(S)-2-Acetylsulfanyl-3-biphenyl-4-yl-propionic acid | 250266-12-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-Acetylsulfanyl-3-biphenyl-4-yl-propionic acid
• 英文别名: (2S)-2-acetylsulfanyl-3-(4-phenylphenyl)propanoic acid
• CAS: 250266-12-7
• 化学式: C₁₇H₁₆O₃S
• 分子量: 300.378
• InChiKey: DOIIMJAAMADLSI-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-Acetylsulfanyl-3-biphenyl-4-yl-propionic acid 在 lithium hydroxide 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,5S)-5-((S)-3-Biphenyl-4-yl-2-mercapto-propionylamino)-4-oxo-1,2,4,5,6,7-hexahydro-azepino[3,2,1-hi]indole-2-carboxylic acid
  参考文献：
  名称：

  Dual inhibition of angiotensin-converting enzyme and neutral endopeptidase by tricyclic benzazepinone thiols

  摘要：

  Various thioacyl analogs of CGS 28106, a tricyclic dual inhibitor of angiotensin-converting enzyme and neutral endopeptidase, have been synthesized and their inhibitory potencies evaluated in vitro. The structure-activity relationship supports the proposed hypothesis that, despite its conformational constraints, CGS 28106 can inhibit the two distinct metalloproteases by adopting different binding modes. Tn addition, the structural features of CGS 28106 confer remarkable oral activity to this dual inhibitor, as measured by its ability to block the angiotensin-I presser response and to potentiate plasma levels of atrial natriuretic peptide. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00529-x
• 作为产物：
  描述：

  3-(4-联苯基)丙酸 在 吡啶 、 4-二甲氨基吡啶 、 lithium hydroxide 、 草酰氯 、 双氧水 、 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-Acetylsulfanyl-3-biphenyl-4-yl-propionic acid
  参考文献：
  名称：

  Synthesis and SAR of thioester and thiol inhibitors of IMP-1 Metallo-β-Lactamase

  摘要：

  Potent thioester and thiol inhibitors of IMP-1 metallo-beta-lactamase have been synthesized employing a solid-phase Mitsunobu reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00425-4

文献信息

• Synthesis and SAR of thioester and thiol inhibitors of IMP-1 Metallo-β-Lactamase
  作者：Mark L. Greenlee、Joanne B. Laub、James M. Balkovec、Milton L. Hammond、Gail G. Hammond、David L. Pompliano、Jeffrey H. Epstein-Toney

  DOI：10.1016/s0960-894x(99)00425-4

  日期：1999.9

  Potent thioester and thiol inhibitors of IMP-1 metallo-beta-lactamase have been synthesized employing a solid-phase Mitsunobu reaction as the key step. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Dual inhibition of angiotensin-converting enzyme and neutral endopeptidase by tricyclic benzazepinone thiols
  作者：Stéphane De Lombaert、Louis Blanchard、Lisa B. Stamford、Yumi Sakane、Carol Berry、Rajendra D. Ghai、Angelo J. Trapani

  DOI：10.1016/s0960-894x(96)00529-x

  日期：1996.12

  Various thioacyl analogs of CGS 28106, a tricyclic dual inhibitor of angiotensin-converting enzyme and neutral endopeptidase, have been synthesized and their inhibitory potencies evaluated in vitro. The structure-activity relationship supports the proposed hypothesis that, despite its conformational constraints, CGS 28106 can inhibit the two distinct metalloproteases by adopting different binding modes. Tn addition, the structural features of CGS 28106 confer remarkable oral activity to this dual inhibitor, as measured by its ability to block the angiotensin-I presser response and to potentiate plasma levels of atrial natriuretic peptide. Copyright (C) 1996 Elsevier Science Ltd