ethyl 5-((1,4-diazepan-1yl)methyl)-1-methyl-2-((phenylsulfonyl)methyl)-1H-indole-3-carboxylate | 1245933-74-7

• 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: ethyl 5-((1,4-diazepan-1yl)methyl)-1-methyl-2-((phenylsulfonyl)methyl)-1H-indole-3-carboxylate
• 英文别名: Ethyl 2-(benzenesulfonylmethyl)-5-(1,4-diazepan-1-ylmethyl)-1-methyl-indole-3-carboxylate；ethyl 2-(benzenesulfonylmethyl)-5-(1,4-diazepan-1-ylmethyl)-1-methylindole-3-carboxylate
• CAS: 1245933-74-7
• 化学式: C₂₅H₃₁N₃O₄S
• 分子量: 469.605
• InChiKey: RXHUFXCFUQIMQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 5-formyl-1-methyl-2-((phenylsulfonyl)methyl)-1H-indole-3-carboxylate 、 1,4-二氮杂环庚烷-1-甲酸叔丁酯 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以83%的产率得到ethyl 5-((1,4-diazepan-1yl)methyl)-1-methyl-2-((phenylsulfonyl)methyl)-1H-indole-3-carboxylate
  参考文献：
  名称：

  Synthesis and anti-hepatitis C virus activity of novel ethyl 1H-indole-3-carboxylates in vitro

  摘要：

  A series of ethyl 1H-indole-3-carboxylates 9a(1-6) and 9b(1-2) were prepared and evaluated in Huh-7.5 cells. Most of the compounds exhibited anti-hepatitis C virus (HCV) activities at low concentration. The selectivity indices of inhibition on entry and replication of compounds 9a(2) (> 10; > 16.7) and 9b(1) (> 6.25; > 16.7) were higher than those of the other evaluated compounds, including the lead compound Arbidol (ARB, 6; 15). Moreover, the selective index of inhibition on entry of compound 9a(3) (> 6.25) was higher than that of ARB (6). Of these three initial hits, compound 9a(2) was the most potent. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.058

文献信息

• Synthesis and anti-hepatitis C virus activity of novel ethyl 1H-indole-3-carboxylates in vitro
  作者：Grazia Sellitto、Aurora Faruolo、Paolo de Caprariis、Sergio Altamura、Giacomo Paonessa、Gennaro Ciliberto

  DOI：10.1016/j.bmc.2010.06.058

  日期：2010.8

  A series of ethyl 1H-indole-3-carboxylates 9a(1-6) and 9b(1-2) were prepared and evaluated in Huh-7.5 cells. Most of the compounds exhibited anti-hepatitis C virus (HCV) activities at low concentration. The selectivity indices of inhibition on entry and replication of compounds 9a(2) (> 10; > 16.7) and 9b(1) (> 6.25; > 16.7) were higher than those of the other evaluated compounds, including the lead compound Arbidol (ARB, 6; 15). Moreover, the selective index of inhibition on entry of compound 9a(3) (> 6.25) was higher than that of ARB (6). Of these three initial hits, compound 9a(2) was the most potent. (C) 2010 Elsevier Ltd. All rights reserved.