5-((5-chlorovaleryl)amino)-2-(benzylthio)-1,3,4-thiadiazole | 140833-97-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-((5-chlorovaleryl)amino)-2-(benzylthio)-1,3,4-thiadiazole
• 英文别名: 5-chlorovaleroylamino-2-benzylmercapto-1,3,4-thiadiazole；N-(5-benzylsulfanyl-1,3,4-thiadiazol-2-yl)-5-chloropentanamide
• CAS: 140833-97-2
• 化学式: C₁₄H₁₆ClN₃OS₂
• 分子量: 341.886
• InChiKey: YNYHMWSSLNHRDV-UHFFFAOYSA-N

物化性质

• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-((5-chlorovaleryl)amino)-2-(benzylthio)-1,3,4-thiadiazole 在 氯 、 溶剂黄146 作用下， 反应 3.0h， 生成
  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 、 5-氯代戊酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到5-((5-chlorovaleryl)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-related compounds, process for their preparation, and
  申请人：Instituto Chimico Internazionale Dr. Giuseppe Rende S.r.l.

  公开号：US05010204A1

  公开（公告）日：1991-04-23

  Compounds related to acetazolamide and to its N-methyl derivatives, of the formulae: ##STR1## wherein Y is one of the following groups: ##STR2## R.sub.1 being a straight or branched alkylene or arylalkylene, or a phenylene, and the processes for their preparation; the compounds so obtained are inhibitors of carbonic anhydrase like acetazolamide but, in addition, they are well absorbed topically so that they can be used as drugs for treating glaucoma.

  与乙酰唑胺及其N-甲基衍生物相关的化合物，其化学式为：其中Y是以下组之一：R.sub.1是直链或支链烷基或芳基烷基，或苯基，以及它们的制备方法；所得的化合物是碳酸酐酶抑制剂，类似于乙酰唑胺，但另外，它们在局部吸收良好，因此可以用作治疗青光眼的药物。
• Acetazolamide-related compounds, process for their preparation, and pharmaceutical composition containing the same
  申请人：ISTITUTO CHIMICO INTERNAZIONALE DR. GIUSEPPE RENDE S.R.L.

  公开号：EP0354881B1

  公开（公告）日：1992-04-22
• US5010204A
  申请人：——

  公开号：US5010204A

  公开（公告）日：1991-04-23
• US5270338A
  申请人：——

  公开号：US5270338A

  公开（公告）日：1993-12-14
• 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.