1-(4-(dibromomethyl)-2-(4-chlorophenyl)thiazol-5-yl)ethanone | 1272385-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-(dibromomethyl)-2-(4-chlorophenyl)thiazol-5-yl)ethanone
• 英文别名: 1-[2-(4-Chlorophenyl)-4-(dibromomethyl)-1,3-thiazol-5-yl]ethanone
• CAS: 1272385-38-2
• 化学式: C₁₂H₈Br₂ClNOS
• 分子量: 409.529
• InChiKey: JGISAVGHVQNRPK-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C
• 沸点：
  481.9±55.0 °C(predicted)
• 密度：
  1.825±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1-(4-(dibromomethyl)-2-(4-chlorophenyl)thiazol-5-yl)ethanone 、 N,N-二甲基甲酰胺二甲基缩醛 以 甲苯 为溶剂， 反应 24.0h， 以66%的产率得到(E)-1-(4-(dibromomethyl)-2-(4-chlorophenyl)thiazol-5-yl)-3-(dimethylamino)prop-2-en-1-one
  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：

  4-氯硫代苯甲酰胺 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 36.0h， 生成 1-(4-(dibromomethyl)-2-(4-chlorophenyl)thiazol-5-yl)ethanone
  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.
• Design, Synthesis, and Biological Evaluation of Thiazoles Targeting Flavivirus Envelope Proteins
  作者：Abdelrahman S. Mayhoub、Mansoora Khaliq、Richard J. Kuhn、Mark Cushman

  DOI：10.1021/jm1013538

  日期：2011.3.24

  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.