(2-benzyl-6-iodo-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acid | 1262779-51-0

• 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: (2-benzyl-6-iodo-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acid
• 英文别名: 2-(2-Benzyl-6-iodo-1-sulfanylidene-3,4-dihydropyrido[3,4-b]indol-9-yl)acetic acid
• CAS: 1262779-51-0
• 化学式: C₂₀H₁₇IN₂O₂S
• 分子量: 476.338
• InChiKey: BQFUDTDZMLXFSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-benzyl-6-iodo-2,3,4,9-tetrahydro-β-carboline-1-thione 在 lithium hydroxide monohydrate 、 水 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (2-benzyl-6-iodo-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel (1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acids as selective inhibitors for AKR1B1

  摘要：

  New substituted (1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acids were designed as the inhibitor of AKR1B1 based upon the structure of rhetsinine, a minor alkaloidal component of Evodia rutaecarpa, and twenty derivatives were synthesized and evaluated. The most active compound of the series was (2-benzyl-6-methoxy-1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7m), which showed comparable inhibitory activity for AKR1B1 (IC50 = 0.15 mu M) with clinically used epalrestat (IC50 = 0.1 mu M). In the view of activity and selectivity, the most potent compound was (2-benzyl-6-carboxy-1-thioxo1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7t), which showed strong inhibitory effect (IC50 = 0.17 mu M) and very high selectivity for AKR1B1 against AKR1A1 (311: 1) and AKR1B10 (253: 1) compared with epalrestat. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.073

文献信息

• Design, synthesis, and biological evaluation of novel (1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acids as selective inhibitors for AKR1B1
  作者：Daisuke Minehira、Daisuke Takeda、Hirokazu Urata、Atsushi Kato、Isao Adachi、Xu Wang、Yuji Matsuya、Kenji Sugimoto、Mayuko Takemura、Satoshi Endo、Toshiyuki Matsunaga、Akira Hara、Jun Koseki、Kayo Narukawa、Shuichi Hirono、Naoki Toyooka

  DOI：10.1016/j.bmc.2011.10.073

  日期：2012.1

  New substituted (1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acids were designed as the inhibitor of AKR1B1 based upon the structure of rhetsinine, a minor alkaloidal component of Evodia rutaecarpa, and twenty derivatives were synthesized and evaluated. The most active compound of the series was (2-benzyl-6-methoxy-1-thioxo-1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7m), which showed comparable inhibitory activity for AKR1B1 (IC50 = 0.15 mu M) with clinically used epalrestat (IC50 = 0.1 mu M). In the view of activity and selectivity, the most potent compound was (2-benzyl-6-carboxy-1-thioxo1,2,3,4-tetrahydro-b-carbolin-9-yl) acetic acid (7t), which showed strong inhibitory effect (IC50 = 0.17 mu M) and very high selectivity for AKR1B1 against AKR1A1 (311: 1) and AKR1B10 (253: 1) compared with epalrestat. (C) 2011 Elsevier Ltd. All rights reserved.