methyl 2-(4-chlorophenyl)-4-(methoxymethyl)thiazole-5-carboxylate | 1222188-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(4-chlorophenyl)-4-(methoxymethyl)thiazole-5-carboxylate
• 英文别名: Methyl 2-(4-chlorophenyl)-4-(methoxymethyl)-1,3-thiazole-5-carboxylate
• CAS: 1222188-64-8
• 化学式: C₁₃H₁₂ClNO₃S
• 分子量: 297.762
• InChiKey: SCBSPUYXFDQQOW-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101 °C
• 沸点：
  427.1±55.0 °C(predicted)
• 密度：
  1.314±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-chlorophenyl)-4-(methoxymethyl)thiazole-5-carboxylate 在 氯化亚砜 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 11.0h， 生成 2-(4-chlorophenyl)-4-(methoxymethyl)thiazole-5-carbonyl chloride
  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 、 2-氯-4-甲氧基-3-氧代-丁酸甲酯 以 乙醇 为溶剂， 反应 24.0h， 以74.4%的产率得到methyl 2-(4-chlorophenyl)-4-(methoxymethyl)thiazole-5-carboxylate
  参考文献：
  名称：

  用 NBS 氧化苄基甲基醚，选择性地提供芳香醛或芳香甲酯

  摘要：

  苄基甲基醚的单溴化或二溴化可以通过控制 NBS 的量和温度来实现。从单溴化中间体中去除甲基溴产生芳香醛，而二溴化中间体的水解以良好的产率提供芳香甲基酯。

  DOI：

  10.1021/jo1004313

文献信息

• An Oxidation of Benzyl Methyl Ethers with NBS that Selectively Affords Either Aromatic Aldehydes or Aromatic Methyl Esters
  作者：Abdelrahman S. Mayhoub、Arindam Talukdar、Mark Cushman

  DOI：10.1021/jo1004313

  日期：2010.5.21

  Either mono- or dibromination of benzyl methyl ethers can be achieved by controlling the amount of NBS and the temperature. Elimination of methyl bromide from the monobrominated intermediates produces aromatic aldehydes, whereas hydrolysis of the dibrominated intermediates affords aromatic methyl esters in good yields.

  苄基甲基醚的单溴化或二溴化可以通过控制 NBS 的量和温度来实现。从单溴化中间体中去除甲基溴产生芳香醛，而二溴化中间体的水解以良好的产率提供芳香甲基酯。
• 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.