4-(dibromomethyl)-5-chlorocarbonyl-2-(4-chlorophenyl)thiazole | 1272385-09-7

• 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-(dibromomethyl)-5-chlorocarbonyl-2-(4-chlorophenyl)thiazole
• 英文别名: 2-(4-Chlorophenyl)-4-(dibromomethyl)-1,3-thiazole-5-carbonyl chloride
• CAS: 1272385-09-7
• 化学式: C₁₁H₅Br₂Cl₂NOS
• 分子量: 429.947
• InChiKey: DGHZAMJPFAYZOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(dibromomethyl)-5-chlorocarbonyl-2-(4-chlorophenyl)thiazole 在 ammonium hydroxide 作用下， 以84%的产率得到4-(dibromomethyl)-2-(4-chlorophenyl)thiazole-5-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Thiazoles Targeting Flavivirus Envelope Proteins

  摘要：

  A series of third-generation analogues of methyl 4-(dibromomethyl)-2-(4-chlorophenyl)thiazole-5-carboxylate (1), which had the most potent antiviral activity among the first- and second-generation compounds, have been synthesized and tested against yellow fever virus using a cell-based assay. The compounds were designed with the objectives of improving metabolic stability, therapeutic index, and antiviral potency. The biological effects of C4 and C5 substitution were examined. The methylthio ester and the dihydroxpropylamide analogues had the best antiviral potencies and improved therapeutic indices and metabolic stabilities relative to the parent compound 1.

  DOI：

  10.1021/jm1013538
• 作为产物：
  描述：

  2-(4-氯苯基)-4-甲基-1,3-噻唑-5-羧酸 在 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 生成 4-(dibromomethyl)-5-chlorocarbonyl-2-(4-chlorophenyl)thiazole
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Thiazoles Targeting Flavivirus Envelope Proteins

  摘要：

  A series of third-generation analogues of methyl 4-(dibromomethyl)-2-(4-chlorophenyl)thiazole-5-carboxylate (1), which had the most potent antiviral activity among the first- and second-generation compounds, have been synthesized and tested against yellow fever virus using a cell-based assay. The compounds were designed with the objectives of improving metabolic stability, therapeutic index, and antiviral potency. The biological effects of C4 and C5 substitution were examined. The methylthio ester and the dihydroxpropylamide analogues had the best antiviral potencies and improved therapeutic indices and metabolic stabilities relative to the parent compound 1.

  DOI：

  10.1021/jm1013538

文献信息

• [EN] SUBSTITUTED THIAZOLES FOR USE AS ANTIVIRAL AGENTS<br/>[FR] THIAZOLES SUBSTITUÉS UTILISÉS EN TANT QU'AGENTS ANTIVIRAUX
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2012109573A1

  公开（公告）日：2012-08-16

  Described herein are substituted thiazoles. Also described herein are preparations of substituted thiazoles, and the use of substituted thiazoles as antiviral agents.