3-(3-bromo-4,5-dimethoxyphenyl)-2-cyanoacrylic acid ethyl ester | 475629-12-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(3-bromo-4,5-dimethoxyphenyl)-2-cyanoacrylic acid ethyl ester
• 英文别名: 3-(3-Bromo-4,5-dimethoxyphenyl)-2-cyano-acrylic acid ethyl ester；ethyl 3-(3-bromo-4,5-dimethoxyphenyl)-2-cyanoprop-2-enoate
• CAS: 475629-12-0
• 化学式: C₁₄H₁₄BrNO₄
• 分子量: 340.173
• InChiKey: XYCMOYUNAUCAOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3-bromo-4,5-dimethoxyphenyl)-2-cyanoacrylic acid ethyl ester 、 4-二甲氨基苯酚 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 3-Cyano-7-dimethylamino-4-(3-bromo-4,5-dimethoxyphenyl)-2-oxo-2H-chromene
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.09.011
• 作为产物：
  描述：

  3-溴-4,5-二甲氧基苯甲醛 、 氰乙酸乙酯 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 3-(3-bromo-4,5-dimethoxyphenyl)-2-cyanoacrylic acid ethyl ester
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.09.011

文献信息

• Substituted coumarins and quinolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20050090526A1

  公开（公告）日：2005-04-28

  The present invention is directed to substituted coumarins and quinolines and analogs thereof, represented by the general Formula I: wherein A, B, X, Y, and Z 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.

  本发明涉及替代香豆素和喹啉及其类似物，其由通式I所表示：其中，A、B、X、Y和Z在此定义。本发明还涉及发现具有I式化合物是caspase激活剂和诱导细胞凋亡剂。因此，本发明的caspase激活剂和诱导细胞凋亡剂可用于诱导在各种临床情况下出现的不受控制的异常细胞的生长和扩散的细胞死亡。
• 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.