N-[4-[5-(4-chlorophenoxy)pentoxy]-2,3-dihydroindole-1-carbothioyl]butanamide | 1186137-92-7

• 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: N-[4-[5-(4-chlorophenoxy)pentoxy]-2,3-dihydroindole-1-carbothioyl]butanamide
• CAS: 1186137-92-7
• 化学式: C₂₄H₂₉ClN₂O₃S
• 分子量: 461.025
• InChiKey: XWTDPWGTCFOXMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-butanoyl isothiocyanate 、 4-[5-(4-chloro-phenoxy)-pentyloxy]-2,3-dihydro-1H-indole 以 丙酮 为溶剂， 反应 8.0h， 生成 N-[4-[5-(4-chlorophenoxy)pentoxy]-2,3-dihydroindole-1-carbothioyl]butanamide
  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

• 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.