succinyl chloride sec-butyl ester | 140697-04-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: succinyl chloride sec-butyl ester
• 英文别名: Butan-2-yl 4-chloro-4-oxobutanoate
• CAS: 140697-04-7
• 化学式: C₈H₁₃ClO₃
• 分子量: 192.642
• InChiKey: XGZKKWYIXMZYDX-UHFFFAOYSA-N

物化性质

• 沸点：
  239.6±23.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氨基苄巯基噻二唑 、 succinyl chloride sec-butyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以50%的产率得到5-((sec-butoxysuccinyl)amino)-2-(benzylthio)-1,3,4-thiadiazole
  参考文献：
  名称：

  Acetazolamide-like carbonic anhydrase inhibitors with topical ocular hypotensive activity

  摘要：

  New carbonic anhydrase (EC 4.2.1.1) inhibitors were synthesized as potential drugs for the topical treatment of glaucoma. They were obtained by substituting the acetyl group of acetazolamide and methazolamide with bicarboxylic acids of different chain length (C4-C6). The terminal carboxyl was either kept free or esterified with alcohols of different size (C1-C12). A gamma-aminovaleric derivative was also prepared. All compounds proved active as carbonic anhydrase inhibitors in vitro, with an average IC50 of about 0.5-mu-M. Some proved also to be topically active in vivo in lowering the artificially elevated intraocular pressure in rabbits. The most active compound, carrying a succinic acid side chain, is the most soluble in aqueous buffers. Its duration of action is about 8 h and it is under evaluation as a topical antiglaucoma drug. It is hypothesized that the duration of action could be longer in compounds having both the same high water solubility and partition coefficient.

  DOI：

  10.1021/jm00092a021

文献信息

• Acetazolamide-like carbonic anhydrase inhibitors with topical ocular hypotensive activity
  作者：Simonetta Antonaroli、Armandodoriano Bianco、Mario Brufani、Luciano Cellai、Giuseppe Lo Baido、Edoardo Potier、Luciano Bonomi、Sergio Perfetti、Anna Ida Fiaschi、Giorgio Segre

  DOI：10.1021/jm00092a021

  日期：1992.7

  New carbonic anhydrase (EC 4.2.1.1) inhibitors were synthesized as potential drugs for the topical treatment of glaucoma. They were obtained by substituting the acetyl group of acetazolamide and methazolamide with bicarboxylic acids of different chain length (C4-C6). The terminal carboxyl was either kept free or esterified with alcohols of different size (C1-C12). A gamma-aminovaleric derivative was also prepared. All compounds proved active as carbonic anhydrase inhibitors in vitro, with an average IC50 of about 0.5-mu-M. Some proved also to be topically active in vivo in lowering the artificially elevated intraocular pressure in rabbits. The most active compound, carrying a succinic acid side chain, is the most soluble in aqueous buffers. Its duration of action is about 8 h and it is under evaluation as a topical antiglaucoma drug. It is hypothesized that the duration of action could be longer in compounds having both the same high water solubility and partition coefficient.