5-((pentoxysuccinyl)amino)-2-(benzylthio)-1,3,4-thiadiazole | 129504-23-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-((pentoxysuccinyl)amino)-2-(benzylthio)-1,3,4-thiadiazole
• 英文别名: pentyl 4-[(5-benzylsulfanyl-1,3,4-thiadiazol-2-yl)amino]-4-oxobutanoate
• CAS: 129504-23-0
• 化学式: C₁₈H₂₃N₃O₃S₂
• 分子量: 393.531
• InChiKey: ZQYCPPQXQVPVDC-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  81.18
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-((pentoxysuccinyl)amino)-2-(benzylthio)-1,3,4-thiadiazole 在 氯 、 溶剂黄146 作用下， 反应 4.0h， 生成 5-<(pentoxysuccinyl)amino>-1,3,4-thiadiazole-2-sulfonyl chloride
  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
• 作为产物：
  描述：

  氨基苄巯基噻二唑 、 succinyl chloride monopentyl 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60%的产率得到5-((pentoxysuccinyl)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