2-[(benzothiazol-2-yl)thio] acetyl chloride | 80357-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-[(benzothiazol-2-yl)thio] acetyl chloride
• 英文别名: [(1,3-Benzothiazol-2-yl)sulfanyl]acetyl chloride；2-(1,3-benzothiazol-2-ylsulfanyl)acetyl chloride
• CAS: 80357-75-1
• 化学式: C₉H₆ClNOS₂
• 分子量: 243.738
• InChiKey: LVXODBPVMFDPHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(benzothiazol-2-yl)thio] acetyl chloride 在 sodium azide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 2-(1,3-benzothiazol-2-ylsulfanyl)acetyl azide
  参考文献：
  名称：

  Benzothiazole hydroxy ureas as inhibitors of 5-lipoxygenase: use of the hydroxyurea moiety as a replacement for hydroxamic acid

  摘要：

  A novel series of N-[(2-benzothiazolylthio)alkyl]-N'-hydroxyurea derivatives (9-25) was synthesized and evaluated for biological activity as inhibitors of 5-lipoxygenase both in vivo (mouse zymosan peritonitis assay) and in vitro (Ca2+ ionophore-stimulated human peripheral blood leukocyte model). The compounds of this series were based on the corresponding hydroxamic acid derivatives (1, 3, 4, and 5) which were moderately active in vitro but inactive in vivo. A number of compounds in the hydroxyurea series exhibited oral activity for 5-lipoxygenase inhibition. Results of studies relating structure to in vivo and in vitro 5-lipoxygenase activity are reported.

  DOI：

  10.1021/jm00095a012
• 作为产物：
  描述：

  (1,3-苯并噻唑-2-硫基)乙酸 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 2-[(benzothiazol-2-yl)thio] acetyl chloride
  参考文献：
  名称：

  Benzothiazole hydroxy ureas as inhibitors of 5-lipoxygenase: use of the hydroxyurea moiety as a replacement for hydroxamic acid

  摘要：

  A novel series of N-[(2-benzothiazolylthio)alkyl]-N'-hydroxyurea derivatives (9-25) was synthesized and evaluated for biological activity as inhibitors of 5-lipoxygenase both in vivo (mouse zymosan peritonitis assay) and in vitro (Ca2+ ionophore-stimulated human peripheral blood leukocyte model). The compounds of this series were based on the corresponding hydroxamic acid derivatives (1, 3, 4, and 5) which were moderately active in vitro but inactive in vivo. A number of compounds in the hydroxyurea series exhibited oral activity for 5-lipoxygenase inhibition. Results of studies relating structure to in vivo and in vitro 5-lipoxygenase activity are reported.

  DOI：

  10.1021/jm00095a012

文献信息

• Synthesis and reactions of 2-mercaptobenzothiazole derivatives of expected biological activity
  作者：Abou El-Fotooh G. Hammam、Nabil M. Youssif

  DOI：10.1021/je00028a032

  日期：1982.4
• ——
  作者：V. I. Kelarev、M. A. Silin、K. I. Kobrakov、I. I. Rybina、V. K. Korolev

  DOI：10.1023/a:1025638910987

  日期：——
• Benzothiazole hydroxy ureas as inhibitors of 5-lipoxygenase: use of the hydroxyurea moiety as a replacement for hydroxamic acid
  作者：Michael N. Greco、William E. Hageman、Eugene T. Powell、Joseph J. Tighe、Francis J. Persico

  DOI：10.1021/jm00095a012

  日期：1992.8

  A novel series of N-[(2-benzothiazolylthio)alkyl]-N'-hydroxyurea derivatives (9-25) was synthesized and evaluated for biological activity as inhibitors of 5-lipoxygenase both in vivo (mouse zymosan peritonitis assay) and in vitro (Ca2+ ionophore-stimulated human peripheral blood leukocyte model). The compounds of this series were based on the corresponding hydroxamic acid derivatives (1, 3, 4, and 5) which were moderately active in vitro but inactive in vivo. A number of compounds in the hydroxyurea series exhibited oral activity for 5-lipoxygenase inhibition. Results of studies relating structure to in vivo and in vitro 5-lipoxygenase activity are reported.