7-氯-N-(邻甲苯基)噻唑并[5,4-D]嘧啶-2-胺 | 1000709-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 1,3-噻唑并[5,4-d]嘧啶
• 中文名称: 7-氯-N-(邻甲苯基)噻唑并[5,4-D]嘧啶-2-胺
• 英文名称: (7-Chloro-thiazolo[5,4-d]pyrimidin-2-yl)-o-tolyl-amine
• 英文别名: 7-chloro-N-o-tolylthiazolo[5,4-d]pyrimidin-2-amine；7-chloro-N-(2-methylphenyl)-[1,3]thiazolo[5,4-d]pyrimidin-2-amine
• CAS: 1000709-51-2
• 化学式: C₁₂H₉ClN₄S
• 分子量: 276.749
• InChiKey: ADKHFPHHMLPJAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 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：
  78.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-氯-N-(邻甲苯基)噻唑并[5,4-D]嘧啶-2-胺 、 对三氟甲基苯胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 Example 17
  参考文献：
  名称：

  Identification and synthesis of 2,7-diamino-thiazolo[5,4-d]pyrimidine derivatives as TRPV1 antagonists

  摘要：

  We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-d]pyrimidines as TRPV1 antagonists. An exploration of the structure-activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-d]pyrimidine led to the identification of several potent TRPV1 antagonists, including 3, 29, 51, and 57. Compound 3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED(50) = 0.5 mg/kg in rats. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.024
• 作为产物：
  描述：

  4,6-二氯-5-氨基嘧啶 、 邻甲苯异硫氰酸酯 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 7-氯-N-(邻甲苯基)噻唑并[5,4-D]嘧啶-2-胺
  参考文献：
  名称：

  Identification and synthesis of 2,7-diamino-thiazolo[5,4-d]pyrimidine derivatives as TRPV1 antagonists

  摘要：

  We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-d]pyrimidines as TRPV1 antagonists. An exploration of the structure-activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-d]pyrimidine led to the identification of several potent TRPV1 antagonists, including 3, 29, 51, and 57. Compound 3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED(50) = 0.5 mg/kg in rats. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.11.024

文献信息

• Thiazolopyrimidine modulators of TRPV1
  申请人：Branstetter Bryan James

  公开号：US20080004253A1

  公开（公告）日：2008-01-03

  Certain TRPV1-modulating thiazolopyrimidine compounds are described. The compounds may be used in pharmaceutical compositions and methods for treating disease states, disorders, and conditions mediated by TRPV1 activity, such as pain, arthritis, itch, cough, asthma, or inflammatory bowel disease.

  描述了某些调节TRPV1的噻唑吡咯啉化合物。这些化合物可以用于制备药物组合物和治疗由TRPV1活性介导的疾病状态、紊乱和病况的方法，如疼痛、关节炎、瘙痒、咳嗽、哮喘或炎症性肠病。
• THIAZOLOPYRIMIDINE MODULATORS OF TRPV1
  申请人：Janssen Pharmaceutica NV

  公开号：EP2044086A2

  公开（公告）日：2009-04-08
• [EN] THIAZOLOPYRIMIDINE MODULATORS OF TRPV1<br/>[FR] MODULATEURS DE TRPV1 À BASE DE THIAZOLOPYRIMIDINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2008005303A2

  公开（公告）日：2008-01-10

  [EN] Certain TRPV1-modulating thiazolopyrimidine compounds are described. The compounds may be used in pharmaceutical compositions and methods for treating disease states, disorders, and conditions mediated by TRPV1 activity, such as pain, arthritis, itch, cough, asthma, or inflammatory bowel disease.
  [FR] La présente invention concerne certains composés de thiazolopyrimidine capables de moduler la protéine TRPV1. Les composés peuvent être utilisés dans des compositions pharmaceutiques et pour des procédés destinés au traitement d'états maladifs, de troubles, et de pathologies médiés par l'activité de la TRPV1, tels que la douleur, l'arthrite, le prurit, la toux, l'asthme, ou la maladie intestinale inflammatoire.
• Identification and synthesis of 2,7-diamino-thiazolo[5,4-d]pyrimidine derivatives as TRPV1 antagonists
  作者：Alec D. Lebsack、Bryan J. Branstetter、Michael D. Hack、Wei Xiao、Matthew L. Peterson、Nadia Nasser、Michael P. Maher、Hong Ao、Anindya Bhattacharya、Mena Kansagara、Brian P. Scott、Lin Luo、Raymond Rynberg、Michele Rizzolio、Sandra R. Chaplan、Alan D. Wickenden、J. Guy Breitenbucher

  DOI：10.1016/j.bmcl.2008.11.024

  日期：2009.1

  We have identified and synthesized a series of 2,7-diamino-thiazolo[5,4-d]pyrimidines as TRPV1 antagonists. An exploration of the structure-activity relationships at the 2-, 5-, and 7-positions of the thiazolo[5,4-d]pyrimidine led to the identification of several potent TRPV1 antagonists, including 3, 29, 51, and 57. Compound 3 was orally bioavailable and afforded a significant reversal of carrageenan-induced thermal hyperalgesia with an ED(50) = 0.5 mg/kg in rats. (C) 2008 Elsevier Ltd. All rights reserved.