(2-Chloro-6-phenyl-imidazo[2,1-b]thiazol-5-yl)-methanol | 851076-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2-Chloro-6-phenyl-imidazo[2,1-b]thiazol-5-yl)-methanol
• 英文别名: (2-Chloro-6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)methanol
• CAS: 851076-76-1
• 化学式: C₁₂H₉ClN₂OS
• 分子量: 264.735
• InChiKey: NJHAJOQSDZPIRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-Chloro-6-phenyl-imidazo[2,1-b]thiazol-5-yl)-methanol 在 三氟化硼乙醚 、 silver(l) oxide 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 13.0h， 生成 2-[(2-Chloro-6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)methyl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Effects of new ubiquinone-imidazo[2,1-b]thiazoles on mitochondrial complex I (NADH-ubiquinone reductase) and on mitochondrial permeability transition pore

  摘要：

  In this work we describe the synthesis of a series of imidazo[2,1-b]thiazoles and 2,3-dihydroimidazo[2,1-b]thiazoles connected by means of a methylene bridge to CoQ(0). These compounds were tested as specific inhibitors of the NADH:ubiquinone reductase activity in mitochondrial membranes. The imidazothiazole system when bound to the quinone ring in place of the isoprenoid lateral side chain, may increase the inhibitory effect (with an IC50 for NADH-Q(1) activity ranging between 0.25 and 0.96 muM) whereas the benzoquinone moiety seems to lose the capability to accept electrons from complex I as indicated by very low maximal velocity elicited by the compounds tested. Moreover the low rotenone sensitivity for almost all of these compounds suggests that they are only partially able to interact with the physiological ubiquinone-reduction site. The compounds were investigated for the capability of increasing the permeability transition of the inner mitochondrial membrane in isolated mitochondria. Unlike CoQ(0), which is considered a mitochondrial membrane permeability transition inhibitor, the new compounds were inducers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.012
• 作为产物：
  描述：

  2-Chloro-6-phenylimidazo[2,1-b][1,3]thiazole-5-carbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以65%的产率得到(2-Chloro-6-phenyl-imidazo[2,1-b]thiazol-5-yl)-methanol
  参考文献：
  名称：

  Effects of new ubiquinone-imidazo[2,1-b]thiazoles on mitochondrial complex I (NADH-ubiquinone reductase) and on mitochondrial permeability transition pore

  摘要：

  In this work we describe the synthesis of a series of imidazo[2,1-b]thiazoles and 2,3-dihydroimidazo[2,1-b]thiazoles connected by means of a methylene bridge to CoQ(0). These compounds were tested as specific inhibitors of the NADH:ubiquinone reductase activity in mitochondrial membranes. The imidazothiazole system when bound to the quinone ring in place of the isoprenoid lateral side chain, may increase the inhibitory effect (with an IC50 for NADH-Q(1) activity ranging between 0.25 and 0.96 muM) whereas the benzoquinone moiety seems to lose the capability to accept electrons from complex I as indicated by very low maximal velocity elicited by the compounds tested. Moreover the low rotenone sensitivity for almost all of these compounds suggests that they are only partially able to interact with the physiological ubiquinone-reduction site. The compounds were investigated for the capability of increasing the permeability transition of the inner mitochondrial membrane in isolated mitochondria. Unlike CoQ(0), which is considered a mitochondrial membrane permeability transition inhibitor, the new compounds were inducers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.08.012