6-phenyl-2-m-tolylimidazo[2,1-b][1,3,4]thiadiazole | 73653-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-phenyl-2-m-tolylimidazo[2,1-b][1,3,4]thiadiazole
• 英文别名: 6-phenyl-2-m-tolyl-imidazo[2,1-b][1,3,4]thiadiazole
• CAS: 73653-69-7
• 化学式: C₁₇H₁₃N₃S
• 分子量: 291.376
• InChiKey: OKPRTQJUCYIMEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  30.19
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  间甲基苯甲酸 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 6-phenyl-2-m-tolylimidazo[2,1-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Design, synthesis and evaluation of small molecule imidazo[2,1-b][1,3,4]thiadiazoles as inhibitors of transforming growth factor-β type-I receptor kinase (ALK5)

  摘要：

  A new series of imidazo[2,1-b][1,3,4]thiadiazoles 5(a-g), 6(a-g), 9(a-i) and 12(a-h) were synthesized as transforming growth factor-beta (TGF-beta) type I receptor (also known as activin receptor-like kinase 5 or ALK5) inhibitors. These compounds were evaluated for their ALK5 inhibitory activity in an enzyme assay and their TGF-beta -induced Smad2/3 phosphorylation inhibitory activity in a cell-based assay. Compound 6d, 2-(5((2-cyclopropy1-6-(4-fluorophenyl) imidazo [2,1-b][1,3,4]thiadiazol-5-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl) acetic acid, shows prominent ALK5 inhibition (IC50 = 0.0012 mu M) and elective inhibition (91%) against the P38 alpha kinase at10 mu M. The binding mode of compound 6d by XP docking studies shows that it fits well into the active site cavity of ALK5 by forming broad and tight interactions. Lipinski's rule and in silica ADME pharmacokinetic parameters are within the acceptable range defined for human use thereby indicating their potential as a drug-like molecules. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.002

文献信息

• Mohan, Jag; Singh, Virender; Kataria, Sangeeta, Journal of the Chinese Chemical Society, 1994, vol. 41, # 5, p. 617 - 619
  作者：Mohan, Jag、Singh, Virender、Kataria, Sangeeta

  DOI：——

  日期：——