2-Amino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-7,8,9,10-tetrahydro-4H-naphtho[1,2-b]pyran

• 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: 2-Amino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-7,8,9,10-tetrahydro-4H-naphtho[1,2-b]pyran
• 英文别名: 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-7,8,9,10-tetrahydro-4H-benzo[h]chromene-3-carbonitrile
• 化学式: C₂₂H₂₁BrN₂O₃
• 分子量: 441.324
• InChiKey: NMOMHQFVCUDVJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-dimethoxy-5-bromobenzylidenemalinonitrile 、 四氢萘酚 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以1.4%的产率得到2-Amino-3-cyano-4-(3-bromo-4,5-dimethoxyphenyl)-7,8,9,10-tetrahydro-4H-naphtho[1,2-b]pyran
  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：

  公开号：

  EP1230232B1

文献信息

• Substituted 4H-chromene and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Drewe A. John

  公开号：US20050154015A1

  公开（公告）日：2005-07-14

  The present invention is directed to substituted 4H-chromene and analogs thereof, represented by the general Formula I: wherein A, B, X, Y, Z and R 5 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.

  本发明涉及取代的4H-香豆素及其类似物，通式如下：其中A、B、X、Y、Z和R5在此定义。本发明还涉及发现具有通式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以用于诱导各种临床情况下不受控制的异常细胞的生长和扩散导致的细胞死亡。
• Discovery of 4-Aryl-4<i>H</i>-chromenes as a New Series of Apoptosis Inducers Using a Cell- and Caspase-Based High-Throughput Screening Assay. 3. Structure−Activity Relationships of Fused Rings at the 7,8-Positions
  作者：William Kemnitzer、John Drewe、Songchun Jiang、Hong Zhang、Jianghong Zhao、Candace Crogan-Grundy、Lifen Xu、Serge Lamothe、Henriette Gourdeau、Réal Denis、Ben Tseng、Shailaja Kasibhatla、Sui Xiong Cai

  DOI：10.1021/jm070216c

  日期：2007.6.1

  As a continuation of our efforts to discover and develop the apoptosis-inducing 4-aryl-4H-chromenes as novel anticancer agents, we explored the SAR of fused rings at the 7,8-positions. It was found that a five-member aromatic ring, such as pyrrolo with nitrogen at either the 7- or 9-position, is preferred. A six-member aromatic ring, such as benzo or pyrido, also led to potent compounds. The SAR of the 4-aryl group was found to be similar for chromenes with a fused ring at the 7,8-positions. These compounds were found to inhibit tubulin polymerization, indicating that cyclization of the 7,8-positions into a ring does not change the mechanism of action. Compound 2h was identified to be a highly potent apoptosis inducer with an EC50 of 5 nM and a highly potent inhibitor of cell proliferation with a GI(50) of 8 nM in T47D cells.
• 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.