(3-benzyloxy-4,5-dimethoxyphenyl)-(6-methoxy-1H-indol-3-yl)methanone | 1176026-91-7

• 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: (3-benzyloxy-4,5-dimethoxyphenyl)-(6-methoxy-1H-indol-3-yl)methanone
• 英文别名: (3,4-dimethoxy-5-phenylmethoxyphenyl)-(6-methoxy-1H-indol-3-yl)methanone
• CAS: 1176026-91-7
• 化学式: C₂₅H₂₃NO₅
• 分子量: 417.461
• InChiKey: SKNLFAMIRFZOCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-benzyloxy-4,5-dimethoxyphenyl)-(6-methoxy-1H-indol-3-yl)methanone 在 10% palladium on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 3'-Desmethyl-BPR0L075
  参考文献：
  名称：

  Synthesis and Evaluation of 3-Aroylindoles as Anticancer Agents: Metabolite Approach

  摘要：

  BPR0L075 (2) is a potential anticancer drug candidate designed from Combretastatin A-4 (1) based on the bioisosterism principle. Metabolites of 2, proposed from in vitro human microsome studies, were synthesized, leading to the identification of metabolitc-derived analogue 10 with 40-350 pM potency against various cancer cell lines. Insights gained from the major inactive metabolite of 2 led to the development of 29, with better pharmacokinetics and improved potency in the tumor xenograft model than 2.

  DOI：

  10.1021/jm900060s
• 作为产物：
  描述：

  6-甲氧基吲哚 、 3-benzyloxy-4,5-dimethoxybenzoyl chloride 在 乙基溴化镁 、 zinc(II) chloride 、 aluminum (III) chloride 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (3-benzyloxy-4,5-dimethoxyphenyl)-(6-methoxy-1H-indol-3-yl)methanone
  参考文献：
  名称：

  Synthesis and Evaluation of 3-Aroylindoles as Anticancer Agents: Metabolite Approach

  摘要：

  BPR0L075 (2) is a potential anticancer drug candidate designed from Combretastatin A-4 (1) based on the bioisosterism principle. Metabolites of 2, proposed from in vitro human microsome studies, were synthesized, leading to the identification of metabolitc-derived analogue 10 with 40-350 pM potency against various cancer cell lines. Insights gained from the major inactive metabolite of 2 led to the development of 29, with better pharmacokinetics and improved potency in the tumor xenograft model than 2.

  DOI：

  10.1021/jm900060s

文献信息

• Synthesis and Evaluation of 3-Aroylindoles as Anticancer Agents: Metabolite Approach
  作者：Yu-Shan Wu、Mohane Selvaraj Coumar、Jang-Yang Chang、Hsu-Yi Sun、Fu-Ming Kuo、Ching-Chuan Kuo、Ying-Jun Chen、Chi-Yen Chang、Chia-Ling Hsiao、Jing-Ping Liou、Ching-Ping Chen、Hsien-Tsung Yao、Yi-Kun Chiang、Uan-Kang Tan、Chiung-Tong Chen、Chang-Ying Chu、Su-Ying Wu、Teng-Kuang Yeh、Chin-Yu Lin、Hsing-Pang Hsieh

  DOI：10.1021/jm900060s

  日期：2009.8.13

  BPR0L075 (2) is a potential anticancer drug candidate designed from Combretastatin A-4 (1) based on the bioisosterism principle. Metabolites of 2, proposed from in vitro human microsome studies, were synthesized, leading to the identification of metabolitc-derived analogue 10 with 40-350 pM potency against various cancer cell lines. Insights gained from the major inactive metabolite of 2 led to the development of 29, with better pharmacokinetics and improved potency in the tumor xenograft model than 2.