2-amino-3-cyano-4-(3-methylphenyl)-7-(dimethylamino)-4H-benzopyran

• 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-methylphenyl)-7-(dimethylamino)-4H-benzopyran
• 英文别名: 2-Amino-3-cyano-7-dimethylamino-4-(3-methylphenyl)-4H-chromene；2-amino-7-(dimethylamino)-4-(3-methylphenyl)-4H-chromene-3-carbonitrile
• 化学式: C₁₉H₁₉N₃O
• 分子量: 305.379
• InChiKey: KBYMICZYRPSGOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基苯甲醛 、 丙二腈 、 3-羟基-N,N-二甲基苯胺 在 sodium chloride 、 bovine serum albumin 作用下， 以 neat (no solvent) 为溶剂， 以89 %的产率得到2-amino-3-cyano-4-(3-methylphenyl)-7-(dimethylamino)-4H-benzopyran
  参考文献：
  名称：

  2-Amino-3-cyano-4 的机械生物催化快速合成

  摘要：

  通过简单的一锅法反应合成了一系列 2-氨基-3-氰基-4 H-吡喃4a - 4s和5a - 5r ，收率良好。简便的方法依赖于在球磨条件下，在牛血清白蛋白（BSA）作为催化剂存在下，芳香醛、丙二腈和二甲酮或3-（二甲氨基）苯酚的一锅三组分反应。反应在 40 分钟内完成，产率为 80-98%。合成的化合物通过1 H NMR、13 C NMR和ESI-MS进行了表征。

  DOI：

  10.3987/com-21-14608

文献信息

• 一种2-氨基-3-氰基-4H-吡喃类化合物的机械球磨辅助合成方法
  申请人：浙江工业大学

  公开号：CN113620919A

  公开（公告）日：2021-11-09

  本发明涉及化学合成技术领域，为解决现有现有技术下用化学法合成2‑氨基‑3‑氰基‑4H‑吡喃类化合物污染大，所用催化剂制备繁琐的问题，公开了一种2‑氨基‑3‑氰基‑4H‑吡喃类化合物的机械球磨辅助合成方法，包括以下步骤：（a）将底物1、底物2及丙二腈作为原料，加入蛋白质催化剂及助磨剂后进行机械球磨；（b）球磨结束后将反应物刮出，加入溶剂，过滤后经浓缩、柱层析制得2‑氨基‑3‑氰基‑4H‑吡喃类化合物。机械球磨技术有利于反应物分子相互接触，实现无溶剂反应，蛋白类催化剂易得对环境友好。本发明有效地实现了对2‑氨基‑3‑氰基‑4H‑吡喃类化合物的绿色合成，制备条件温和，操作简便，反应速率快。
• 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-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-4<i>H</i>-chromenes as a New Series of Apoptosis Inducers Using a Cell- and Caspase-based High-Throughput Screening Assay. 1. Structure−Activity Relationships of the 4-Aryl Group
  作者：William Kemnitzer、John Drewe、Songchun Jiang、Hong Zhang、Yan Wang、Jianghong Zhao、Shaojuan Jia、John Herich、Denis Labreque、Richard Storer、Karen Meerovitch、David Bouffard、Rabindra Rej、Real Denis、Charles Blais、Serge Lamothe、Giorgio Attardo、Henriette Gourdeau、Ben Tseng、Shailaja Kasibhatla、Sui Xiong Cai

  DOI：10.1021/jm049640t

  日期：2004.12.1

  By applying a novel cell- and caspase-based HTS assay, 2-amino-3-eyano-7-(dimethylamino)4-(3-methoxy-4,5-methylenedioxyphenyl)-4H-chromene (1a) has been identified as a potent apoptosis inducer. Compound la was found to induce nuclear fragmentation and PARP cleavage, as well as to arrest cells at the G(2)/M stage and to induce apoptosis as determined by the flow cytometry analysis assay in multiple human cell lines (e.g. Jurkat, T47D). Through structure-activity relationship (SAR) studies of the 4-aryl group, a 4- and 7-fold increase in potency was obtained from the screening hit la to the lead compounds 2-amino-4-(3-bromo-4,5-dimethoxyphenyl)-3-cyano-7-(dimethylamino)-4H-chromene (1c) and 2-amino-3-cyano-7-(dimethylamino)4-(5-methyl-3-pyridyl)-4H-chromene (4e), with an EC50 of 19 and 11 nM in the caspase activation assay in T47D breast cancer cells, respectively. The 2-amino-4-aryl-3-cyano-7-(dimethylamino)4H-chromenes also were found to be highly active in the growth inhibition MTT assay, with GI(50) values in the low nanomolar range for compound 1c. Significantly, compound le was found to have a GI(50) value of 2 nM in the paclitaxel resistant, p-glycoprotein overexpressed, MESSA/DX5 tumor cells. Functionally, compound 1c was found to be a potent inhibitor of tubulin polymerization and to effectively inhibit the binding of colchicine to tubulin. These results confirm that the cell-based caspase activation assay is a powerful tool for the discovery of potent apoptosis inducers and suggest that the 4-aryl-4H-chromenes have the potential to be developed into future anticancer agents.
• US6906203B1
  申请人：——

  公开号：US6906203B1

  公开（公告）日：2005-06-14