.展开更多
A single compound able to inhibit both TopoⅠandⅡmay present the advantage of improving anti-proliferative activity,with reduced toxic side effects,with respect to the combination of two inhibitors.We designed and sy...A single compound able to inhibit both TopoⅠandⅡmay present the advantage of improving anti-proliferative activity,with reduced toxic side effects,with respect to the combination of two inhibitors.We designed and synthesized 28 compounds of indeno[1,2-b]indole derivatives as a new class of TopoⅠandⅡinhibitor and successfully identified compound 2-3 j,which showed the most potent cell growth inhibition with IC50=0.74μM against HCT-116 cell line.Compound 2-3 j was also evaluated as a potent topoisomeraseⅠandⅡinhibitor and can induce apoptosis in human colon cancer cells.2-3 j showed potency against a small panel of drug sensitive and multidrug resistant(MDR)cell lines,and it reversed the MDR of K562/A02,MCF-7/Adr,and KB/Vcr cells at 0.5μM,with reversal fold values of 3.2,10.1,and 5.8,respectively.2-3 j might inhibit the function of ABCG2 to increase intracellular drug accumulation and enhance the sensitivity of conventional chemotherapeutic agents for MDR cells.2-3 j could be a promising lead for the development of a new class of antitumor drug acting as inhibitors of TopoⅠ&Ⅱand ABCG2.展开更多
Hexakis(4-methoxyphenyl)benzene (HPB-OMe(1)) and hexakis(2,6-dimethyl-4-methoxyphenyl)benzene (HPB-OMe(2)) were synthesized via organometallic complex catalysis. The treatment of HPB-OMe(1) with FeCl3 caused cyclodehy...Hexakis(4-methoxyphenyl)benzene (HPB-OMe(1)) and hexakis(2,6-dimethyl-4-methoxyphenyl)benzene (HPB-OMe(2)) were synthesized via organometallic complex catalysis. The treatment of HPB-OMe(1) with FeCl3 caused cyclodehydrogenation at two positions to yield an oligophenylene with an indeno[1,2-b]fluorene structure (IF-OMe). Deprotection of the methoxy groups of these compounds was conducted by treatment with BBr3. Deprotonation of the OH groups of HPB-OH(1), HPB-OH(2), and IF-OH through treatment with NaH caused a bathochromic shift in the absorption and photoluminescence (PL) peaks. The bathochromic shift of the deprotonated species increased with the donor number (DN) of the solvents. These observations can be explained as the consequence of intramolecular charge transfer (ICT) from the ONa groups to the inner benzene rings.展开更多
The nine new 11H-indeno[1,2-b]quinolines were synthesized in high yield with sodium ethoxide as a catalyst via the Friedlander condensation reaction, The possible reaction mechanism was proposed.
The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by densit...The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by density functional theory. The geometries of the reactants, transition states, intermediates and products were optimized at the PW91/DNP level. Vibration analysis was carried out to confirm the transition state structure. Reaction pathways were investigated in this study. The result indicates that the reaction Re→ TSB1→IMB1→ TSB2→ IMB2→TSB3→IMB3→TSB4→IMB4→TSB5→IMB5→TSB6→IMB6→TSB7→IMB7→ TSB8→IMB8→TSB9→IMB9→P2 is the main pathway, the activation energy of which is the lowest. The dominant product predicted theoretically is in agreement with the experiment results.展开更多
基金the Department of Chemistry and the office of gifted students at Semnan University for their financial support
文摘The magnetic nanoparticles supported silica sulfuric acid was used as an efficient catalyst for the synthesis of pyrimido[4,5-b]quinoIines and indeno fused pyrido（2,3-d]pyrimidines in water.The desired products were obtained in excellent yields.Fe_3O_4@SiO_2-SO_3H was readily recovered using an external magnet and could be reused several times without significant loss of reactivity.
文摘A reaction between 1,3-dioxo-N-aryl-2,3-dihydro-lH-indene-2-carboxamides, dialkyl acetylenedicar- boxylates, and triphenylphosphine or trimethylphosphite is described as a simple and efficient method for the synthesis of 5-hydroxy-4-aryl-2,5-dihydrofuran-2,3-dicarboxylate derivatives.
