S-(o-nitrophenyl)-N-(carbobenzyloxy)-L-cysteine | 94590-53-1

• 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: S-(o-nitrophenyl)-N-(carbobenzyloxy)-L-cysteine
• 英文别名: S-(o-nitrophenyl)-N-carbobenzyloxy-L-cysteine；(2R)-3-(2-nitrophenyl)sulfanyl-2-(phenylmethoxycarbonylamino)propanoic acid
• CAS: 94590-53-1
• 化学式: C₁₇H₁₆N₂O₆S
• 分子量: 376.39
• InChiKey: CATWNVKPCIXCIZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  S-(o-nitrophenyl)-N-(carbobenzyloxy)-L-cysteine 在 氢溴酸 、 氯化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 锌 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (3R)-3-Amino-2,3-dihydro-1,5-benzothiazepin-4(5H)-on
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors: 1,5-benzothiazepine derivatives

  摘要：

  The synthesis of chiral 1,5-benzothiazepines 2a-c, 14a-c, 15c, and 16a prepared from cysteine is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound. Compound 2c was the most potent in vitro having an IC50 of 2.95 nM. The ester of 2c, i.e. 14c, was found to inhibit the AI pressor response by 75% at a dose of 0.05 mg/kg iv and by 39% at 1.0 mg/kg po. Additionally, 14c lowered blood pressure in the spontaneous hypertensive rat (SHR) by 35 mmHg, at a dose of 10 mg/kg po.

  DOI：

  10.1021/jm00148a024
• 作为产物：
  描述：

  N-acetyl-S-(2-nitro-phenyl)-L-cysteine 在 sodium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 S-(o-nitrophenyl)-N-(carbobenzyloxy)-L-cysteine
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors: 1,5-benzothiazepine derivatives

  摘要：

  The synthesis of chiral 1,5-benzothiazepines 2a-c, 14a-c, 15c, and 16a prepared from cysteine is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound. Compound 2c was the most potent in vitro having an IC50 of 2.95 nM. The ester of 2c, i.e. 14c, was found to inhibit the AI pressor response by 75% at a dose of 0.05 mg/kg iv and by 39% at 1.0 mg/kg po. Additionally, 14c lowered blood pressure in the spontaneous hypertensive rat (SHR) by 35 mmHg, at a dose of 10 mg/kg po.

  DOI：

  10.1021/jm00148a024

文献信息

• Hetero-benzazepine derivatives and their pharmaceutical use
  申请人：Ciba-Geigy Corporation

  公开号：US04477464A1

  公开（公告）日：1984-10-16

  Disclosed are variously substituted 3-(carboxymethylamino)-(1,5-benzothiazepin-4-one, 1,5-benzoxazepin-4-one and 1,5-benzodiazepin-4-one)-5-alkanoic acids and derivatives as angiotensin-converting enzyme inhibitors and antihypertensive agents. Their synthesis, pharmaceutical compositions thereof, and methods of threatment utilizing such compounds are included.

  本发明涉及多种取代的3-(羧甲基氨基)-(1,5-苯并噻吩-4-酮，1,5-苯并噁唑-4-酮和1,5-苯并二氮杂-4-酮)-5-脂肪酸类化合物及其衍生物，作为血管紧张素转化酶抑制剂和降压药物。本发明还包括这些化合物的合成方法，药物组成物以及利用这些化合物进行治疗的方法。
• US4477464A
  申请人：——

  公开号：US4477464A

  公开（公告）日：1984-10-16
• [EN] THIOAZEPINONE DERIVATIVES, PREPARATION METHOD AND INTERMEDIATES THEREFOR, USE AS MEDICINES AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME<br/>[FR] DERIVES DE THIOAZEPINONE, PROCEDE DE PREPARATION ET INTERMEDIAIRES DE CE PROCEDE, APPLICATION COMME MEDICAMENTS ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：HOECHST MARION ROUSSEL INC

  公开号：WO2000005246A1

  公开（公告）日：2000-02-03

  L'invention a pour objet un dérivé de thioazepinone de formule (I) dans laquelle R1, R2, R3, R4, R5, X, [A1], A2 et U ont les significations indiquées dans la description, leurs sels et leurs promédicaments. L'invention de plus a pour objet les procédés de préparation des composés de formule (I), les intermédiaires de ce procédé, leur application à titre de médicaments, notamment comme inhibiteurs du domaine Src SH2 et inhibiteurs de la résorption osseuse médiée par les ostéoclastes, et les compositions pharmaceutiques les renfermant.
• Angiotensin converting enzyme inhibitors: 1,5-benzothiazepine derivatives
  作者：Joel Slade、James L. Stanton、Daniel Ben-David、Gerard C. Mazzenga

  DOI：10.1021/jm00148a024

  日期：1985.10

  The synthesis of chiral 1,5-benzothiazepines 2a-c, 14a-c, 15c, and 16a prepared from cysteine is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound. Compound 2c was the most potent in vitro having an IC50 of 2.95 nM. The ester of 2c, i.e. 14c, was found to inhibit the AI pressor response by 75% at a dose of 0.05 mg/kg iv and by 39% at 1.0 mg/kg po. Additionally, 14c lowered blood pressure in the spontaneous hypertensive rat (SHR) by 35 mmHg, at a dose of 10 mg/kg po.