(6aR,6bS,8aS,12aS,12bR)-6a,8a-dimethyl-9-phenyl-10-thioxo-5,6,6a,6b,7,8,8a,9,10,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]thiazol-4(2H)-one | 1616255-02-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6aR,6bS,8aS,12aS,12bR)-6a,8a-dimethyl-9-phenyl-10-thioxo-5,6,6a,6b,7,8,8a,9,10,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]thiazol-4(2H)-one
• 英文别名: (1R,2S,9S,12S,13R)-9,13-dimethyl-7-phenyl-6-sulfanylidene-5-thia-7-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-4(8),17-dien-16-one
• CAS: 1616255-02-7
• 化学式: C₂₆H₂₉NOS₂
• 分子量: 435.654
• InChiKey: CSZMESRXMLBHLE-AQKOAMEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  雄烯二酮 、 硫代异氰酸苯酯 在 sulfur 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 (6aR,6bS,8aS,12aS,12bR)-6a,8a-dimethyl-9-phenyl-10-thioxo-5,6,6a,6b,7,8,8a,9,10,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]thiazol-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.