2-((6bS,8aS,12aS,12bR)-4-hydroxy-8a-methyl-2,6b,7,8,8a,12,12a,12b-octahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]thiazol-10-yl)acetonitrile | 1609474-81-8

• 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: 2-((6bS,8aS,12aS,12bR)-4-hydroxy-8a-methyl-2,6b,7,8,8a,12,12a,12b-octahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]thiazol-10-yl)acetonitrile
• 英文别名: 2-(4-hydroxy-8a-methyl-2,6b,7,8,8a,12,12a,12b-octahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]thiazol-10-yl)acetonitrile；2-[(1R,2S,9S,12S)-16-hydroxy-9-methyl-5-thia-7-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-4(8),6,13(18),14,16-pentaen-6-yl]acetonitrile
• CAS: 1609474-81-8
• 化学式: C₂₁H₂₂N₂OS
• 分子量: 350.484
• InChiKey: DXTHQJQOYXLBSI-VWXURSGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  85.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((6bS,8aS,12aS,12bR)-4-hydroxy-8a-methyl-2,6b,7,8,8a,12,12a,12b-octahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]thiazol-10-yl)acetonitrile 、 氯化重氮苯 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (6bS,8aS,12aS,12bR,Z)-4-hydroxy-8a-methyl-N'-phenyl-2,6b,7,8,8a,12,12a,12b-octahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]triazole-10-carbohydrazonoyl cyanide
  参考文献：
  名称：

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

  摘要：

  The one pot reaction of estrone with the aromatic aldehydes 2a-c and either of malononitrile or ethyl cyanoacetate afforded the fused pyran derivatives 4a-f. On the other hand, carrying the same reaction using thiourea instead of the cyanomethylene reagent gave the fused pyrimidine derivatives 6a-c. The latter compounds reacted with phenacyl bromide to give the thiazolo[3,2-a]pyrimidine derivatives 8a-c. The reaction of the title compound with bromine gave the monobromo derivative 13 which in turn reacted with either thiourea or cyanothioacetamide to give the thiazole derivatives 14 and 16, respectively. The cytotoxicity of the newly synthesized products was evaluated against six human cancer and normal cell lines where the results showed that compounds 4c, 4f, 6b, 8b, 8c, 10, 13, 16, 18c and 19c exhibited optimal cytotoxic effect against the cancer cell lines, with IC50's in the nM range. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.03.012
• 作为产物：
  描述：

  雌酚酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 2-((6bS,8aS,12aS,12bR)-4-hydroxy-8a-methyl-2,6b,7,8,8a,12,12a,12b-octahydro-1H-naphtho[2',1':4,5]indeno[1,2-d]thiazol-10-yl)acetonitrile
  参考文献：
  名称：

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

  摘要：

  The one pot reaction of estrone with the aromatic aldehydes 2a-c and either of malononitrile or ethyl cyanoacetate afforded the fused pyran derivatives 4a-f. On the other hand, carrying the same reaction using thiourea instead of the cyanomethylene reagent gave the fused pyrimidine derivatives 6a-c. The latter compounds reacted with phenacyl bromide to give the thiazolo[3,2-a]pyrimidine derivatives 8a-c. The reaction of the title compound with bromine gave the monobromo derivative 13 which in turn reacted with either thiourea or cyanothioacetamide to give the thiazole derivatives 14 and 16, respectively. The cytotoxicity of the newly synthesized products was evaluated against six human cancer and normal cell lines where the results showed that compounds 4c, 4f, 6b, 8b, 8c, 10, 13, 16, 18c and 19c exhibited optimal cytotoxic effect against the cancer cell lines, with IC50's in the nM range. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2014.03.012

文献信息

• Synthesis and cytotoxic evaluation of novel hybrid estrane heterocycles as chemotherapeutic anti-cancer agents
  作者：Doaa S. Nada、Dina S Elkady、Ghada H. Elsayed、Adel A.-H. Abdel-Rahman、Gamal A. Elmegeed

  DOI：10.1016/j.steroids.2021.108813

  日期：2021.5