ethyl 3-bromo-1-benzo[b]thiophene-2-carboxylate

• 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: ethyl 3-bromo-1-benzo[b]thiophene-2-carboxylate
• 英文别名: ethyl 3-bromobenzo[b]thiophene-2-carboxylate；ethyl 3-bromo-1-benzothiophene-2-carboxylate
• 化学式: C₁₁H₉BrO₂S
• 分子量: 285.161
• InChiKey: RLUIYHRFSJDYFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3-bromo-1-benzo[b]thiophene-2-carboxylate 在 aluminum oxide 、 palladium diacetate 、 sodium hydroxide 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成 N-benzo[b]thien-3-yl-N-(4-methoxyphenyl)amine
  参考文献：
  名称：

  缺电子或相对富电子苯并[b]噻吩基溴的钯催化胺化-抗菌活性和SAR的初步研究

  摘要：

  在 Pd(OAc)2 存在下，通过 3-溴苯并 [b] 噻吩-2-羧酸乙酯与苯胺和 5-氨基吲哚的钯催化胺化反应，制备了苯并 [b] 噻吩系列中的几种二芳基胺, BINAP 和 Cs2CO3 的甲苯溶液。相对于用 3-溴苯并 [b] 噻吩进行的反应，苯并 [b] 噻吩部分 2-位酯基的存在增加了产率并缩短了加热时间。当使用氨基吡啶代替苯胺时，在胺化反应中需要将配体和溶剂改为XANTHPHOS和二恶烷。对于 2-氨基吡啶，发生了单锅 CN 偶联和涉及吡啶环氮原子的分子内环化，失去了

  DOI：

  10.1002/ejoc.200400218
• 作为产物：
  描述：

  2-硝基苯甲腈 在 亚硝酸特丁酯 、 水 、 potassium hydroxide 、 copper(ll) bromide 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 反应 3.0h， 生成 ethyl 3-bromo-1-benzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[b]thiophenes and Thieno[2,3-b]pyridines as New Potent Anticancer Agents

  摘要：

  Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3',4',5'-trimethoxyanilino)benzo[b]thiophene and thieno[2,3-b]pyridine molecular skeletons were synthesized and evaluated for antiproliferative activity on a panel of cancer cell lines, inhibition of tubulin polymerization, cell cycle effects, and in vivo potency. Antiproliferative activity was strongly dependent on the position of the methyl group on the benzene portion of the benzo[b]thiophene nucleus, with the greatest activity observed when the methyl was located at the C-6 position. Also, in the smaller thieno[2,3-b]pyridine series, the introduction of the methyl group at the C-6 position resulted in improvement of antiproliferative activity to the nanomolar level. The most active compounds (4i and 4n) did not induce cell death in normal human lymphocytes, suggesting that the compounds may be selective against cancer cells. Compound 4i significantly inhibited in vivo the growth of a syngeneic hepatocellular carcinoma in Balb/c mice.

  DOI：

  10.1021/jm400043d

文献信息

• Antifungal activity of synthetic di(hetero)arylamines based on the benzo[b]thiophene moiety
  作者：Eugénia Pinto、Maria-João R.P. Queiroz、Luís A. Vale-Silva、João F. Oliveira、Agathe Begouin、Jeanne-Marie Begouin、Gilbert Kirsch

  DOI：10.1016/j.bmc.2008.07.042

  日期：2008.9

  The antifungal activity of several di(hetero)arylamine derivatives of the benzo[b]thiophene system was evaluated against clinically relevant Candida, Aspergillus, and dermatophyte species by a broth macrodilution test based on CLSI ( formerly NCCLS) guidelines. The most active compound showed a broad spectrum of activity ( against all tested fungal strains, including fluconazole-resistant fungi), with particularly low MICs for dermatophytes. Results from the inhibition of the dimorphic transition in Candida albicans and flow cytometry studies further confirmed their biological activity. With this study it was possible to establish some structure-activity relationships (SARs). The hydroxy groups proved to be essential for the activity in the aryl derivatives. Furthermore, the spectrum of activity in the pyridine derivatives was broadened by the absence of the ester group on position 2 of the benzo[b]thiophene system. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of 2-(Alkoxycarbonyl)-3-Anilinobenzo[<i>b</i>]thiophenes and Thieno[2,3-<i>b</i>]pyridines as New Potent Anticancer Agents
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Kimatrai Salvador、Delia Preti、Mojgan Aghazadeh Tabrizi、Marcella Bassetto、Andrea Brancale、Ernest Hamel、Ignazio Castagliuolo、Roberta Bortolozzi、Giuseppe Basso、Giampietro Viola

  DOI：10.1021/jm400043d

  日期：2013.3.28

  Two new series of inhibitors of tubulin polymerization based on the 2-(alkoxycarbonyl)-3-(3',4',5'-trimethoxyanilino)benzo[b]thiophene and thieno[2,3-b]pyridine molecular skeletons were synthesized and evaluated for antiproliferative activity on a panel of cancer cell lines, inhibition of tubulin polymerization, cell cycle effects, and in vivo potency. Antiproliferative activity was strongly dependent on the position of the methyl group on the benzene portion of the benzo[b]thiophene nucleus, with the greatest activity observed when the methyl was located at the C-6 position. Also, in the smaller thieno[2,3-b]pyridine series, the introduction of the methyl group at the C-6 position resulted in improvement of antiproliferative activity to the nanomolar level. The most active compounds (4i and 4n) did not induce cell death in normal human lymphocytes, suggesting that the compounds may be selective against cancer cells. Compound 4i significantly inhibited in vivo the growth of a syngeneic hepatocellular carcinoma in Balb/c mice.
• Palladium-Catalysed Amination of Electron-Deficient or Relatively Electron-Rich Benzo[b]thienyl Bromides− Preliminary Studies of Antimicrobial Activity and SARs
  作者：Maria-João R. P. Queiroz、Agathe Begouin、Isabel C. F. R. Ferreira、Gilbert Kirsch、Ricardo C. Calhelha、Sandra Barbosa、Letícia M. Estevinho

  DOI：10.1002/ejoc.200400218

  日期：2004.9

  Several diarylamines in the benzo[b]thiophene series were prepared in good to high yields by palladium-catalysed amination of ethyl 3-bromobenzo[b]thiophene-2-carboxylate with anilines and 5-aminoindole in the presence of Pd(OAc)2, BINAP and Cs2CO3 in toluene. The presence of the ester group at the 2-position of the benzo[b]thiophene moiety increases the yields and lowers the heating times relative

  在 Pd(OAc)2 存在下，通过 3-溴苯并 [b] 噻吩-2-羧酸乙酯与苯胺和 5-氨基吲哚的钯催化胺化反应，制备了苯并 [b] 噻吩系列中的几种二芳基胺, BINAP 和 Cs2CO3 的甲苯溶液。相对于用 3-溴苯并 [b] 噻吩进行的反应，苯并 [b] 噻吩部分 2-位酯基的存在增加了产率并缩短了加热时间。当使用氨基吡啶代替苯胺时，在胺化反应中需要将配体和溶剂改为XANTHPHOS和二恶烷。对于 2-氨基吡啶，发生了单锅 CN 偶联和涉及吡啶环氮原子的分子内环化，失去了