Methyl 1-phenyl-3h-benzothieno[2,3-e]indole-2-carboxylate | 1037600-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: Methyl 1-phenyl-3h-benzothieno[2,3-e]indole-2-carboxylate
• 英文别名: methyl 1-phenyl-3H-[1]benzothiolo[2,3-e]indole-2-carboxylate
• CAS: 1037600-84-2
• 化学式: C₂₂H₁₅NO₂S
• 分子量: 357.433
• InChiKey: VADNDPHLWBDBSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-N-(tert-butoxycarbonyl)-β-(dibenzothien-4-yl)dehydrophenylalanine methyl ester 在 palladium diacetate copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以37%的产率得到Methyl 3-(dibenzothien-4-yl)indole-2-carboxylate
  参考文献：
  名称：

  Synthesis of new heteroaryl and heteroannulated indoles from dehydrophenylalanines: Antitumor evaluation

  摘要：

  A 3-(dibenzothien-4-yl) indole and a phenylbenzothienoindole or a 3-(dibenzofur-4-yl) indole and a phenylbenzofuroindole were prepared by a metal-assisted C-N intramolecular cyclization of the methyl esters of N-Boc-(E)or(Z)-beta-dibenzothien-4-yl or beta-dibenzofur-4-yl dehydrophenylalanines. The latter were obtained by Suzuki cross-coupling of the methyl esters of N-Boc-(E) or (Z)-beta-bromodehydrophenylalanines with dibenzothien-4-yl or dibenzofur-4-yl boronic acids, in high yields. The intramolecular cyclization from E or Z pure Suzuki-coupling products gave the corresponding heteroaryl and heteroannulated indoles, in different ratios, by either direct cyclization or cyclization after isomerisation. Three of the cyclized compounds, the two heteroarylindoles and the phenylbenzothienoindole, were evaluated for their capacity to inhibit the in vitro growth of three human tumor cell lines, MCF-7 ( breast adenocarcinoma), NCI-H460 ( non-small cell lung cancer), and SF-268 (CNS cancer). The methyl 3-(dibenzothien-4-yl) indole-2-carboxylate was the most potent compound with GI(50) values ranging from 11 to 17 mu M. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.004

文献信息

• Synthesis of new heteroaryl and heteroannulated indoles from dehydrophenylalanines: Antitumor evaluation
  作者：Maria-João R.P. Queiroz、Ana S. Abreu、M. Solange D. Carvalho、Paula M.T. Ferreira、Nair Nazareth、M. São-José Nascimento

  DOI：10.1016/j.bmc.2008.04.004

  日期：2008.5

  A 3-(dibenzothien-4-yl) indole and a phenylbenzothienoindole or a 3-(dibenzofur-4-yl) indole and a phenylbenzofuroindole were prepared by a metal-assisted C-N intramolecular cyclization of the methyl esters of N-Boc-(E)or(Z)-beta-dibenzothien-4-yl or beta-dibenzofur-4-yl dehydrophenylalanines. The latter were obtained by Suzuki cross-coupling of the methyl esters of N-Boc-(E) or (Z)-beta-bromodehydrophenylalanines with dibenzothien-4-yl or dibenzofur-4-yl boronic acids, in high yields. The intramolecular cyclization from E or Z pure Suzuki-coupling products gave the corresponding heteroaryl and heteroannulated indoles, in different ratios, by either direct cyclization or cyclization after isomerisation. Three of the cyclized compounds, the two heteroarylindoles and the phenylbenzothienoindole, were evaluated for their capacity to inhibit the in vitro growth of three human tumor cell lines, MCF-7 ( breast adenocarcinoma), NCI-H460 ( non-small cell lung cancer), and SF-268 (CNS cancer). The methyl 3-(dibenzothien-4-yl) indole-2-carboxylate was the most potent compound with GI(50) values ranging from 11 to 17 mu M. (C) 2008 Elsevier Ltd. All rights reserved.