thiophene-2-carboxylic acid {4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-indole-1-carbothioyl} amide | 1070956-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: thiophene-2-carboxylic acid {4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-indole-1-carbothioyl} amide
• 英文别名: N-[4-[5-(4-chlorophenoxy)pentoxy]-2,3-dihydroindole-1-carbothioyl]thiophene-2-carboxamide
• CAS: 1070956-12-5
• 化学式: C₂₅H₂₅ClN₂O₃S₂
• 分子量: 501.07
• InChiKey: IZVZGGWSGPHOPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-1H-indole 、 thiophene-2-carbonyl isothiocyanate 以 丙酮 为溶剂， 反应 8.0h， 生成 thiophene-2-carboxylic acid {4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-indole-1-carbothioyl} amide
  参考文献：
  名称：

  Design and synthesis of indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives as novel HCV inhibitors

  摘要：

  An efficient synthetic methodology to provide indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives is described. These conformationally restricted heterobicyclic scaffolds were evaluated as a novel class of HCV inhibitors. Introduction of an acyl group at the NH2 of the thiourea moiety has been found to enhance inhibitory activity. The chain length and the position of the alkyl group on the indoline aromatic ring markedly influenced anti-HCV activity. The indoline scaffold was more potent than the corresponding indole and tetrahydroquinoline scaffolds and analogue 31 displayed excellent activity (EC50 = 510 nM) against HCV without significant cytotoxicity (CC50 > 50 mu M). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.009

文献信息

• HEPATITIS C VIRUS INHIBITORS
  申请人：Chern Jyh-Haur

  公开号：US20080255189A1

  公开（公告）日：2008-10-16

  A compound of the following formula: in which R 1 , R 2 , R 3 , U, V, T, W, X, Y, Z, m, n, p, x, y, and z are as defined herein. Also disclosed are (1) a pharmaceutical composition containing such a compound, and (2) a method for treating Hepatitis C virus infection using such a compound.

  一个具有以下公式的化合物：其中R1、R2、R3、U、V、T、W、X、Y、Z、m、n、p、x、y和z如本文所定义。还披露了（1）含有这种化合物的药物组合物，以及（2）使用这种化合物治疗丙型肝炎病毒感染的方法。
• US7985763B2
  申请人：——

  公开号：US7985763B2

  公开（公告）日：2011-07-26
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：NAT HEALTH RESEARCH INSTITUTES

  公开号：WO2008124300A1

  公开（公告）日：2008-10-16

  [EN] A compound having the formula shown in the application. Also disclosed are (1) a pharmaceutical composition containing such a compound, and (2) a method for treating Hepatitis C virus infection using such a compound.
  [FR] L'invention a trait à un composé ayant la formule indiquée dans la demande, ainsi qu'à (1) une composition pharmaceutique contenant ce composé, et (2) un procédé permettant de traiter les malades atteints du virus de l'hépatite C grâce à ce composé.
• Design and synthesis of indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives as novel HCV inhibitors
  作者：Iou-Jiun Kang、Li-Wen Wang、Sheng-Ju Hsu、Chung-Chi Lee、Yen-Chun Lee、Yen-Shian Wu、Tsu-An Hsu、Andrew Yueh、Yu-Sheng Chao、Jyh-Haur Chern

  DOI：10.1016/j.bmcl.2009.06.009

  日期：2009.8

  An efficient synthetic methodology to provide indole, 2,3-dihydro-indole, and 3,4-dihydro-2H-quinoline-1-carbothioic acid amide derivatives is described. These conformationally restricted heterobicyclic scaffolds were evaluated as a novel class of HCV inhibitors. Introduction of an acyl group at the NH2 of the thiourea moiety has been found to enhance inhibitory activity. The chain length and the position of the alkyl group on the indoline aromatic ring markedly influenced anti-HCV activity. The indoline scaffold was more potent than the corresponding indole and tetrahydroquinoline scaffolds and analogue 31 displayed excellent activity (EC50 = 510 nM) against HCV without significant cytotoxicity (CC50 > 50 mu M). (C) 2009 Elsevier Ltd. All rights reserved.