(S)-4-(acetylthio)-2-(benzyloxycarbonylamino)butanoic acid | 167305-82-0

• 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)-4-(acetylthio)-2-(benzyloxycarbonylamino)butanoic acid
• 英文别名: S-Acetyl-N-[(phenylmethoxy)carbonyl]-L-homocysteine；(2S)-4-acetylsulfanyl-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 167305-82-0
• 化学式: C₁₄H₁₇NO₅S
• 分子量: 311.359
• InChiKey: KAAXPHOPIMAZFX-LBPRGKRZSA-N

物化性质

• 沸点：
  523.6±50.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-(acetylthio)-2-(benzyloxycarbonylamino)butanoic acid 在 N-甲基吗啉 、 甲醇 、 草酰氯 、 sodium methylate 、 1-羟基苯并三唑 、 二甲基亚砜 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 39.67h， 生成 (3S,7S,11S)-1-aza-3-benzyloxycarbonylamino-11-methoxycarbonyl-2-oxo-6-thiabicyclo[5.4.0]undecane
  参考文献：
  名称：

  Dual Metalloprotease Inhibitors:  Mercaptoacetyl-Based Fused Heterocyclic Dipeptide Mimetics as Inhibitors of Angiotensin-Converting Enzyme and Neutral Endopeptidase

  摘要：

  A series of 7,6- and 7,5-fused bicyclic thiazepinones and oxazepinones were generated and incorporated as conformationally restricted dipeptide surrogates in mercaptoacyl dipeptides. These compounds are potent inhibitors of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP) both in vitro and in vivo. Compound 1a, a 7,6-fused bicyclic thiazepinone, demonstrated excellent blood pressure lowering in a variety of animal models characterized by various levels of plasma renin activity and significantly potentiated urinary sodium, ANP, and cGMP excretion in a cynomolgus monkey assay. On the basis of its potency and duration of action, compound 1a (BMS-186716) was advanced into clinical development for the treatment of hypertension and congestive heart failure.

  DOI：

  10.1021/jm970041e
• 作为产物：
  描述：

  N-Benzyloxycarbonyl-D,L-homocystein-thiolacton 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 (S)-4-(acetylthio)-2-(benzyloxycarbonylamino)butanoic acid
  参考文献：
  名称：

  Dual Metalloprotease Inhibitors:  Mercaptoacetyl-Based Fused Heterocyclic Dipeptide Mimetics as Inhibitors of Angiotensin-Converting Enzyme and Neutral Endopeptidase

  摘要：

  A series of 7,6- and 7,5-fused bicyclic thiazepinones and oxazepinones were generated and incorporated as conformationally restricted dipeptide surrogates in mercaptoacyl dipeptides. These compounds are potent inhibitors of angiotensin-converting enzyme (ACE) and neutral endopeptidase (NEP) both in vitro and in vivo. Compound 1a, a 7,6-fused bicyclic thiazepinone, demonstrated excellent blood pressure lowering in a variety of animal models characterized by various levels of plasma renin activity and significantly potentiated urinary sodium, ANP, and cGMP excretion in a cynomolgus monkey assay. On the basis of its potency and duration of action, compound 1a (BMS-186716) was advanced into clinical development for the treatment of hypertension and congestive heart failure.

  DOI：

  10.1021/jm970041e
• 作为试剂：
  描述：

  (S)-4-(acetylthio)-2-(benzyloxycarbonylamino)butanoic acid 、 (S)-2-amino-6-hydroxy-hexanoic acid methyl ester 在 (S)-4-(acetylthio)-2-(benzyloxycarbonylamino)butanoic acid 作用下， 以88的产率得到methyl (2S)-2-[[(2S)-4-acetylsulfanyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]-6-hydroxyhexanoate
  参考文献：
  名称：

  Drugs of the Future 1999, 24, 269-277

  摘要：

  DOI：

文献信息

• [EN] SUBSTITUTED ADIPIC ACID AMIDES AND USES THEREOF<br/>[FR] AMIDES DE L'ACIDE ADIPIQUE SUBSTITUÉS ET LEURS UTILISATIONS
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012125622A1

  公开（公告）日：2012-09-20

  The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, wherein A is a five to eight membered monocyclic or a nine to twelve membered bicyclic heterocyclic ring, as further defined herein; Y is S, CH2, or CH; Z is CH or N; R7 and R9 are hydrogen or (C1-C6)alkyl; R2 is (C1 C6)alkoxy, OH, CN, (C1-C6)alkyl, halogen, or CF3; r and s are 0, 1, or 2; and R1 and R3 are as further defined herein. These compounds are agonists, partial agonists and/or modulators of the NPY4 receptor and may be used for the treatment and prophylaxis of obesity, food intake, and other diseases and conditions modulated by the NPY4 receptor.

