2-amino-3-cyano-(3′-bromophenyl)-7-methoxy-4H-chromene

• 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-(3′-bromophenyl)-7-methoxy-4H-chromene
• 英文别名: 2-amino-4-(3'-bromophenyl)-7-methoxy-4H-chromene-3-carbonitrile；2-amino-3-cyano-7-methoxy-4-(3-bromophenyl)-4H-chromene；2-amino-4-(3-bromophenyl)-7-methoxy-4H-chromene-3-carbonitrile
• 化学式: C₁₇H₁₃BrN₂O₂
• 分子量: 357.206
• InChiKey: AZWHYMCLZCJZKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲氧基苯酚 、 间溴苯甲醛 以27%的产率得到2-amino-3-cyano-(3′-bromophenyl)-7-methoxy-4H-chromene
  参考文献：
  名称：

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

  摘要：

  本发明涉及被一般式I表示的取代的4H-香豆素及其类似物： 1 其中R 1 -R 5 ，A，Y和Z在此处被定义。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各种临床病况中发生细胞死亡，其中异常细胞的不受控制的生长和传播。

  公开号：

  US20030065018A1

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。
• SUBSTITUTED 4H-CHROMENES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF
  申请人：Cai Xiong Sui

  公开号：US20060035925A1

  公开（公告）日：2006-02-16

  The present invention is directed to substituted 4H-chromenes and analogs thereof, represented by the general Formula I: wherein R 1 -R 5 , A, 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.

  本发明涉及代替的4H-香豆素及其类似物，由通式I表示：其中R1-R5，A，Y和Z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用于诱导在各种临床情况下不受控制的异常细胞的生长和扩散引起的细胞死亡。
• 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 high-throughput screening assay. 2. Structure–activity relationships of the 7- and 5-, 6-, 8-positions
  作者：William Kemnitzer、Shailaja Kasibhatla、Songchun Jiang、Hong Zhang、Jianghong Zhao、Shaojuan Jia、Lifen Xu、Candace Crogan-Grundy、Réal Denis、Nancy Barriault、Louis Vaillancourt、Sylvie Charron、Jennifer Dodd、Giorgio Attardo、Denis Labrecque、Serge Lamothe、Henriette Gourdeau、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2005.07.066

  日期：2005.11

  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 4-aryl-4H-chromenes with modifications at the 7- and 5-, 6-, 8-positions. It was found that a small hydrophobic group, such as NMe2, NH2, NHEt, and OMe, is preferred at the 7-position. Di-substitution at either the 5,7-positions or the 6,7-positions generally led to a large decrease in potency. Di-substitution at the 7,8-positions, in general, was found to result in potent compounds. 7-NMe2, 7-NHEt, 7-OMe, and 7,8-di-NH2 analogs were found to have similar SAR for the 4-aryl group, and several 7-substituted and 7,8-di-substituted analogs were found to have similar potencies as the lead compound MX58151 (2a) both as caspase activators and inhibitors of cell proliferation. (c) 2005 Elsevier Ltd. All rights reserved.
• 4-Aryl-4<i>H</i>-Chromene-3-Carbonitrile Derivates: Synthesis and Preliminary Anti-Breast Cancer Studies
  作者：Nancy Thomas、Subin Mary Zachariah、Prasanna Ramani

  DOI：10.1002/jhet.2483

  日期：2016.11

  A series of new 4‐aryl‐4H‐chromene‐3‐carbonitrile derivatives were obtained by one‐pot synthesis using substituted benzaldehydes, malononitrile, and substituted phenols. All the synthesized compounds (1a, 1b, 1c, 1d, 1e) were screened in vitro for antioxidant and anticancer activities. Compounds 1c, 1d, 1e showed significant antioxidant activity in nitric oxide free radical scavenging method while compounds 1c and 1e showed significant activity in hydrogen peroxide free radical scavenging method. The other compounds showed significant to moderate activities in both the methods in comparison with ascorbic acid and butylated hydroxytoluene as standards. Compounds 1c, 1d, 1e exhibited good anticancer activity, using Michigan Cancer Foundation‐7 (MCF‐7) cell line, compared with those of other synthesized compounds.