(6aR,6bS,8aS,13aS,13bR)-10-mercapto-6a,8a-dimethyl-12-(pyridin-3-yl)-5,6,6a,6b,7,8,8a,9,12,13,13a,13b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]pyrimidin-4(2H)-one | 1616254-80-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (6aR,6bS,8aS,13aS,13bR)-10-mercapto-6a,8a-dimethyl-12-(pyridin-3-yl)-5,6,6a,6b,7,8,8a,9,12,13,13a,13b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]pyrimidin-4(2H)-one
• 英文别名: (1R,2S,10S,13S,14R)-10,14-dimethyl-5-pyridin-3-yl-7-sulfanylidene-6,8-diazapentacyclo[11.8.0.02,10.04,9.014,19]henicosa-4(9),18-dien-17-one
• CAS: 1616254-80-8
• 化学式: C₂₆H₃₁N₃OS
• 分子量: 433.618
• InChiKey: BBOPGVFMXSTOMA-DUCCTLTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  86.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6aR,6bS,8aS,13aS,13bR)-10-mercapto-6a,8a-dimethyl-12-(pyridin-3-yl)-5,6,6a,6b,7,8,8a,9,12,13,13a,13b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]pyrimidin-4(2H)-one 、 2-溴-4'-甲基苯乙酮 以 乙醇 为溶剂， 反应 1.0h， 生成 (6aR,6bS,8aS,15aS,15bR)-6a,8a-dimethyl-14-(pyridin-3-yl)-10-(p-tolyl)-1,5,6,6a,6b,7,8,8a,14,15,15a,15b-dodecahydronaphtho[2',1':4,5]indeno[2,1-e]thiazolo[3,2-a]pyrimidin-4(2H)-one
  参考文献：
  名称：

  Heterocyclic ring extension of androstenedione: Synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives

  摘要：

  The reaction of androstenedione with either malononitrile or ethyl cyanoacetate and aromatic aldehydes 2a-c gave the pyran derivatives 4a-f, respectively. On the other hand, the reaction of androstenedione with thiourea and the aromatic aldehydes 2a-c gave the pyrimidine derivatives 6a-c, respectively. Compound 6b reacted with 2-bromo-1-arylethanone derivatives 7a-d to give the indeno[2,1-e]thiazole derivatives 8a-d. Some of the produced compounds were used for further heterocyclization reactions. The cytotoxicity of the newly obtained products was evaluated against some cancer cell lines and a normal cell line. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.04.011
• 作为产物：
  描述：

  3-吡啶甲醛 、 雄烯二酮 、 硫脲 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (6aR,6bS,8aS,13aS,13bR)-10-mercapto-6a,8a-dimethyl-12-(pyridin-3-yl)-5,6,6a,6b,7,8,8a,9,12,13,13a,13b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]pyrimidin-4(2H)-one
  参考文献：
  名称：

  Heterocyclic ring extension of androstenedione: Synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives

  摘要：

  The reaction of androstenedione with either malononitrile or ethyl cyanoacetate and aromatic aldehydes 2a-c gave the pyran derivatives 4a-f, respectively. On the other hand, the reaction of androstenedione with thiourea and the aromatic aldehydes 2a-c gave the pyrimidine derivatives 6a-c, respectively. Compound 6b reacted with 2-bromo-1-arylethanone derivatives 7a-d to give the indeno[2,1-e]thiazole derivatives 8a-d. Some of the produced compounds were used for further heterocyclization reactions. The cytotoxicity of the newly obtained products was evaluated against some cancer cell lines and a normal cell line. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.04.011

文献信息

• Heterocyclic ring extension of androstenedione: Synthesis and cytotoxicity of fused pyran, pyrimidine and thiazole derivatives
  作者：Rafat M. Mohareb、Nermeen S. Abbas、Mahmoud A. Abdelaziz

  DOI：10.1016/j.steroids.2014.04.011

  日期：2014.8

  The reaction of androstenedione with either malononitrile or ethyl cyanoacetate and aromatic aldehydes 2a-c gave the pyran derivatives 4a-f, respectively. On the other hand, the reaction of androstenedione with thiourea and the aromatic aldehydes 2a-c gave the pyrimidine derivatives 6a-c, respectively. Compound 6b reacted with 2-bromo-1-arylethanone derivatives 7a-d to give the indeno[2,1-e]thiazole derivatives 8a-d. Some of the produced compounds were used for further heterocyclization reactions. The cytotoxicity of the newly obtained products was evaluated against some cancer cell lines and a normal cell line. (C) 2014 Elsevier Inc. All rights reserved.