(6aR,6bS,8aS,12aS,12bR)-10-amino-6a,8a-dimethyl-4-oxo-2,4,5,6,6a,6b,7,8,8a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]thiophene-9-carbonitrile | 1616254-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (6aR,6bS,8aS,12aS,12bR)-10-amino-6a,8a-dimethyl-4-oxo-2,4,5,6,6a,6b,7,8,8a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]thiophene-9-carbonitrile
• 英文别名: (1R,2S,9S,12S,13R)-6-amino-9,13-dimethyl-16-oxo-5-thiapentacyclo[10.8.0.02,9.04,8.013,18]icosa-4(8),6,17-triene-7-carbonitrile
• CAS: 1616254-86-4
• 化学式: C₂₂H₂₆N₂OS
• 分子量: 366.527
• InChiKey: CLFDBKMFPIPNFI-DJSHNRDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  95.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6aR,6bS,8aS,12aS,12bR)-10-amino-6a,8a-dimethyl-4-oxo-2,4,5,6,6a,6b,7,8,8a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]thiophene-9-carbonitrile 在 盐酸 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 N-((6aR,6bS,8aS,12aS,12bR)-9-cyano-6a,8a-dimethyl-4-oxo-2,4,5,6,6a,6b,7,8,8a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]thiophen-10-yl)-3-oxo-2-(2-phenylhydrazono)butanamide
  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：

  雄烯二酮 、 丙二腈 在 sulfur 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 (6aR,6bS,8aS,12aS,12bR)-10-amino-6a,8a-dimethyl-4-oxo-2,4,5,6,6a,6b,7,8,8a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[2,1-b]thiophene-9-carbonitrile
  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.