S-2-溴戊酸 | 32835-74-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: S-2-溴戊酸
• 英文名称: (S)-α-Brom-valeriansaeure
• 英文别名: (S)-2-bromovaleric acid；(S)-2-Brom-valeriansaeure；L(-)-2-Brom-valeriansaeure；(2S)-2-bromopentanoic acid
• CAS: 32835-74-8
• 化学式: C₅H₉BrO₂
• 分子量: 181.029
• InChiKey: WMFATTFQNRPXBQ-BYPYZUCNSA-N

物化性质

• 沸点：
  232.2±13.0 °C(Predicted)
• 密度：
  1.518±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2915900090

反应信息

• 作为产物：
  描述：

  L-正缬氨酸 在 硫酸 、 potassium bromide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 5.0h， 生成 S-2-溴戊酸
  参考文献：
  名称：

  Discovery of a Peroxisome Proliferator Activated Receptor γ (PPARγ) Modulator with Balanced PPARα Activity for the Treatment of Type 2 Diabetes and Dyslipidemia

  摘要：

  A series of 3-acylindole-1-benzylcarboxylic acids were designed and synthesized while searching for a PPAR gamma modulator with additional moderate intrinsic PPAR alpha agonistic activity. 2-[3-[[3-(4-Chlorobenzoyl)-2-methyl-6-(trifluoromethoxy)-1H-indol-1-yl]methyl]phenoxy]-(2R)-butanoic acid (12d) was identified as such an agent which demonstrated potent efficacy in lowering both glucose and lipids in multiple animal models with significantly attenuated side effects such as fluid retention and heart weight gain associated with PPAR gamma full agonists, The moderate PPAR alpha activity of 12d not only contributed to the agent's ability to manage lipid profiles but also appears to have potentiated its PPAR gamma efficacy in lowering glucose levels in preclinical diabetic animal models.

  DOI：

  10.1021/jm900367w

文献信息

• Asymmetric Synthesis of 2-chloro- and 2-bromo-alkanoic acids by halogenation of α-D-glucofuranose-derived silyl ketene acetals
  作者：P Angibaud、J.L Chaumette、J.R Desmurs、L Duhamel、G Plé、J.Y Valnot、P Duhamel

  DOI：10.1016/0957-4166(95)00251-j

  日期：1995.8

  2-chloro-alkanoic acids 6 and 7 have been obtained the diastereoselective halogenation of chiral silyl ketene acetals 3a-f, and subsequent saponification of the resulting crude esters. Examples characterized by e.e. values up to 95% are reported. The diastereoface selectivity is independent of the silyl ketene acetal configuration.

  光学活性的（S）-2-溴-和2-氯-链烷酸6和7已经获得了手性甲硅烷基烯酮缩醛3a-f的非对映选择性卤化，随后将所得的粗酯皂化。报告了以ee值高达95％为特征的示例。非对映体的选择性与甲硅烷基烯酮缩醛构型无关。
• Design and synthesis of potent thiol-based inhibitors of endothelin converting enzyme-1
  作者：Cynthia A Fink、Michael Moskal、Fariborz Firooznia、Denton Hoyer、David Symonsbergen、Dongchu Wei、Ying Qiao、Paula Savage、Michael E Beil、Angelo J Trapani、Arco Y Jeng

  DOI：10.1016/s0960-894x(00)00403-0

  日期：2000.9

  Through directed screening of compounds prepared as metalloprotease inhibitors a compound, CGS 30084, that had potent endothelin converting enzyme-1 (ECE-1) in vitro inhibitory activity (IC50 = 77 nM) was identified. Herein we report the synthesis and optimization of ECE-1 inhibitory activity of additional analogues from this lead. Compound 3c, the thioacetate methyl ester derivative of compound 4c, was found to be a long acting inhibitor of ECE-1 activity in rats after oral administration. (C) 2000 Elsevier Science Ltd. All rights reserved.