3(R)-<(carbobenzyloxy)amino>-2,3-dihydro-1,5-benzothiazepin-4(5H)-one | 94590-55-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 3(R)-<(carbobenzyloxy)amino>-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
• 英文别名: ((R)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl)-carbamic acid benzyl ester；benzyl N-[(3R)-4-oxo-3,5-dihydro-2H-1,5-benzothiazepin-3-yl]carbamate
• CAS: 94590-55-3
• 化学式: C₁₇H₁₆N₂O₃S
• 分子量: 328.392
• InChiKey: IZBNQQLRKDDKSD-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3(R)-<(carbobenzyloxy)amino>-2,3-dihydro-1,5-benzothiazepin-4(5H)-one 在 氢溴酸 作用下， 反应 1.0h， 以68%的产率得到(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 、 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 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 3(R)-<(carbobenzyloxy)amino>-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
  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

• Substituted Benzodiazepinones, Benzoxazepinones and Benzothiazepinones as Sodium Channel Blockers
  申请人：Hoyt Scott B.

  公开号：US20100144715A1

  公开（公告）日：2010-06-10

  The present invention is directed to substituted benzodiazepinones, benzoxazepinones and benzothiazepinones compounds that are sodium channel blockers useful for the treatment of chronic and neuropathic pain. The compounds of the present invention are also useful for the treatment of other conditions, including disorders of the CNS such as anxiety, depression, epilepsy, manic depression and bipolar disorder. This invention also provides pharmaceutical compositions comprising a compound of the present invention, either alone, or in combination with one or more therapeutically active compounds, and a pharmaceutically acceptable carrier. This invention further comprises methods for the treatment of acute pain, chronic pain, visceral pain, inflammatory pain, neuropathic pain and disorders of the CNS including, but not limited to, epilepsy, manic depression, depression, anxiety and bipolar disorder comprising administering the compounds and pharmaceutical compositions of the present invention.

  本发明涉及替代苯二氮平酮、苯并噁唑酮和苯并噻唑酮化合物，它们是钠通道阻滞剂，可用于治疗慢性和神经病理性疼痛。本发明的化合物也可用于治疗其他疾病，包括中枢神经系统紊乱，如焦虑、抑郁、癫痫、躁郁症和双相障碍。本发明还提供了含有本发明化合物的药物组合物，可以单独使用或与一个或多个治疗活性化合物组合使用，并与药学上可接受的载体一起使用。本发明还包括治疗急性疼痛、慢性疼痛、内脏疼痛、炎症性疼痛、神经病理性疼痛和中枢神经系统紊乱的方法，包括但不限于癫痫、躁郁症、抑郁症、焦虑症和双相障碍，通过给予本发明的化合物和药物组合物进行治疗。
• Discovery of Thioazepinone Ligands for Src SH2: From Non-specific to Specific Binding
  作者：Dominique Lesuisse、Pierre Deprez、Eva Albert、Tran Thien Duc、Benoit Sortais、Dominique Gofflo、Véronique Jean-Baptiste、Jean-Pierre Marquette、Bernard Schoot、Edoardo Sarubbi、Gudrun Lange、Pierre Broto、Eliane Mandine

  DOI：10.1016/s0960-894x(01)00386-9

  日期：2001.8

  The structure-based design and synthesis of new thioazepinones as ligands for Src SH2 protein is presented. From benzothioazepinones, ligands with somewhat unspecific binding properties, simpler thioazepinones were designed, the best ones demonstrated nanomolar affinity for Src SH2. A few of these new ligands were crystallized with the protein and demonstrated a specific binding mode with the protein. (C) 2001 Elsevier Science Ltd. All rights reserved.
• WO2008/106077
  申请人：——

  公开号：——

  公开（公告）日：——
• SLADE, J.;STANTON, J. L.;BEN-DAVID, D.;MAZZENGA, G. C., J. MED. CHEM., 1985, N 10, 1517-1521
  作者：SLADE, J.、STANTON, J. L.、BEN-DAVID, D.、MAZZENGA, G. C.

  DOI：——

  日期：——
• SLADE, J.;STANTON, J. L.
  作者：SLADE, J.、STANTON, J. L.

  DOI：——

  日期：——