5-ethynyl-4-methyl-2-phenylthiazole | 111600-94-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-ethynyl-4-methyl-2-phenylthiazole
• 英文别名: 5-ethynyl-4-methyl-2-phenyl-1,3-thiazole
• CAS: 111600-94-3
• 化学式: C₁₂H₉NS
• 分子量: 199.276
• InChiKey: FXQCXRHTDGEVNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(迭氮基甲基)-4-甲苯 、 5-ethynyl-4-methyl-2-phenylthiazole 在 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以85%的产率得到4-methyl-5-(1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl)-2-phenylthiazole
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of new 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives

  摘要：

  A new series of 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives, 6a-w have been synthesized by click reaction of substituted benzylazide, 5a-d with 5-ethynyl-4-methyl-2-substituted phenylthiazole, 4a-f. The starting compounds 4-ethynyl-2-substituted phenylthiazole (4a-f) were synthesized from the corresponding thiazole aldehyde by using the Ohira-Bestmann reagent. The structure of the synthesized compounds was determined by spectral analysis. All the synthesized compounds were screened for their preliminary antitubercular activity against Mycobacterium tuberculosis H37Ra (MTB, ATCC 25177). Most of the synthesized compounds reported good activity against M. tuberculosis H37Ra strain with IC50 range of 0.58-8.23 mu g/mL. Compounds 6g and 6k reported good antitubercular activity with MIC90 values of 4.71 and 2.22 mu g/mL, respectively. Potential antimycobacterial activity suggested that these compounds could serve as good lead compounds for further optimization and development of a newer antitubercular candidate.[GRAPHICS].

  DOI：

  10.1007/s00044-019-02310-y
• 作为产物：
  描述：

  4-甲基-2-苯基-1,3-噻唑-5-甲酸乙酯 在 lithium aluminium tetrahydride 、 potassium carbonate 、 2-碘酰基苯甲酸 作用下， 以 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 5-ethynyl-4-methyl-2-phenylthiazole
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of new 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives

  摘要：

  A new series of 5-(1-benzyl-1H-1,2,3-triazol-4-yl)-4-methyl-2-arylthiazole derivatives, 6a-w have been synthesized by click reaction of substituted benzylazide, 5a-d with 5-ethynyl-4-methyl-2-substituted phenylthiazole, 4a-f. The starting compounds 4-ethynyl-2-substituted phenylthiazole (4a-f) were synthesized from the corresponding thiazole aldehyde by using the Ohira-Bestmann reagent. The structure of the synthesized compounds was determined by spectral analysis. All the synthesized compounds were screened for their preliminary antitubercular activity against Mycobacterium tuberculosis H37Ra (MTB, ATCC 25177). Most of the synthesized compounds reported good activity against M. tuberculosis H37Ra strain with IC50 range of 0.58-8.23 mu g/mL. Compounds 6g and 6k reported good antitubercular activity with MIC90 values of 4.71 and 2.22 mu g/mL, respectively. Potential antimycobacterial activity suggested that these compounds could serve as good lead compounds for further optimization and development of a newer antitubercular candidate.[GRAPHICS].

  DOI：

  10.1007/s00044-019-02310-y

文献信息

• Sakamoto, Takao; Nagata, Hideo; Kondo, Yoshinori, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 2, p. 823 - 828
  作者：Sakamoto, Takao、Nagata, Hideo、Kondo, Yoshinori、Shiraiwa, Masafumi、Yamanaka, Hiroshi

  DOI：——

  日期：——