2-hydroxymethyl-1,3-benzothiazole-5-carboxylic acid | 895131-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-hydroxymethyl-1,3-benzothiazole-5-carboxylic acid
• 英文别名: 2-(Hydroxymethyl)benzo[D]thiazole-5-carboxylic acid；2-(hydroxymethyl)-1,3-benzothiazole-5-carboxylic acid
• CAS: 895131-39-2
• 化学式: C₉H₇NO₃S
• 分子量: 209.225
• InChiKey: QTNXZEALACPPBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  98.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-1,3-benzothiazole-5-carboxylic acid 、 对甲基苯乙胺 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(hydroxymethyl)-N-[2-(4-methylphenyl)ethyl]-1,3-benzothiazole-5-carboxamide
  参考文献：
  名称：

  Potent and orally efficacious benzothiazole amides as TRPV1 antagonists

  摘要：

  Benzothiazole amides were identified as TRPV1 antagonists from high throughput screening using recombinant human TRPV1 receptor and structure-activity relationships were explored to pinpoint key pharmacophore interactions. By increasing aqueous solubility, through the attachment of polar groups to the benzothiazole core, and enhancing metabolic stability, by blocking metabolic sites, the drug-like properties and pharmokinetic profiles of benzothiazole compounds were sufficiently optimized such that their therapeutic potential could be verified in rat pharmacological models of pain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.018
• 作为产物：
  描述：

  5-碘-2-甲基苯并[d]噻唑 在 盐酸 、 selenium(IV) oxide 、 sodium tetrahydroborate 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-hydroxymethyl-1,3-benzothiazole-5-carboxylic acid
  参考文献：
  名称：

  Potent and orally efficacious benzothiazole amides as TRPV1 antagonists

  摘要：

  Benzothiazole amides were identified as TRPV1 antagonists from high throughput screening using recombinant human TRPV1 receptor and structure-activity relationships were explored to pinpoint key pharmacophore interactions. By increasing aqueous solubility, through the attachment of polar groups to the benzothiazole core, and enhancing metabolic stability, by blocking metabolic sites, the drug-like properties and pharmokinetic profiles of benzothiazole compounds were sufficiently optimized such that their therapeutic potential could be verified in rat pharmacological models of pain. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.018

文献信息

• Benzothiazolecarboxamides
  申请人：Brown William

  公开号：US20080108676A1

  公开（公告）日：2008-05-08

  The present invention relates to new compounds of formula I, (I) wherein R 1 to R 4 , m, n and p, are as defined as in formula I, or salts, solvates or solvated salts thereof, processes for their preparation and to a new intermediate used in the preparation thereof, pharmaceutical formulations containing said compounds and to the use of said compounds in therapy.

  本发明涉及一种新的化合物I，其化学式为（I），其中R1至R4，m，n和p如化学式I中所定义，或其盐，溶剂合物或溶剂化盐，其制备方法以及用于其制备的新中间体，含有该化合物的药物制剂以及该化合物在治疗中的应用。
• WO2006/68592
  申请人：——

  公开号：——

  公开（公告）日：——
• Potent and orally efficacious benzothiazole amides as TRPV1 antagonists
  作者：Yevgeni Besidski、William Brown、Johan Bylund、Michael Dabrowski、Sophie Dautrey、Magali Harter、Lucy Horoszok、Yin Hu、Dean Johnson、Shawn Johnstone、Paul Jones、Sandrine Leclerc、Karin Kolmodin、Inger Kers、Maryse Labarre、Denis Labrecque、Jennifer Laird、Therese Lundström、John Martino、Mickaël Maudet、Alexander Munro、Martin Nylöf、Andrea Penwell、Didier Rotticci、Andis Slaitas、Anna Sundgren-Andersson、Mats Svensson、Gitte Terp、Huascar Villanueva、Christopher Walpole、Ronald Zemribo、Andrew M. Griffin

  DOI：10.1016/j.bmcl.2012.08.018

  日期：2012.10

  Benzothiazole amides were identified as TRPV1 antagonists from high throughput screening using recombinant human TRPV1 receptor and structure-activity relationships were explored to pinpoint key pharmacophore interactions. By increasing aqueous solubility, through the attachment of polar groups to the benzothiazole core, and enhancing metabolic stability, by blocking metabolic sites, the drug-like properties and pharmokinetic profiles of benzothiazole compounds were sufficiently optimized such that their therapeutic potential could be verified in rat pharmacological models of pain. (C) 2012 Elsevier Ltd. All rights reserved.