tert-butyl [2-(hydroxymethyl)-1,3-benzothiazol-5-yl]carbamate | 790689-70-2

• 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: tert-butyl [2-(hydroxymethyl)-1,3-benzothiazol-5-yl]carbamate
• 英文别名: Tert-butyl [2-(hydroxymethyl)-1,3-benzothiazol-5-yl]carbamate；tert-butyl N-[2-(hydroxymethyl)-1,3-benzothiazol-5-yl]carbamate
• CAS: 790689-70-2
• 化学式: C₁₃H₁₆N₂O₃S
• 分子量: 280.348
• InChiKey: ARMFVXKXISKGIW-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±22.0 °C(Predicted)
• 密度：
  1.340±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl [2-(hydroxymethyl)-1,3-benzothiazol-5-yl]carbamate 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 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-(diethylaminomethyl)-N-[2-(hydroxymethyl)-1,3-benzothiazol-5-yl]benzamide
  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：

  tert-butyl (2-methylbenzo[d]thiazol-5-yl)carbamate 在 selenium(IV) oxide 、 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 tert-butyl [2-(hydroxymethyl)-1,3-benzothiazol-5-yl]carbamate
  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

• [EN] NEW HETEROCYCLIC AMIDES EXHIBITING AN INHIBITORY ACTIVITY AT THE VANILLOID RECEPTOR 1 (VR1).<br/>[FR] NOUVEAUX AMIDES HETEROCYCLIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004096784A1

  公开（公告）日：2004-11-11

  The present invention relates to new compounds of formula I, wherein R1 to R8 are as defined as in formula I, or salts, solvates or solvated salts thereof, processes for their preparation and to new intermediates used in the preparation thereof, pharmaceutical compositions containing said compounds and to the use of said compounds in therapy.

  本发明涉及公式I的新化合物，其中R1至R8如公式I中所定义，或其盐、溶剂合物或溶剂化合盐，以及用于其制备的新中间体，含有所述化合物的药物组合物以及所述化合物在治疗中的用途。