3-Cyano-4-(3-methoxy-4,5-methylenedioxyphenyl)-7-methyl-2-oxo-2H-pyrrolo[2,3-h]chromene | 475630-15-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-Cyano-4-(3-methoxy-4,5-methylenedioxyphenyl)-7-methyl-2-oxo-2H-pyrrolo[2,3-h]chromene
• 英文别名: 4-(7-Methoxy-1,3-benzodioxol-5-yl)-7-methyl-2-oxopyrano[2,3-e]indole-3-carbonitrile
• CAS: 475630-15-0
• 化学式: C₂₁H₁₄N₂O₅
• 分子量: 374.353
• InChiKey: SODWOIKKSUXZOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-cyano-2-imino-4-(3-methoxy-4,5-methylenedioxyphenyl)-7-methyl-2H-pyrrolo[2,3-h]chromene 生成 3-Cyano-4-(3-methoxy-4,5-methylenedioxyphenyl)-7-methyl-2-oxo-2H-pyrrolo[2,3-h]chromene
  参考文献：
  名称：

  Substituted coumarins and quinolines and analogs as activators of caspases and inducers of apoptosis and the use thereof

  摘要：

  本发明涉及取代香豆素和喹啉及其类似物，由一般式I：1表示，其中A、B、X、Y和Z在此处定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在出现异常细胞的不受控制的生长和传播的各种临床状况中的细胞死亡。

  公开号：

  US20030114485A1

文献信息

• Discovery of 4-aryl-2-oxo-2H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay
  作者：William Kemnitzer、Songchun Jiang、Hong Zhang、Shailaja Kasibhatla、Candace Crogan-Grundy、Charles Blais、Giorgio Attardo、Real Denis、Serge Lamothe、Henriette Gourdeau、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2008.09.011

  日期：2008.10

  As a continuation of our efforts to discover and develop the apoptosis inducing 4-aryl-4H-chromenes as potential anticancer agents, we explored the removal of the chiral center at the 4-position and prepared a series of 4-aryl-2-oxo-2H-chromenes. It was found that, in general, removal of the chiral center and replacement of the 2-amino group with a 2-oxo group were tolerated and 4-aryl-2-oxo-2H-chromenes exhibited SAR similar to 4-aryl-2-amino-4H-chromenes. The 4-aryl-2-oxo-2H-chromenes with a N-methyl pyrrole fused at the 7,8-positions were highly active with compound 2a having an EC(50) value of 13 nM in T47D cells. It was found that an OMe group was preferred at the 7-positon. 7-NMe(2), 7-NH(2), 7-Cl and 7,8 fused pyrido analogs all had low potency. These 4-aryl-2-oxo-2H-chromenes are a series of potent apoptosis inducers with potential advantage over the 4-aryl-2-amino-4H-chromenes series via elimination of the chiral center at the 4-position. (C) 2008 Elsevier Ltd. All rights reserved.
• US7015328B2
  申请人：——

  公开号：US7015328B2

  公开（公告）日：2006-03-21
• US7235674B2
  申请人：——

  公开号：US7235674B2

  公开（公告）日：2007-06-26