3-Cyano-7-dimethylamino-2-succinimido-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene | 339062-86-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 3-Cyano-7-dimethylamino-2-succinimido-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene
• 英文别名: 4-(3-bromo-4,5-dimethoxyphenyl)-7-(dimethylamino)-2-(2,5-dioxopyrrolidin-1-yl)-4H-chromene-3-carbonitrile
• CAS: 339062-86-1
• 化学式: C₂₄H₂₂BrN₃O₅
• 分子量: 512.36
• InChiKey: RTJQCAYFBRVPHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  丁二酰氯 、 2-amino-4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-7-dimethyl-amino-4H-chromene 生成 3-Cyano-7-dimethylamino-2-succinimido-4-(3-bromo-4,5-dimethoxyphenyl)-4H-chromene
  参考文献：
  名称：

  Substituted 4H-chromene and analogs as activators of caspases and inducers of apoptosis and the use thereof

  摘要：

  本发明涉及取代的4H-香豆素及其类似物，由一般式I表示：其中A、B、X、Y、Z和R5在此定义。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在各种临床情况下诱导细胞死亡，其中发生异常细胞的不受控制的生长和扩散。

  公开号：

  US06906203B1

文献信息

• SUBSTITUTED 4H-CHROMENE AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF
  申请人：Cytovia, Inc.

  公开号：EP1230232B1

  公开（公告）日：2004-02-25
• Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based HTS assay. Part 5: Modifications of the 2- and 3-positions
  作者：William Kemnitzer、Songchun Jiang、Yan Wang、Shailaja Kasibhatla、Candace Crogan-Grundy、Monica Bubenik、Denis Labrecque、Real Denis、Serge Lamothe、Giorgio Attardo、Henriette Gourdeau、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2007.11.078

  日期：2008.1

  As a continuation of our efforts to discover and develop apoptosis inducing 4-aryl-4H-chromenes as novel anticancer agents, we explored modifications at the 2- and 3-positions. It was found that replacement of the 3-cyano group by an ester, including metbyl and ethyl ester, resulted in > 200-fold reduction of activity. Conversion of the 2-amino group into an amide or urea resulted in 4- to 10-fold drop of activity. Similarly, converting the 2-amino group into a hydrogen resulted in 4- to 10-fold reduction of activity. Compound 3d was highly active with an EC50 value of 29 nM and a GI(50) value of 6 nM in T47D cells. Importantly, the 2H analog 3d was found to be much more stable under acidic conditions compared to the 2-NH2 analog 3b, suggesting that 2-H analogs might have better bioavailability than the 2-NH2 analogs. (c) 2007 Elsevier Ltd. All rights reserved.
• US6906203B1
  申请人：——

  公开号：US6906203B1

  公开（公告）日：2005-06-14
• US7507762B2
  申请人：——

  公开号：US7507762B2

  公开（公告）日：2009-03-24
• [EN] SUBSTITUTED 4H-CHROMENE AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF<br/>[FR] 4H-CHROMENE SUBSTITUE ET SES ANALOGUES EN TANT QU'ACTIVATEURS DE CASPASES ET QU'INDUCTEURS D'APOPTOSE AINSI QUE LEUR UTILISATION
  申请人：CYTOVIA INC

  公开号：WO2001034591A2

  公开（公告）日：2001-05-17

  The present invention is directed to substituted 4H-chromene and analogs thereof, represented by general Formula (I), wherein A, B, X, Y, Z and R5 are defined herein. The present invention also relates to the discovery that compounds having Formula (I) are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.