3-oxo-4-aza-7'-(4-morpholinylphenyl)-5α-androstano[17,16-d][1,2,4]triazolo[1,5-a]pyrimidine | 1369581-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-oxo-4-aza-7'-(4-morpholinylphenyl)-5α-androstano[17,16-d][1,2,4]triazolo[1,5-a]pyrimidine
• 英文别名: (1S,2R,5R,10R,11S,14S)-10,14-dimethyl-22-(4-morpholin-4-ylphenyl)-6,16,18,20,21-pentazahexacyclo[12.10.0.02,11.05,10.015,23.017,21]tetracosa-15,17,19,22-tetraen-7-one
• CAS: 1369581-63-4
• 化学式: C₃₁H₃₈N₆O₂
• 分子量: 526.682
• InChiKey: BRQOAOVRVIFOBZ-WPGJGDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  39
• 可旋转键数：
  2
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  84.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(4-吗啉)苯甲醛 、 4-aza-5α-androstane-3,17-dione 在 potassium tert-butylate 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 31.0h， 生成 3-oxo-4-aza-7'-(4-morpholinylphenyl)-5α-androstano[17,16-d][1,2,4]triazolo[1,5-a]pyrimidine
  参考文献：
  名称：

  Synthesis of novel D-ring fused 7′-aryl-androstano[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines

  摘要：

  The preparation of novel steroidal heterocycles containing the 7-aryl-substituted 1,2,4-triazolo [1,5-a]pyrimidine moiety fused to the 16,17-positions of the steroid nucleus is described. The Aldol reaction of 4-aza-androst-3,17-dione (la) and dehydroepiandrosterone (DHEA, 1b) with aromatic aldehydes was catalyzed by KF/Al2O3 to give the corresponding 3-oxo-4-aza-5 alpha- and 3 beta-hydroxy-5-en-16-arylidene-17-ketosteroids (2a-r). Subsequently, the intermediates 2a-r reacted with dinucleophilic 3-amino-1,2,4-triazole in presence of t-BuOK to afford the title compounds (3a-r). All the synthesized heterosteroids are new and are currently being evaluated for their biological activities. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.12.012

文献信息

• Synthesis and biological evaluation of novel steroidal[17,16-d][1,2,4]triazolo[1,5-a]pyrimidines
  作者：Li-Hua Huang、Yong-Fei Zheng、Yong-Zheng Lu、Chuan-Jun Song、Yan-Guang Wang、Bin Yu、Hong-Min Liu

  DOI：10.1016/j.steroids.2012.03.002

  日期：2012.5

  The preparation of steroidal[17,16-d][1,2,4]triazolo[1,5-a]pyrimidines and their biological evaluation as potential anticancer agents are herein reported. These novel heterosteroids (2, 4) were prepared through the condensation reaction of 3-amino-1,2,4-triazole with 16-arylidene-17-ketosteroids (1, 3). All the synthesized compounds were evaluated for their anticancer activity in vitro against PC-3 (human prostatic carcinoma), MCF-7 (human breast carcinoma) and EC9706 (human esophageal carcinoma) cell lines. Among the screened compounds, 2i, 2n and 4f showed significant inhibitory activity against all the three human cell lines. (c) 2012 Elsevier Inc. All rights reserved.
• Synthesis of novel D-ring fused 7′-aryl-androstano[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines
  作者：Li-Hua Huang、Yong-Fei Zheng、Chuan-Jun Song、Yan-Guang Wang、Zhi-Yu Xie、Yao-Wen Lai、Yong-Zheng Lu、Hong-Min Liu

  DOI：10.1016/j.steroids.2011.12.012

  日期：2012.4

  The preparation of novel steroidal heterocycles containing the 7-aryl-substituted 1,2,4-triazolo [1,5-a]pyrimidine moiety fused to the 16,17-positions of the steroid nucleus is described. The Aldol reaction of 4-aza-androst-3,17-dione (la) and dehydroepiandrosterone (DHEA, 1b) with aromatic aldehydes was catalyzed by KF/Al2O3 to give the corresponding 3-oxo-4-aza-5 alpha- and 3 beta-hydroxy-5-en-16-arylidene-17-ketosteroids (2a-r). Subsequently, the intermediates 2a-r reacted with dinucleophilic 3-amino-1,2,4-triazole in presence of t-BuOK to afford the title compounds (3a-r). All the synthesized heterosteroids are new and are currently being evaluated for their biological activities. (C) 2011 Elsevier Inc. All rights reserved.