N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-benzamide | 55217-83-9

• 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: N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-benzamide
• 英文别名: N-(benzylmercapto-[1,3,4]thiadiazol-2-yl)-benzamide；N-(Benzylmercapto-[1,3,4]thiadiazol-2-yl)-benzamid；2-benzoylamino-5-benzyl-mercapto-1,3,4-thiadiazole；N-[5-(benzylsulfanyl)-1,3,4-thiadiazol-2-yl]benzamide；N-(5-benzylsulfanyl-1,3,4-thiadiazol-2-yl)benzamide
• CAS: 55217-83-9
• 化学式: C₁₆H₁₃N₃OS₂
• mdl: MFCD02032565
• 分子量: 327.431
• InChiKey: PVUYLUYGUIIBEU-UHFFFAOYSA-N

物化性质

• 熔点：
  190.5-192.5 °C(Solv: ethanol (64-17-5))
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-benzamide 在 水 、 氯 、 三氯化铁 作用下， 生成 benzoylamino-[1,3,4]thiadiazole-2-sulfonyl chloride
  参考文献：
  名称：

  Pala, Farmaco, Edizione Scientifica, 1958, vol. 13, p. 650,661

  摘要：

  DOI：
• 作为产物：
  描述：

  氨基苄巯基噻二唑 、 苯甲酰氯 以 水 为溶剂， 反应 0.5h， 以67%的产率得到N-(5-benzylsulfanyl-[1,3,4]thiadiazol-2-yl)-benzamide
  参考文献：
  名称：

  Synthesis of 2-Amino-5-sulfanyl-1,3,4-thiadiazole Derivatives and Evaluation of Their Antidepressant and Anxiolytic Activity

  摘要：

  Recently a series of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives bearing different substituents were synthesized and screened pharmacologically in order to evaluate their central nervous system activity. The purpose of this study was to evaluate the effects of the title compounds on CNS activity by varying the substituents in the thiadiazole moiety. It was found that some of these compounds possess marked antidepressant and anxiolytic properties comparable in efficiency to the reference drugs Imipramine and Diazepam. The most potent compound 3k was further investigated to complete its pharmacological profile with respect to undesired side effects. Behavioral results showed that 3k is a very promising compound, characterized by a mixed antidepressant-anxiolytic activity accompanied by a therapeutic dose range that is essentially 2 orders of magnitude less than that at which side effects such as sedation and amnesia are evident.

  DOI：

  10.1021/jm001027w

文献信息

• Substituted thiadiazolines as inhibitors of central nervous system carbonic anhydrase
  作者：James J. Lukes、Karl A. Nieforth

  DOI：10.1021/jm00238a005

  日期：1975.4

  A series (24-30) of substituted thiadiazolines was synthesized and tested for in vitro carbonic anhydrase inhibition and for protective ability against pentylenetetrazole-induced convulsions. ED50 (pentylenetetrazole protection), TD50, and LD50 values are reported for each compound. With the exception of 30, all compounds approximated the model compound methazolamide as in vitro carbonic anhydrase inhibitors. Several of the compounds produced extended protection against pentylenetetrazole-induced convulsions. Ring methoxy substitution in the ortho position appeared to produce maximum activity.
• Thiadiazole derivatives for the treatment of depressive states
  申请人：LABORATORIO FARMACEUTICO C.T. S.r.l.

  公开号：EP0579129B1

  公开（公告）日：1997-03-05
• METHODS OF DIAGNOSING AND TREATING B CELL ACUTE LYMPHOBLASTIC LEUKEMIA
  申请人：THE GENERAL HOSPITAL CORPORATION

  公开号：US20160251696A1

  公开（公告）日：2016-09-01

  Methods for the diagnosis and treatment of B cell Acute Lymphoblastic Leukemia (B-ALL), based in part on the detection and/or inhibition of Focal Adhesion Kinase (FAK), e.g., phosphorylated FAK (pFAK).
• US5401853A
  申请人：——

  公开号：US5401853A

  公开（公告）日：1995-03-28
• Synthesis of 2-Amino-5-sulfanyl-1,3,4-thiadiazole Derivatives and Evaluation of Their Antidepressant and Anxiolytic Activity
  作者：Francesca Clerici、Donato Pocar、Maddalena Guido、Antonella Loche、Vincenzo Perlini、Mario Brufani

  DOI：10.1021/jm001027w

  日期：2001.3.1

  Recently a series of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives bearing different substituents were synthesized and screened pharmacologically in order to evaluate their central nervous system activity. The purpose of this study was to evaluate the effects of the title compounds on CNS activity by varying the substituents in the thiadiazole moiety. It was found that some of these compounds possess marked antidepressant and anxiolytic properties comparable in efficiency to the reference drugs Imipramine and Diazepam. The most potent compound 3k was further investigated to complete its pharmacological profile with respect to undesired side effects. Behavioral results showed that 3k is a very promising compound, characterized by a mixed antidepressant-anxiolytic activity accompanied by a therapeutic dose range that is essentially 2 orders of magnitude less than that at which side effects such as sedation and amnesia are evident.