  本发明提供了式（I）的化合物或其药学上可接受的盐，其中A是一个五至八元的单环或一个九至十二元的双环杂环环，如本文所进一步定义；Y是S、CH2或CH；Z是CH或N；R7和R9是氢或（C1-C6）烷基；R2是（C1-C6）烷氧基、羟基、氰基、（C1-C6）烷基、卤素或三氟甲基；r和s为0、1或2；R1和R3如本文所进一步定义。这些化合物是NPY4受体的激动剂、部分激动剂和/或调节剂，可用于治疗和预防肥胖、食物摄入和其他由NPY4受体调节的疾病和症状。
• DRUG THERAPY FOR CELIAC SPRUE
  申请人：KHOSLA CHAITAN

  公开号：US20090312260A1

  公开（公告）日：2009-12-17

  Administering an effective dose of a tTGase inhibitor to a Celiac or dermatitis herpetiformis patient reduces the toxic effects of toxic gluten oligopeptides, thereby attenuating or eliminating the damaging effects of gluten.

  给予具有有效剂量的tTGase抑制剂给予具有乳糜泻或疱疹性荨麻疹的患者，可以减少有毒的麸质寡肽的毒性影响，从而减轻或消除麸质的有害影响。
• SUBSTITUTED ADIPIC ACID AMIDES AND USES THEREOF
  申请人：Sun Chongqing

  公开号：US20130345123A1

  公开（公告）日：2013-12-26

  The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, wherein A is a five to eight membered monocyclic or a nine to twelve membered bicyclic heterocyclic ring, as further defined herein; Y is S, CH 2 , or CH; Z is CH or N; R 7 and R 9 are hydrogen or (C 1 -C 6 )alkyl; R 2 is (C 1 -C 6 )alkoxy, OH, CN, (C 1 -C 6 )alkyl, halogen, or CF 3 ; r and s are 0, 1, or 2; and R 1 and R 3 are as further defined herein. These compounds are agonists, partial agonists and/or modulators of the NPY4 receptor and may be used for the treatment and prophylaxis of obesity, food intake, and other diseases and conditions modulated by the NPY4 receptor.

  本发明提供了式（I）的化合物或其药学上可接受的盐，其中A是进一步定义的五至八元杂环或九至十二元双环杂环；Y是S，CH2或CH；Z是CH或N；R7和R9是氢或（C1-C6）烷基；R2是（C1-C6）烷氧基，羟基，氰基，（C1-C6）烷基，卤素或CF3；r和s为0、1或2；而R1和R3的定义进一步如下。这些化合物是NPY4受体的激动剂、部分激动剂和/或调节剂，可用于治疗和预防肥胖、食物摄入和其他受NPY4受体调节的疾病和状况。
• Substituted adipic acid amides and uses thereof
  申请人：Sun Chongqing

  公开号：US09346852B2

  公开（公告）日：2016-05-24

  The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, wherein A is a five to eight membered monocyclic or a nine to twelve membered bicyclic heterocyclic ring, as further defined herein; Y is S, CH2, or CH; Z is CH or N; R7 and R9 are hydrogen or (C1-C6)alkyl; R2 is (C1-C6)alkoxy, OH, CN, (C1-C6)alkyl, halogen, or CF3; r and s are 0, 1, or 2; and R1 and R3 are as further defined herein. These compounds are agonists, partial agonists and/or modulators of the NPY4 receptor and may be used for the treatment and prophylaxis of obesity, food intake, and other diseases and conditions modulated by the NPY4 receptor.

  本发明提供了公式（I）的化合物或其药学上可接受的盐，其中A是进一步定义的五至八元的单环或九至十二元的双环杂环环，Y是S，CH2或CH; Z是CH或N; R7和R9是氢或（C1-C6）烷基; R2是（C1-C6）烷氧基，羟基，氰基，（C1-C6）烷基，卤素或CF3; r和s为0,1或2; R1和R3如进一步定义。这些化合物是NPY4受体的激动剂，部分激动剂和/或调节剂，可用于治疗和预防肥胖，食物摄入和其他受NPY4受体调节的疾病和状况。
• Benzo-fused azepinone and piperidinone compounds useful in the inhibition of ace and nep
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0743319A1

  公开（公告）日：1996-11-20

  Compounds having the following formula I, and pharmaceutically acceptable salts thereof, including dual inhibitors of ACE and NEP and selective ACE inhibitors: wherein: Y1 and Y2 are each independently hydrogen, alkyl, aryl, halogen, or alkoxy; X is O or S(O)t; A is t is zero, one or two; m and n are independently zero or one; and wherein R, R5, R5a, R5b, R6, R7, R11, q and r are defined herein.

  具有下式 I 的化合物及其药学上可接受的盐类，包括 ACE 和 NEP 双抑制剂以及选择性 ACE 抑制剂： 其中 Y1 和 Y2 各自独立地为氢、烷基、芳基、卤素或烷氧基； X 是 O 或 S(O)t； A 是 t 为 0、1 或 2 m 和 n 独立地为零或一个； 其中 R、R5、R5a、R5b、R6、R7、R11、q 和 r 在本文中定义。