4-(4-chlorophenyl)-2-(1-methylpiperidin-4-yl)thiazole | 88654-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-chlorophenyl)-2-(1-methylpiperidin-4-yl)thiazole
• 英文别名: Piperidine, 4-[4-(4-chlorophenyl)-2-thiazolyl]-1-methyl-；4-(4-chlorophenyl)-2-(1-methylpiperidin-4-yl)-1,3-thiazole
• CAS: 88654-20-0
• 化学式: C₁₅H₁₇ClN₂S
• 分子量: 292.832
• InChiKey: ONHCIOYNFHOFME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  哌啶-4-甲酰胺 在 劳森试剂 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 4-(4-chlorophenyl)-2-(1-methylpiperidin-4-yl)thiazole
  参考文献：
  名称：

  Diarylthiazole: An Antimycobacterial Scaffold Potentially Targeting PrrB-PrrA Two-Component System

  摘要：

  Diarylthiazole (DAT), a hit from diversity screening, was found to have potent antimycobacterial activity against Mycobacterium tuberculosis (Mtb). In a systematic medicinal chemistry exploration, we demonstrated chemical opportunities to optimize the potency and physicochemical properties. The effort led to more than 10 compounds with submicromolar MICs and desirable physicochemical properties. The potent antimycobacterial activity, in conjunction with low molecular weight, made the series an attractive lead (antibacterial ligand efficiency (ALE)>0.4). The series exhibited excellent bactericidal activity and was active against drug-sensitive and resistant Mtb. Mutational analysis showed that mutations in prrB impart resistance to DAT compounds but not to reference drugs tested. The sensor kinase PrrB belongs to the PrrBA two component system and is potentially the target for DAT. PrrBA is a conserved, essential regulatory mechanism in Mtb and has been shown to have a role in virulence and metabolic adaptation to stress. Hence, DATs provide an opportunity to understand a completely new target system for antimycobacterial drug discovery.

  DOI：

  10.1021/jm500833f

文献信息

• KUROYAN, R. A.;MARKOSYAN, A. I.;VARTANYAN, S. A., ARM. XIM. ZH., 1983, 36, N 9, 610-614
  作者：KUROYAN, R. A.、MARKOSYAN, A. I.、VARTANYAN, S. A.

  DOI：——

  日期：——