2-Amino-5-napthyl-(1)-methylmercapto-1.3.4-thiadiazol | 100728-67-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Amino-5-napthyl-(1)-methylmercapto-1.3.4-thiadiazol
• 英文别名: 5-[(1-Naphthylmethyl)thio]-1,3,4-thiadiazol-2-amine；5-(naphthalen-1-ylmethylsulfanyl)-1,3,4-thiadiazol-2-amine
• CAS: 100728-67-4
• 化学式: C₁₃H₁₁N₃S₂
• mdl: MFCD00442953
• 分子量: 273.382
• InChiKey: FVZXNLYVWPHMAT-UHFFFAOYSA-N

物化性质

• 沸点：
  509.0±43.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-(1-benzyl-1H-indol-3-yl)-2-cyanoacrylate 、 2-Amino-5-napthyl-(1)-methylmercapto-1.3.4-thiadiazol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以63%的产率得到(E)-3-(1-benzyl-1H-indol-3-yl)-2-cyano-N-(5-((naphthalen-1-ylmethyl)sulfanyl)-1,3,4-thiadiazol-2-yl)prop-2-enamide
  参考文献：
  名称：

  Identification of novel thiadiazoloacrylamide analogues as inhibitors of dengue-2 virus NS2B/NS3 protease

  摘要：

  Dengue virus is endemic throughout tropical and subtropical regions, and cause severe epidemic diseases. The NS2B/NS3 protease is a promising drug target for dengue virus. Herein, we report the discovery and modification of a novel class of thiadiazoloacrylamide derivatives with potent inhibitory activity against the NS2B/NS3 protease. Thiadiazolopyrimidinone 1 was firstly determined as a new chemical structure against NS2B/NS3 from a commercial compound library. Then, we sought to identify similar compounds with the thiadiazoloacrylamide core that would exhibit better activity. A series of analogues were synthesized and fourteen of them were identified with strong inhibitory activities, in which the nitrile group in the linker part was discovered as an essential group for the inhibitory activity. The best of these (8b) demonstrated an IC50 at 2.24 mu M based on in vitro DENV2 NS2B-NS3pro assays. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.09.057
• 作为产物：
  描述：

  1-mercaptomethylnaphthalene 、 2-氨基-5-巯基-1,3,4-噻二唑 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 2-Amino-5-napthyl-(1)-methylmercapto-1.3.4-thiadiazol
  参考文献：
  名称：

  Identification of novel thiadiazoloacrylamide analogues as inhibitors of dengue-2 virus NS2B/NS3 protease

  摘要：

  Dengue virus is endemic throughout tropical and subtropical regions, and cause severe epidemic diseases. The NS2B/NS3 protease is a promising drug target for dengue virus. Herein, we report the discovery and modification of a novel class of thiadiazoloacrylamide derivatives with potent inhibitory activity against the NS2B/NS3 protease. Thiadiazolopyrimidinone 1 was firstly determined as a new chemical structure against NS2B/NS3 from a commercial compound library. Then, we sought to identify similar compounds with the thiadiazoloacrylamide core that would exhibit better activity. A series of analogues were synthesized and fourteen of them were identified with strong inhibitory activities, in which the nitrile group in the linker part was discovered as an essential group for the inhibitory activity. The best of these (8b) demonstrated an IC50 at 2.24 mu M based on in vitro DENV2 NS2B-NS3pro assays. (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2014.09.057

文献信息

• Use of acyl urea compounds for controlling endoparasites and
  申请人：Ciba-Geigy

  公开号：US05420163A1

  公开（公告）日：1995-05-30

  A method of systemically controlling endoparasites and ectoparasites of warm-blooded animals by orally or percutaneously administering to the animal a parasiticidally effective amount of an acyl urea compound.

  一种通过口服或经皮给予温血动物寄生虫杀虫剂有效量的酰基脲化合物来系统性地控制内寄生虫和外寄生虫的方法。
• Identification of novel thiadiazoloacrylamide analogues as inhibitors of dengue-2 virus NS2B/NS3 protease
  作者：Hailong Liu、Ruoming Wu、Yanyan Sun、Yan Ye、Jing Chen、Xiaomin Luo、Xu Shen、Hong Liu

  DOI：10.1016/j.bmc.2014.09.057

  日期：2014.11

  Dengue virus is endemic throughout tropical and subtropical regions, and cause severe epidemic diseases. The NS2B/NS3 protease is a promising drug target for dengue virus. Herein, we report the discovery and modification of a novel class of thiadiazoloacrylamide derivatives with potent inhibitory activity against the NS2B/NS3 protease. Thiadiazolopyrimidinone 1 was firstly determined as a new chemical structure against NS2B/NS3 from a commercial compound library. Then, we sought to identify similar compounds with the thiadiazoloacrylamide core that would exhibit better activity. A series of analogues were synthesized and fourteen of them were identified with strong inhibitory activities, in which the nitrile group in the linker part was discovered as an essential group for the inhibitory activity. The best of these (8b) demonstrated an IC50 at 2.24 mu M based on in vitro DENV2 NS2B-NS3pro assays. (C) 2014 Published by Elsevier Ltd.