2-chloro-6-methylimidazo[2,1-b]thiazole | 851076-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 英文名称: 2-chloro-6-methylimidazo[2,1-b]thiazole
• 英文别名: 2-Chloro-6-methylimidazo[2,1-b][1,3]thiazole
• CAS: 851076-62-5
• 化学式: C₆H₅ClN₂S
• 分子量: 172.638
• InChiKey: KZVORTQHQXOHOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-6-methylimidazo[2,1-b]thiazole 在 sodium tetrahydroborate 、 三氟化硼乙醚 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 为溶剂， 反应 22.0h， 生成
  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：

  一氯丙酮 、 2-amino-5-chloro-thiazole hydrochloride 在 ammonium hydroxide 、 碳酸氢钠 作用下， 以 水 、 四氢呋喃 为溶剂， 反应 20.0h， 生成 2-chloro-6-methylimidazo[2,1-b]thiazole
  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

文献信息

• NOVEL IMIDAZO [4,5-C]QUINOLINE AND IMIDAZO [4,5-C][1,5]NAPHTHYRIDINE DERIVATIVES AS LRRK2 INHIBITORS
  申请人：Pfizer Inc.

  公开号：EP3350178B1

  公开（公告）日：2021-10-20
• [EN] NOVEL IMIDAZO [4,5-C] QUINOLINE AND IMIDAZO [4,5-C][1,5] NAPHTHYRIDINE DERIVATIVES AS LRRK2 INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS IMIDAZO [4,5-C] QUINOLINE ET IMIDAZO [4,5-C] [1,5] NAPHTHYRIDINE UTILISÉS COMME INHIBITEURS DE LRRK2
  申请人：PFIZER

  公开号：WO2017046675A1

  公开（公告）日：2017-03-23

  The present invention provides novel imidazo[4,5-c]quinoline and imidazo[4,5-c][1,5]naphthyridine derivatives of Formula (I), and the pharmaceutically acceptable salts thereof wherein R1, R1a, R1b, R2, R4, R5, R6, X and Z are as defined in the specification. The invention is also directed to pharmaceutical compositions comprising the compounds of Formula (I) and to use of the compounds in the treatment of diseases associated with LRRK2, such as neurodegenerative diseases including Parkinson's disease or Alzheimer's disease, cancer, Crohn's disease or leprosy.
• Effects of new ubiquinone-imidazo[2,1-b]thiazoles on mitochondrial complex I (NADH-ubiquinone reductase) and on mitochondrial permeability transition pore
  作者：Aldo Andreani、Massimiliano Granaiola、Alberto Leoni、Alessandra Locatelli、Rita Morigi、Mirella Rambaldi、Maurizio Recanatini、Giorgio Lenaz、Romana Fato、Christian Bergamini

  DOI：10.1016/j.bmc.2004.08.012

  日期：2004.11

  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.