4-Ethyl-[1,2,3]thiadiazole-5-carbonyl chloride | 889939-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-Ethyl-[1,2,3]thiadiazole-5-carbonyl chloride
• 英文别名: 4-ethylthiadiazole-5-carbonyl chloride
• CAS: 889939-72-4
• 化学式: C₅H₅ClN₂OS
• 分子量: 176.626
• InChiKey: LDFUVWIMAFQDBW-UHFFFAOYSA-N

物化性质

• 沸点：
  271.7±42.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N-(2-aminoethyl)quinoline-8-carboxamide 、 4-Ethyl-[1,2,3]thiadiazole-5-carbonyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-ethyl-N-(2-(quinoline-8-carboxamido)ethyl)-1,2,3-thiadiazole-5-carboxamide
  参考文献：
  名称：

  Naphthalimide and quinoline derivatives as inhibitors for insect N-acetyl-β-d-hexosaminidase

  摘要：

  Insect chitinolytic beta-N-acetyl-D-hexosaminidase, such as OfHex1 from Ostrinia furnacalis, is a potential target for insecticide design. Among the known OfHex1 inhibitors, Q2 is of great interest because it is the first non-carbohydrate inhibitor. In this study, we designed and synthesized a series of Q2 derivatives by replacing the thiadiazole and naphthalimide groups and changing the linker length. Compound 3m showed the best inhibitory activity with a K-i value of 034 mu mol/L against OfHex1, which is about one-quarter that of Q2 (K-i = 1.4 mu mol/L). Compound 6a showed the best inhibitory activity among the quinoline-containing derivatives (K-i = 2.3 mu mol/L). Molecular docking indicated that although 3m, 6a, and Q2 binding the active pocket of OfHex1 in similar mode, compound 3m engaged better than the other compounds in intermolecular interaction with OfHex1. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.01.023
• 作为产物：
  描述：

  4-乙基-1,2-3-噻二唑-5-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-Ethyl-[1,2,3]thiadiazole-5-carbonyl chloride
  参考文献：
  名称：

  Naphthalimide and quinoline derivatives as inhibitors for insect N-acetyl-β-d-hexosaminidase

  摘要：

  Insect chitinolytic beta-N-acetyl-D-hexosaminidase, such as OfHex1 from Ostrinia furnacalis, is a potential target for insecticide design. Among the known OfHex1 inhibitors, Q2 is of great interest because it is the first non-carbohydrate inhibitor. In this study, we designed and synthesized a series of Q2 derivatives by replacing the thiadiazole and naphthalimide groups and changing the linker length. Compound 3m showed the best inhibitory activity with a K-i value of 034 mu mol/L against OfHex1, which is about one-quarter that of Q2 (K-i = 1.4 mu mol/L). Compound 6a showed the best inhibitory activity among the quinoline-containing derivatives (K-i = 2.3 mu mol/L). Molecular docking indicated that although 3m, 6a, and Q2 binding the active pocket of OfHex1 in similar mode, compound 3m engaged better than the other compounds in intermolecular interaction with OfHex1. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.01.023