4-ethyl-4H-furo[3,2-b]indole-2-carboxylic acid | 95612-14-9

• 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: 4-ethyl-4H-furo[3,2-b]indole-2-carboxylic acid
• 英文别名: 4-ethylfuro[3,2-b]indole-2-carboxylic acid
• CAS: 95612-14-9
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: SIAYUIDDKAOHJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-ethyl-4H-furo[3,2-b]indole-2-carboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 0.5h， 以53%的产率得到4-ethyl-furo[3,2-b]indole-2-carbonyl chloride
  参考文献：
  名称：

  Furo(3,2-b)indole derivatives. I. Synthesis and analgesic and anti-inflammatory activities of 4,6-disubstituted-furo(3,2-b)indole-2-carboxamide derivatives.

  摘要：

  合成了N-(3-哌啶丙基)-4, 6-二取代呋喃[3, 2-b]吲哚-2-羧酰胺衍生物，并利用小鼠醋酸扭体法和大鼠卡拉胶水肿法对其镇痛和抗炎活性进行了研究。部分化合物在动物模型中显示出显著的镇痛和抗炎活性。

  DOI：

  10.1248/cpb.32.4271
• 作为产物：
  描述：

  Methyl-4H-furo<3,2-b>-indol-2-carboxylat 在 sodium hydride 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.41h， 生成 4-ethyl-4H-furo[3,2-b]indole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and anticancer activity of 2,4-disubstituted furo[3,2-b]indole derivatives

  摘要：

  We synthesized and evaluated a series of 2,4-disubstituted furo[3,2-b]indole derivatives for anticancer activity and established the structure activity relationships (SARs) of these compounds. Among all tested compounds, we found (5-((2-(hydroxymethyl)-4H-furo[3,2-b]indol-4-yl)methyl)furan-2-yl) methanol (10a) to be the most promising agent. In screening against NCI-60 human tumor cell lines, 10a exhibited highly selective anticancer activity and significant inhibitory activity against A498 renal cancer cells. Our COMPARE analysis results suggest that the 10a fingerprint is similar to that of NSC-754549, which is an isostere of YC-1. We further confirmed the significant antitumor activity of compound 10a with tests in the A498 xenograft nude mice model. Therefore, compound 10a should be further developed as a new drug candidate for treating renal cancer. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.012

文献信息

• NAKASHIMA, YOSHIMOTO;KAWASHIMA, YUTAKA;AMANUMA, FUSAO;SOTA, KAORU;TANAKA,+, CHEM. AND PHARM. BULL., 1984, 32, N 11, 4271-4280
  作者：NAKASHIMA, YOSHIMOTO、KAWASHIMA, YUTAKA、AMANUMA, FUSAO、SOTA, KAORU、TANAKA,+

  DOI：——

  日期：——