3-(2-Bromo-4-isopropyl-phenyl)-7-(cyclopropylmethyl-propyl-amino)-5-methyl-3H-thiazolo[4,5-d]pyrimidine-2-thione | 228254-28-2

• 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: 3-(2-Bromo-4-isopropyl-phenyl)-7-(cyclopropylmethyl-propyl-amino)-5-methyl-3H-thiazolo[4,5-d]pyrimidine-2-thione
• 英文别名: 3-(2-bromo-4-propan-2-ylphenyl)-7-[cyclopropylmethyl(propyl)amino]-5-methyl-[1,3]thiazolo[4,5-d]pyrimidine-2-thione
• CAS: 228254-28-2
• 化学式: C₂₂H₂₇BrN₄S₂
• 分子量: 491.519
• InChiKey: GVAHQUYUMYBUDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2-Bromo-4-isopropyl-phenyl)-7-(cyclopropylmethyl-propyl-amino)-5-methyl-3H-thiazolo[4,5-d]pyrimidine-2-thione 在 水 、 硫酸二甲酯 作用下， 生成 3-(2-Bromo-4-isopropyl-phenyl)-7-(cyclopropylmethyl-propyl-amino)-5-methyl-3H-thiazolo[4,5-d]pyrimidin-2-one
  参考文献：
  名称：

  Thiazolo[4,5-d]pyrimidine thiones and -ones as corticotropin-releasing hormone (CRH-R1) receptor antagonists

  摘要：

  A series of thiazolo[4,5-d]pyrimidine thiones and -ones was prepared and discovered to have good binding affinity to the CRH-R1 receptor, thus showing promise as a new class of potential anxiolytics and/or antidepressants. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00159-6
• 作为产物：
  描述：

  2-溴-4-异丙基苯胺 在 sodium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.83h， 生成 3-(2-Bromo-4-isopropyl-phenyl)-7-(cyclopropylmethyl-propyl-amino)-5-methyl-3H-thiazolo[4,5-d]pyrimidine-2-thione
  参考文献：
  名称：

  Thiazolo[4,5-d]pyrimidine thiones and -ones as corticotropin-releasing hormone (CRH-R1) receptor antagonists

  摘要：

  A series of thiazolo[4,5-d]pyrimidine thiones and -ones was prepared and discovered to have good binding affinity to the CRH-R1 receptor, thus showing promise as a new class of potential anxiolytics and/or antidepressants. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00159-6

文献信息

• 10.3390/molecules29153647
  作者：Islam, Md Rabiul、Markatos, Christos、Pirmettis, Ioannis、Papadopoulos, Minas、Karageorgos, Vlasios、Liapakis, George、Fahmy, Hesham

  DOI：10.3390/molecules29153647

  日期：——

  with CRF receptor binding may be of value to treat neuropsychiatric stress-related disorders. Also, CRF1R antagonists have recently emerged as potential treatment options for congenital adrenal hyperplasia. Previously, several series of CRF1 receptor antagonists were developed by our group. In continuation of our efforts in this direction, herein we report the synthesis and biological evaluation of a new

  促肾上腺皮质激素释放因子（CRF）是下丘脑分泌的一种关键神经肽激素。它是 HPA 轴的主要激素，协调对压力的生理和行为反应。许多疾病，包括焦虑、抑郁、成瘾复发等，都与该系统的过度激活有关。因此，可能干扰 CRF 受体结合的新分子可能对治疗神经精神应激相关疾病有价值。此外，CRF1R 拮抗剂最近已成为先天性肾上腺增生症的潜在治疗选择。此前，我们课题组已开发了多个系列的CRF1受体拮抗剂。为了继续我们在这个方向上的努力，我们在此报告了一系列新的 CRF1R 拮抗剂的合成和生物学评价。与安塔拉明相比，评估了代表性化合物的结合亲和力。四种化合物（2、5、20 和 21）的 log IC50 值分别为 -8.22、-7.95、-8.04 和 -7.88，而安塔拉明的 log IC50 值为 -7.78。该结果表明这四种化合物分别优于antalarmin 2.5、1.4、1.7和1.25倍。值得一提的
• Thiazolo[4,5-d]pyrimidine thiones and -ones as corticotropin-releasing hormone (CRH-R1) receptor antagonists
  作者：James P. Beck、Matt A. Curry、Robert J. Chorvat、Larry W. Fitzgerald、Paul J. Gilligan、Robert Zaczek、George L. Trainor

  DOI：10.1016/s0960-894x(99)00159-6

  日期：1999.4

  A series of thiazolo[4,5-d]pyrimidine thiones and -ones was prepared and discovered to have good binding affinity to the CRH-R1 receptor, thus showing promise as a new class of potential anxiolytics and/or antidepressants. (C) 1999 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.