benzyl N-[1-(3,3-dimethyl-2-oxobutyl)-2-oxo-5-(1,3-thiazol-2-yl)-3H-1,4-benzodiazepin-3-yl]carbamate | 168161-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: benzyl N-[1-(3,3-dimethyl-2-oxobutyl)-2-oxo-5-(1,3-thiazol-2-yl)-3H-1,4-benzodiazepin-3-yl]carbamate
• CAS: 168161-79-3
• 化学式: C₂₆H₂₆N₄O₄S
• 分子量: 490.583
• InChiKey: MULVIGNQEVDHFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl N-[1-(3,3-dimethyl-2-oxobutyl)-2-oxo-5-(1,3-thiazol-2-yl)-3H-1,4-benzodiazepin-3-yl]carbamate 在 palladium on activated charcoal 氢气 作用下， 生成 2H-1,4-苯并二氮卓-2-酮,3-氨基-1-(3,3-二甲基-2-羰基丁基)-1,3-二氢-5-(2-噻唑基)-
  参考文献：
  名称：

  Synthesis and biological activity of 5-heteroaryl benzodiazepines: analogues of YM022

  摘要：

  A novel series of analogues of the potent gastrin/CCK-B receptor antagonist YM022 have been prepared which incorporate 5- and 6-membered heteroaromatic rings in the benzodiazepine 5-position. The 5-(2-pyridyl) derivatives in particular retained good in vitro and in vivo potency and one such compound 9i was shown to inhibit acid secretion after oral dosing in dogs. improved bioavailability for 9i over the 5-phenyl analogue, 9h was demonstrated in rats.

  DOI：

  10.1016/0960-894x(95)00557-a
• 作为产物：
  描述：

  2-aminophenyl-2'-thiazolylketone 在 氨 、 sodium hydride 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 为溶剂， 生成 benzyl N-[1-(3,3-dimethyl-2-oxobutyl)-2-oxo-5-(1,3-thiazol-2-yl)-3H-1,4-benzodiazepin-3-yl]carbamate
  参考文献：
  名称：

  Synthesis and biological activity of 5-heteroaryl benzodiazepines: analogues of YM022

  摘要：

  A novel series of analogues of the potent gastrin/CCK-B receptor antagonist YM022 have been prepared which incorporate 5- and 6-membered heteroaromatic rings in the benzodiazepine 5-position. The 5-(2-pyridyl) derivatives in particular retained good in vitro and in vivo potency and one such compound 9i was shown to inhibit acid secretion after oral dosing in dogs. improved bioavailability for 9i over the 5-phenyl analogue, 9h was demonstrated in rats.

  DOI：

  10.1016/0960-894x(95)00557-a

文献信息

• [EN] BENZODIAZEPINE COMPOUNDS USEFUL AS ANTAGONISTS OF CCK OR OF GASTRINE<br/>[FR] COMPOSES DE BENZODIAZEPINE UTILISES COMME ANTAGONISTES DE LA CCK OU DE LA GASTRINE
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：WO1995006040A1

  公开（公告）日：1995-03-02

  (EN) A benzodiazepine derivative of formula (I), or a pharmaceutically acceptable salt thereof, wherein: (a) R4 is an alkyl, cycloalkyl or aryl group; (b) R10 is chosen from halo, OH, CH3, OCH3, NR11R12, NO2, NHCHO, CO2H and CN, and R11 and R12 are independently selected from H and alkyl (C1-C5) or together NR11R12 form a cyclic structure (II), wherein a is 1-6; and (c) R2 is an aromatic 5- or 6-membered, substituted or unsubstituted heterocycle containing at least two heteroatoms of which at least one is nitrogen. These compounds are gastrin and/or CCK-B receptor antagonists.(FR) Dérivé de benzodiazépine de la formule (I), ou sel pharmaceutiquement acceptable de celui-ci. Dans la formule, (a) R4 représente un groupe alcoyle, cycloalcoyle ou aryle; (b) R10 est sélectionné parmi halo, OH, CH3, OCH3, NR11R12, NO2; NHCHO, CO2H et CN, et R11 et R12 sont sélectionnés indépendamment entre H et alcoyle (C1-C5) ou NR11R12 ensemble forment une structure cyclique (II), où a est compris entre 1 et 6; et (c) R2 représente un hétérocycle aromatique à 5 ou 6 éléments, avec ou sans substitution, qui contient au moins deux hétéroatomes dont l'un au moins est un atome d'azote. Ces composés sont des antagonistes des récepteurs de la gastrine et/ou de la CCK-B.

  一种公式（I）的苯二氮平衍生物，或其药学上可接受的盐，其中：（a）R4是烷基，环烷基或芳基；（b）R10选择自卤，OH，CH3，OCH3，NR11R12，NO2，NHCHO，CO2H和CN，其中R11和R12独立地选择自H和烷基（C1-C5），或者一起NR11R12形成一个环状结构（II），其中a为1-6；（c）R2是含有至少两个杂原子的芳香5-或6-成员替代或未替代杂环，其中至少一个是氮原子。这些化合物是胃泌素和/或CCK-B受体拮抗剂。
• BENZODIAZEPINE COMPOUNDS USEFUL AS ANTAGONISTS OF CCK OR OF GASTRINE
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0715624A1

  公开（公告）日：1996-06-12
• PROCESS FOR THE PREPARATION OF BENZODIAZEPINE COMPOUNDS USEFUL AS ANTAGONISTS OF CCK OR OF GASTRINE
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0715624B1

  公开（公告）日：1998-04-08
• US5728829A
  申请人：——

  公开号：US5728829A

  公开（公告）日：1998-03-17
• Synthesis and biological activity of 5-heteroaryl benzodiazepines: analogues of YM022
  作者：Graeme Semple、Hamish Ryder、David A. Kendrick、Michael Szelke、Mitsuaki Ohta、Masato Satoh、Akito Nishida、Shinobu Akuzawa、Keiji Miyata

  DOI：10.1016/0960-894x(95)00557-a

  日期：1996.1

  A novel series of analogues of the potent gastrin/CCK-B receptor antagonist YM022 have been prepared which incorporate 5- and 6-membered heteroaromatic rings in the benzodiazepine 5-position. The 5-(2-pyridyl) derivatives in particular retained good in vitro and in vivo potency and one such compound 9i was shown to inhibit acid secretion after oral dosing in dogs. improved bioavailability for 9i over the 5-phenyl analogue, 9h was demonstrated in rats.