Example 53 | 1000707-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Example 53
• 英文别名: N2-(2,6-dichloro-phenyl)-5-methanesulfonyl-N7-(4-trifluoromethyl-phenyl)-thiazolo[5,4-d]pyrimidine-2,7-diamine；2-N-(2,6-dichlorophenyl)-5-methylsulfonyl-7-N-[4-(trifluoromethyl)phenyl]-[1,3]thiazolo[5,4-d]pyrimidine-2,7-diamine
• CAS: 1000707-36-7
• 化学式: C₁₉H₁₂Cl₂F₃N₅O₂S₂
• 分子量: 534.37
• InChiKey: DQCPKROIXZPVID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-异丙基哌嗪 、 Example 53 以 2-甲基-2-丁醇 为溶剂， 反应 12.0h， 生成 Example 69
  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：

  Example 52 在 Oxone 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 30.0h， 以69%的产率得到Example 53
  参考文献：
  名称：

  Thiazolopyrimidine modulators of TRPV1

  摘要：

  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。

  公开号：

  US20080004253A1

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。
• 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.