[3-tert-Butoxycarbonylamino-9-chloro-5-(2-fluoro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetic acid ethyl ester | 205991-83-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [3-tert-Butoxycarbonylamino-9-chloro-5-(2-fluoro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetic acid ethyl ester
• 英文别名: ethyl 2-[9-chloro-5-(2-fluorophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-oxo-3H-1,4-benzodiazepin-1-yl]acetate
• CAS: 205991-83-9
• 化学式: C₂₄H₂₅ClFN₃O₅
• 分子量: 489.931
• InChiKey: YURZHYYNTMSTRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [3-tert-Butoxycarbonylamino-9-chloro-5-(2-fluoro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetic acid ethyl ester 在 盐酸 、 sodium hydroxide 、 WSCD*HCl 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(3RS)-1-(3-Azabicyclo[3.2.2]non-3-yl)carbonylmethyl-9-chloro-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-[3-(tetrazol-5-yl)phenyl]urea
  参考文献：
  名称：

  Relationship between dihedral angles of N1 and C9 substituents in 1,4-benzodiazepines and dual cholecystokinin-A and -B antagonistic activities

  摘要：

  Introduction of a methyl moiety to the C9 position of a 1,4-benzodiazepine ring system afforded dual CCK-A and -B antagonistic activity. Novel derivatives having ethyl, isopropyl and chloro substituents at C9 were prepared in order to obtain more potent antagonistic activities. AM1(MOPAC93) calculations of the dihedral angles between the N1 and C9 substituents indicated that dihedral angles for dual antagonistic activities were between 50 degrees and 60 degrees. A methyl moiety was selected as the most suitable C9 substituent in this series for potent dual CCK-A and -B receptor antagonistic properties. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00237-6
• 作为产物：
  描述：

  3-Amino-9-chloro-5-(2-fluoro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one 在 盐酸羟胺 、 sodium hydride 、 三乙胺 作用下， 生成 [3-tert-Butoxycarbonylamino-9-chloro-5-(2-fluoro-phenyl)-2-oxo-2,3-dihydro-benzo[e][1,4]diazepin-1-yl]-acetic acid ethyl ester
  参考文献：
  名称：

  Relationship between dihedral angles of N1 and C9 substituents in 1,4-benzodiazepines and dual cholecystokinin-A and -B antagonistic activities

  摘要：

  Introduction of a methyl moiety to the C9 position of a 1,4-benzodiazepine ring system afforded dual CCK-A and -B antagonistic activity. Novel derivatives having ethyl, isopropyl and chloro substituents at C9 were prepared in order to obtain more potent antagonistic activities. AM1(MOPAC93) calculations of the dihedral angles between the N1 and C9 substituents indicated that dihedral angles for dual antagonistic activities were between 50 degrees and 60 degrees. A methyl moiety was selected as the most suitable C9 substituent in this series for potent dual CCK-A and -B receptor antagonistic properties. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00237-6

文献信息

• 1,4-benzodiazepinones and their uses as CCK antagonists
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US20020183313A1

  公开（公告）日：2002-12-05

  Benzodiazepine derivatives of the formula: 1 wherein R 1 is heterocyclic(lower)alkyl which may have one or more suitable substituent(s), etc., R 2 is lower alkyl, etc., R 3 is indolyl, etc., R 4 is hydrogen, etc., or a pharmaceutically acceptable salt thereof, which are useful as a medicament.

  公式为1的苯二氮平衍生物，其中R1为杂环（较低）烷基，可以有一个或多个合适的取代基等，R2为较低的烷基等，R3为吲哚基等，R4为氢等，或其药学上可接受的盐，可用作药物。
• 1,4-BENZODIAZEPINONES AND THEIR USES AS CCK ANTAGONISTS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0934282A1

  公开（公告）日：1999-08-11
• US6291452B1
  申请人：——

  公开号：US6291452B1

  公开（公告）日：2001-09-18
• [EN] 1,4-BENZODIAZEPINONES AND THEIR USES AS CCK ANTAGONISTS<br/>[FR] 1,4-BENZODIAZEPINONES ET LEURS UTILISATIONS EN TANT QU'ANTAGONISTES DE CCK
  申请人：——

  公开号：WO1998015535A1

  公开（公告）日：1998-04-16

  [EN] Benzodiazepine derivatives of formula (I) wherein R<2> is alkyl or cycloalkyl-alkyl when R<4> is hydrogen, or R<2> is a variety of specified groups when R<4> is alkyl, halogen or dialkylamino, are useful as cholecystokinin antagonists.
  [FR] L'invention concerne des dérivés de benzodiazépine de formule (I), qui sont utiles en tant qu'antogonistes de la cholécystokinine. Dans la formule (I), R<2> représente alkyle ou cycloalkyle-alkyle lorsque R<4> représente hydrogène, ou R<2> représente divers groupes spécifiés lorsque R<4> représente alkyle, halogène ou dialkylamino.
• Relationship between dihedral angles of N1 and C9 substituents in 1,4-benzodiazepines and dual cholecystokinin-A and -B antagonistic activities
  作者：Seiichiro Tabuchi、Isao Nakanishi、Yoshinari Satoh

  DOI：10.1016/s0960-894x(98)00237-6

  日期：1998.6

  Introduction of a methyl moiety to the C9 position of a 1,4-benzodiazepine ring system afforded dual CCK-A and -B antagonistic activity. Novel derivatives having ethyl, isopropyl and chloro substituents at C9 were prepared in order to obtain more potent antagonistic activities. AM1(MOPAC93) calculations of the dihedral angles between the N1 and C9 substituents indicated that dihedral angles for dual antagonistic activities were between 50 degrees and 60 degrees. A methyl moiety was selected as the most suitable C9 substituent in this series for potent dual CCK-A and -B receptor antagonistic properties. (C) 1998 Elsevier Science Ltd. All rights reserved.