目的合成一系列新型结构6-芳基茚并异喹啉酮衍生物,并考察目标化合物对DNA拓扑异构酶Ⅰ(TopoⅠ)的抑制活性及其体外抗肿瘤活性。方法以茚和间氯苯甲酸为原料,分别合成高酞酸和4-甲氧基高酞酸;高酞酸通过脱水反应、与亚胺加成反应制得中...目的合成一系列新型结构6-芳基茚并异喹啉酮衍生物,并考察目标化合物对DNA拓扑异构酶Ⅰ(TopoⅠ)的抑制活性及其体外抗肿瘤活性。方法以茚和间氯苯甲酸为原料,分别合成高酞酸和4-甲氧基高酞酸;高酞酸通过脱水反应、与亚胺加成反应制得中间体6-芳基茚并异喹啉酮;该中间体与各种氨基取代的氯代物反应得到目标化合物。采用TopoGEN公司的Topoisomerase Ⅰ drug screning kit来测试目标化合物对TopoⅠ的抑制活性;选取人乳腺癌细胞(MCF-7)、非小细胞肺癌细胞(NIH-H460)和人神经胶质瘤细胞(U251)对目标化合物进行体外抗肿瘤活性筛选。结果与结论共合成了17个未见文献报道的新化合物,其结构均经MS(EI)、1H-NMR确证。体外活性筛选结果表明:目标化合物对TopoⅠ表现出良好的抑制作用,且对3种肿瘤细胞表现出较好的抗增殖活性。展开更多
An efficient visible-light-induced radical cascade azidation/cyclization of 2-aryl indoles with trimethylsilyl azide(TMSN3)has been developed using organic dye Rose Bengal as the photocatalyst.This method did not requ...An efficient visible-light-induced radical cascade azidation/cyclization of 2-aryl indoles with trimethylsilyl azide(TMSN3)has been developed using organic dye Rose Bengal as the photocatalyst.This method did not require metal catalysts and additives,and used air as the oxidant to obtain diverse indolo[2,1-a]isoquinolin-6(5H)-ones in moderate to good yields.Mechanistic studies demonstrated that the reaction proceeded via a radical pathway.展开更多
Employing triflic anhydride/2-fluoropyridine as an activation system, the coupling reactions of secondary N-aryl amides with terminal alkynes yielded substituted quinolines in moderate to excellent yields. The reactio...Employing triflic anhydride/2-fluoropyridine as an activation system, the coupling reactions of secondary N-aryl amides with terminal alkynes yielded substituted quinolines in moderate to excellent yields. The reaction tolerated both electron-donating and electron-withdrawing groups at the benzamide moiety. Electron-rich aryl acetylenes served as excellent coupling partners, and aliphatic terminal alkynes such as cyclopropyl and conjugate vinyl acetylenes could also be used as reaction partners. By means of 2 D NMR techniques(heteronuclear multiple bond correlation(HMBC), heteronuclear single quantum correlation(HSQC)),nitrilium ions were probed as reactive intermediates which are in contrast with that suggested by Movassaghi on the basis of in situ IR monitoring experiments. On the basis of these results, a plausible mechanism for the formation of quinolines was suggested.展开更多
Efforts toward the total synthesis of indolactam V via CuI-mediated inter- and intra-molecular N-arylation of 4-iodotryptophan derivatives for the introduction of 4-valine moiety from natural L-valine are described. M...Efforts toward the total synthesis of indolactam V via CuI-mediated inter- and intra-molecular N-arylation of 4-iodotryptophan derivatives for the introduction of 4-valine moiety from natural L-valine are described. Meanwhile, the efficient synthesis of several pyrroloquinoline derivatives by taking advantage of the CuI-catalyzed intramolecular N-arylation reaction of 4-iodotryptophan is disclosed.展开更多
文摘目的合成一系列新型结构6-芳基茚并异喹啉酮衍生物,并考察目标化合物对DNA拓扑异构酶Ⅰ(TopoⅠ)的抑制活性及其体外抗肿瘤活性。方法以茚和间氯苯甲酸为原料,分别合成高酞酸和4-甲氧基高酞酸;高酞酸通过脱水反应、与亚胺加成反应制得中间体6-芳基茚并异喹啉酮;该中间体与各种氨基取代的氯代物反应得到目标化合物。采用TopoGEN公司的Topoisomerase Ⅰ drug screning kit来测试目标化合物对TopoⅠ的抑制活性;选取人乳腺癌细胞(MCF-7)、非小细胞肺癌细胞(NIH-H460)和人神经胶质瘤细胞(U251)对目标化合物进行体外抗肿瘤活性筛选。结果与结论共合成了17个未见文献报道的新化合物,其结构均经MS(EI)、1H-NMR确证。体外活性筛选结果表明:目标化合物对TopoⅠ表现出良好的抑制作用,且对3种肿瘤细胞表现出较好的抗增殖活性。
基金Project supported by the Scientific Research Foundation of Hunan Provincial Education Department(No.23B0650)the Natural Science Foundation of Hunan Province(No.2022JJ30418)+1 种基金the Key Scientific Research Foundation of Hunan University of Arts and Science(No.22ZD04)the Innovation and Entrepreneurship Training Program for College Students of Hunan University of Arts and Science(No.XDC202318)。
文摘An efficient visible-light-induced radical cascade azidation/cyclization of 2-aryl indoles with trimethylsilyl azide(TMSN3)has been developed using organic dye Rose Bengal as the photocatalyst.This method did not require metal catalysts and additives,and used air as the oxidant to obtain diverse indolo[2,1-a]isoquinolin-6(5H)-ones in moderate to good yields.Mechanistic studies demonstrated that the reaction proceeded via a radical pathway.
基金supported by the National Key R&D Program of China (2017YFA0207302)the National Natural Science Foundation of China (21332007, 21672176)+1 种基金the Natural Science Foundation of Fujian Province, China (2017J01021)the Program for Changjiang Scholars and Innovative Research Team in University of Ministry of Education, China
文摘Employing triflic anhydride/2-fluoropyridine as an activation system, the coupling reactions of secondary N-aryl amides with terminal alkynes yielded substituted quinolines in moderate to excellent yields. The reaction tolerated both electron-donating and electron-withdrawing groups at the benzamide moiety. Electron-rich aryl acetylenes served as excellent coupling partners, and aliphatic terminal alkynes such as cyclopropyl and conjugate vinyl acetylenes could also be used as reaction partners. By means of 2 D NMR techniques(heteronuclear multiple bond correlation(HMBC), heteronuclear single quantum correlation(HSQC)),nitrilium ions were probed as reactive intermediates which are in contrast with that suggested by Movassaghi on the basis of in situ IR monitoring experiments. On the basis of these results, a plausible mechanism for the formation of quinolines was suggested.
基金National Natural Science Foundation of China(Grant No. 20802005 and 20972007)the National Basic Research Program of China (973 Program, Grant No. 2010CB833200)
文摘Efforts toward the total synthesis of indolactam V via CuI-mediated inter- and intra-molecular N-arylation of 4-iodotryptophan derivatives for the introduction of 4-valine moiety from natural L-valine are described. Meanwhile, the efficient synthesis of several pyrroloquinoline derivatives by taking advantage of the CuI-catalyzed intramolecular N-arylation reaction of 4-iodotryptophan is disclosed.
