rel-(3S,5S)-7-Chloro-5-cyclopropylethynyl-1,5-dihydro-3-propyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: rel-(3S,5S)-7-Chloro-5-cyclopropylethynyl-1,5-dihydro-3-propyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one
• 英文别名: (3S,5S)-7-chloro-5-(2-cyclopropylethynyl)-3-propyl-5-(trifluoromethyl)-1H-4,1-benzoxazepin-2-one
• 化学式: C₁₈H₁₇ClF₃NO₂
• 分子量: 371.787
• InChiKey: UZNAQYSRJBUJQZ-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(triphenylmethyl)-4-chloro-2-(trifluoroacetyl)aniline 在 吡啶 、 盐酸 、 正丁基锂 、 cerium (III) carbonate 、 lithium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.75h， 生成 rel-(3S,5S)-7-Chloro-5-cyclopropylethynyl-1,5-dihydro-3-propyl-5-(trifluoromethyl)-4,1-benzoxazepin-2(3H)-one
  参考文献：
  名称：

  4,1-Benzoxazepinone analogues of efavirenz (Sustiva™) as HIV-1 reverse transcriptase inhibitors

  摘要：

  A series of 4,1-benzoxazepinone analogues of efavirenz (Sustiva(TM)) as potent NNRTIs has been discovered. The cis-3-alkylbenzoxazepinones are more potent then the trans isomers and can be synthesized preferentially by a novel stereoselective cyclization. The best compounds are potent orally bioavailable inhibitors of both wild-type HIV-1 and its clinically relevant K103N mutant virus, but are highly protein-bound in human plasma. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00239-6

文献信息

• COMPOSITIONS AND METHODS FOR TREATMENT OF FILOVIRUS-MEDIATED DISEASES
  申请人：Johansen Lisa M.

  公开号：US20110028564A1

  公开（公告）日：2011-02-03

  The invention features compositions, methods, and kits useful for the treatment of filovirus-mediated diseases, e.g., hemorrhagic fever caused by Ebola virus, in an animal.
• US6140320A
  申请人：——

  公开号：US6140320A

  公开（公告）日：2000-10-31
• US6489320B1
  申请人：——

  公开号：US6489320B1

  公开（公告）日：2002-12-03
• US8475804B2
  申请人：——

  公开号：US8475804B2

  公开（公告）日：2013-07-02
• 4,1-Benzoxazepinone analogues of efavirenz (Sustiva™) as HIV-1 reverse transcriptase inhibitors
  作者：Anthony J. Cocuzza、Dennis R. Chidester、Beverly C. Cordova、Ronald M. Klabe、Susan Jeffrey、Sharon Diamond、Carolyn A. Weigelt、Soo S. Ko、Lee T. Bacheler、Susan K. Erickson-Viitanen、James D. Rodgers

  DOI：10.1016/s0960-894x(01)00239-6

  日期：2001.6

  A series of 4,1-benzoxazepinone analogues of efavirenz (Sustiva(TM)) as potent NNRTIs has been discovered. The cis-3-alkylbenzoxazepinones are more potent then the trans isomers and can be synthesized preferentially by a novel stereoselective cyclization. The best compounds are potent orally bioavailable inhibitors of both wild-type HIV-1 and its clinically relevant K103N mutant virus, but are highly protein-bound in human plasma. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.