(6-methoxy-2-methylindolizin-1-yl)-(3,4,5-trimethoxyphenyl)methanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6-methoxy-2-methylindolizin-1-yl)-(3,4,5-trimethoxyphenyl)methanone
• 英文别名: (6-methoxy-2-methyl-indolizin-1-yl)-(3,4,5-trimethoxy-phenyl)-methanone
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: FWUPKAVKWPSTGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基-6-甲基吡啶 在 potassium tert-butylate 、 碳酸氢钠 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 19.33h， 生成 (6-methoxy-2-methylindolizin-1-yl)-(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Scaffold-Hopping Strategy: Synthesis and Biological Evaluation of 5,6-Fused Bicyclic Heteroaromatics To Identify Orally Bioavailable Anticancer Agents

  摘要：

  Utilizing scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 (1), an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shuffling of the nitrogen from the N-1 position or by insertion of one or two nitrogen atoms into the indole core of 1. Among these, 7-azaindole core 12 showed potent in vitro anticancer activity and improved oral bioavailability (F = 35%) compared with 1 (F < 10%).

  DOI：

  10.1021/jm101027s

文献信息

• Anti-tumor compounds
  申请人：Hsieh Hsing-Pang

  公开号：US20060148801A1

  公开（公告）日：2006-07-06

  Compounds of the following formula: wherein A, D, Q, T, U, V, W, X, Y, Z, R 1 , and ---- are as defined herein. This invention also relates to a method of inhibiting tubulin polymerization, or treating cancer or an angiogenesis-related disorder with one of these compounds.

  以下化合物的结构如下： 其中A、D、Q、T、U、V、W、X、Y、Z、R1和----在此处定义。本发明还涉及一种通过其中一种化合物抑制微管聚合，或治疗癌症或血管生成相关疾病的方法。
• ANTI-TUMOR COMPOUNDS
  申请人：National Health Research Institutes

  公开号：EP1838711A2

  公开（公告）日：2007-10-03
• US7456289B2
  申请人：——

  公开号：US7456289B2

  公开（公告）日：2008-11-25
• [EN] ANTI-TUMOR COMPOUNDS<br/>[FR] COMPOSES ANTITUMORAUX
  申请人：NAT HEALTH RESEARCH INSTITUTES

  公开号：WO2006074041A2

  公开（公告）日：2006-07-13

  [EN] Compounds of formula (I); wherein A, D, Q, T, U, V, W, X, Y, Z, R₁, and formula (II) are as defined herein. This invention also relates to a method of inhibiting tubulin polymerization, or treating cancer or an angiogenesis-related disorder with one of these compounds.
  [FR] L'invention porte sur des composés de formule (I) dans laquelle A, D, Q, T, U, V, W, X, Y, Z, R₁, et de formule (II) qui sont tels que définis dans la demande. Cette invention porte également sur une méthode d'inhibition de la polymérisation de la tubuline ou du traitement du cancer ou d'une maladie liée à l'angiogenèse avec l'un de ces composés.
• Scaffold-Hopping Strategy: Synthesis and Biological Evaluation of 5,6-Fused Bicyclic Heteroaromatics To Identify Orally Bioavailable Anticancer Agents
  作者：Yen-Shih Tung、Mohane Selvaraj Coumar、Yu-Shan Wu、Hui-Yi Shiao、Jang-Yang Chang、Jing-Ping Liou、Paritosh Shukla、Chun-Wei Chang、Chi-Yen Chang、Ching-Chuan Kuo、Teng-Kuang Yeh、Chin-Yu Lin、Jian-Sung Wu、Su-Ying Wu、Chun-Chen Liao、Hsing-Pang Hsieh

  DOI：10.1021/jm101027s

  日期：2011.4.28

  Utilizing scaffold-hopping drug-design strategy, we sought to identify a backup drug candidate for BPR0L075 (1), an indole-based anticancer agent. For this purpose, 5,6-fused bicyclic heteroaromatic scaffolds were designed and synthesized through shuffling of the nitrogen from the N-1 position or by insertion of one or two nitrogen atoms into the indole core of 1. Among these, 7-azaindole core 12 showed potent in vitro anticancer activity and improved oral bioavailability (F = 35%) compared with 1 (F < 10%).