文摘The present work describes a facile, one-pot three component environment friendly, green synthesis of a series of 5-（4-methoxyphenyl）-7,7-dimethyl-10-phenyl-7,8-dihydro-SH-indeno[ 1,2-b]quinoline- 9,11 （6H,10H）-dione derivatives 8（a-n）. 1,3-indanedione, awl-aldehyde and enaminone was thoroughly ground in the presence of catalytic amount of p-toluene sulfonic acid （p-TSA） to give the titled compounds in good yields. All the synthesized derivatives were evaluated for their anticonvulsant activity using the maximal electroshock （MES） method with phenytoin as a standard drug along with their neurotoxicity effect. Derivatives 8b, 8e and 8k exhibited significant anticonvulsant activity （P 〈 0.001）. The neurotoxicity study clearly revealed that all the tested compounds are non-toxic at a dose of 40 mg/kg. The molecular modeling studies also predicted good binding interactions of most active molecules with the serotonin 5-HT2A receptor. Therefore, it can be safely concluded that synthesized derivatives 8（a-n） would represent useful leads for further investigation in the development of a new class of anticonvulsant agents.
基金The National Natural Science Foundation of China(Grant No.81573272,81273370)Changjiang Scholars and Innovative Research Team in University(Grant No.IRT13028)
文摘A single compound able to inhibit both TopoⅠandⅡmay present the advantage of improving anti-proliferative activity,with reduced toxic side effects,with respect to the combination of two inhibitors.We designed and synthesized 28 compounds of indeno[1,2-b]indole derivatives as a new class of TopoⅠandⅡinhibitor and successfully identified compound 2-3 j,which showed the most potent cell growth inhibition with IC50=0.74μM against HCT-116 cell line.Compound 2-3 j was also evaluated as a potent topoisomeraseⅠandⅡinhibitor and can induce apoptosis in human colon cancer cells.2-3 j showed potency against a small panel of drug sensitive and multidrug resistant(MDR)cell lines,and it reversed the MDR of K562/A02,MCF-7/Adr,and KB/Vcr cells at 0.5μM,with reversal fold values of 3.2,10.1,and 5.8,respectively.2-3 j might inhibit the function of ABCG2 to increase intracellular drug accumulation and enhance the sensitivity of conventional chemotherapeutic agents for MDR cells.2-3 j could be a promising lead for the development of a new class of antitumor drug acting as inhibitors of TopoⅠ&Ⅱand ABCG2.
文摘Hexakis(4-methoxyphenyl)benzene (HPB-OMe(1)) and hexakis(2,6-dimethyl-4-methoxyphenyl)benzene (HPB-OMe(2)) were synthesized via organometallic complex catalysis. The treatment of HPB-OMe(1) with FeCl3 caused cyclodehydrogenation at two positions to yield an oligophenylene with an indeno[1,2-b]fluorene structure (IF-OMe). Deprotection of the methoxy groups of these compounds was conducted by treatment with BBr3. Deprotonation of the OH groups of HPB-OH(1), HPB-OH(2), and IF-OH through treatment with NaH caused a bathochromic shift in the absorption and photoluminescence (PL) peaks. The bathochromic shift of the deprotonated species increased with the donor number (DN) of the solvents. These observations can be explained as the consequence of intramolecular charge transfer (ICT) from the ONa groups to the inner benzene rings.
基金the Natural Science Foundation of Guangdong Province for the financial support （No. 04010404）.
文摘The nine new 11H-indeno[1,2-b]quinolines were synthesized in high yield with sodium ethoxide as a catalyst via the Friedlander condensation reaction, The possible reaction mechanism was proposed.
基金Project supported by the Scientific and Technological Research Program of Chongqing Municipal Education Commission(KJ1601215,KJ15012002)the Ministry of Education “Chunhui Plan”(Z2016177)
文摘The reaction mechanism of 2-methoxybenzaldehyde, 4-bromo-indanone, malononitrile and ammonium acetate one-pot to form 6-（2-methoxyphenyl）-2-amino-6-bromo-5 Hindeno[1,2-b]pyridine-3-carbonitrile was studied by density functional theory. The geometries of the reactants, transition states, intermediates and products were optimized at the PW91/DNP level. Vibration analysis was carried out to confirm the transition state structure. Reaction pathways were investigated in this study. The result indicates that the reaction Re→ TSB1→IMB1→ TSB2→ IMB2→TSB3→IMB3→TSB4→IMB4→TSB5→IMB5→TSB6→IMB6→TSB7→IMB7→ TSB8→IMB8→TSB9→IMB9→P2 is the main pathway, the activation energy of which is the lowest. The dominant product predicted theoretically is in agreement with the experiment results.
