2,6-dichlorothiazolo[4,5-b]pyridine | 960535-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,6-dichlorothiazolo[4,5-b]pyridine
• 英文别名: 2-Chloro-6-chloro[1,3]thiazolo[4,5-b]pyridine；2,6-Dichloro-[1,3]thiazolo[4,5-b]pyridine
• CAS: 960535-43-7
• 化学式: C₆H₂Cl₂N₂S
• 分子量: 205.067
• InChiKey: NSOMSBHAMKHHNR-UHFFFAOYSA-N

物化性质

• 沸点：
  283.0±20.0 °C(Predicted)
• 密度：
  1.662±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-dichlorothiazolo[4,5-b]pyridine 、 tert-butyl 3-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate 在 palladium diacetate 、 三苯基膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以21%的产率得到
  参考文献：
  名称：

  Discovery of Novel 2-((Pyridin-3-yloxy)methyl)piperazines as α7 Nicotinic Acetylcholine Receptor Modulators for the Treatment of Inflammatory Disorders

  摘要：

  Herein we report the design, synthesis, and structure activity relationships for a new class of alpha 7 nicotinic acetylcholine receptor (nAChR) modulators based on the 2-((pyridin-3-yloxy)methyl)piperazine scaffold. The oxazolo[4,5-b]pyridine, (R)-18, and 4-methoxyphenylurea, (R)-47, were identified as potent and selective modulators of the alpha 7 nAChR with favorable in vitro safety profiles and good oral bioavailability in mouse. Both compounds were shown to significantly inhibit cellular infiltration in a murine model of allergic lung inflammation. Despite the structural and in vivo functional similarities in the compounds, only (R)-18 was shown to be an agonist. Compound (R)-47 demonstrated silent agonist activity. These data support the hypothesis that the anti-inflammatory activity of the alpha 7 nAChR is mediated by a signal transduction pathway that is independent of ion current.

  DOI：

  10.1021/jm5004599

文献信息

• [EN] COMPOUNDS WITH TWO FUSED BICYCLIC HETEROARYL MOIETIES AS MODULATORS OF LEUKOTRIENE A4 HYDROLASE<br/>[FR] COMPOSÉS POSSÉDANT DEUX GROUPEMENTS HÉTÉROARYLE BICYCLIQUES CONDENSÉS EN TANT QUE MODULATEURS DE LA LEUCOTRIÈNE A4 HYDROLASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2010132599A1

  公开（公告）日：2010-11-18

  Compounds with two fused bicyclic heteroaryl moieties of formula I and their pharmaceutical compositions, and methods of using them as leukotriene A4 hydrolase (LTA4H) modulators and for the treatment of diseases, disorders and conditions mediated by LTA4H.

  具有式I中两个融合的双环杂环芳基部分的化合物及其药物组合物，以及将它们用作白三烯A4水解酶（LTA4H）调节剂，并用于治疗由LTA4H介导的疾病、紊乱和病况的方法。
• Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene A4 hydrolase
  申请人：Bacani Genesis M.

  公开号：US20090258854A1

  公开（公告）日：2009-10-15

  Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amine compounds are described, which are useful as LTA4 hydrolase (LTA4H) modulators. Such compounds may be used in pharmaceutical compositions and methods for modulation of LTA4H and for the treatment of disease states, disorders, and conditions mediated by LTA4 hydrolase activity.

  描述了噻唑吡啶-2-氧基苯基和噻唑吡嗪-2-氧基苯基胺化合物，这些化合物可作为LTA4水解酶（LTA4H）调节剂。这些化合物可以用于制备药物组合物，用于调节LTA4H并治疗由LTA4水解酶活性介导的疾病状态、疾病和症状。
• Thyazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene A4 hydrolase
  申请人：Bacani Genesis M.

  公开号：US20110159563A1

  公开（公告）日：2011-06-30

  Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amine compounds are described, which are useful as LTA4 hydrolase (LTA4H) modulators. Such compounds may be used in pharmaceutical compositions and methods for modulation of LTA4H and for the treatment of disease states, disorders, and conditions mediated by LTA4 hydrolase activity.

  本文介绍了一种Thiazolopyridin-2-yloxy-phenyl和thiazolopyrazin-2-yloxy-phenyl胺类化合物，这些化合物可用作LTA4水解酶（LTA4H）调节剂。这些化合物可以用于制备药物组合物和方法，用于调节LTA4H并治疗由LTA4水解酶活性介导的疾病状态、疾患和病情。
• COMPOUNDS WITH TWO FUSED BICYCLIC HETEROARYL MOIETIES AS MODULATORS OF LEUKOTRIENE A4 HYDROLASE
  申请人：Bacani Genesis

  公开号：US20100292208A1

  公开（公告）日：2010-11-18

  Compounds with two fused bicyclic heteroaryl moieties and their pharmaceutical compositions, and methods of using them as leukotriene A 4 hydrolase (LTA 4 H) modulators and for the treatment of diseases, disorders and conditions mediated by LTA 4 H.

  具有两个融合的杂环芳基基团的化合物及其制药组合物，以及将它们用作白三烯A4水解酶（LTA4H）调节剂的方法，以及用于治疗由LTA4H介导的疾病，障碍和情况的方法。
• Azabenzthiazole inhibitors of leukotriene A4 hydrolase
  作者：Virginia M. Tanis、Genesis M. Bacani、Jonathan M. Blevitt、Christa C. Chrovian、Shelby Crawford、Aimee De Leon、Anne M. Fourie、Laurent Gomez、Cheryl A. Grice、Krystal Herman、Aaron M. Kearney、Adrienne M. Landry-Bayle、Alice Lee-Dutra、Jay Nelson、Jason P. Riley、Alejandro Santillán、John J.M. Wiener、Xiaohua Xue、Arlene L. Young

  DOI：10.1016/j.bmcl.2012.10.036

  日期：2012.12

  Previously, benzthiazole containing LTA4H inhibitors were discovered that were potent (1-3), but were associated with the potential for a hERG liability. Utilizing medicinal chemistry first principles (e. g., introducing rigidity, lowering cLogD) a new benzthiazole series was designed, congeners of 1-3, which led to compounds 7a, 7c, 12a-d which exhibited LTA4H IC50 = 3-6 nM and hERG Dofetilide Binding IC50 = 8.9-> >10 mu M. (C) 2012 Elsevier Ltd. All rights reserved.