B-homo-6-azacholest-4-en-7-one | 110556-52-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: B-homo-6-azacholest-4-en-7-one
• 英文别名: 6-aza-B-homocholest-4-en-7-one；(1S,2R,11S,12S,15R,16R)-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-azatetracyclo[9.7.0.02,7.012,16]octadec-6-en-9-one
• CAS: 110556-52-0
• 化学式: C₂₇H₄₅NO
• 分子量: 399.66
• InChiKey: SXZUBDQJERSSJL-VHHOZFFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  B-homo-6-azacholest-4-en-7-one 在 劳森试剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以78.75%的产率得到6-aza-7-thioxo-B-homocholest-4-ene
  参考文献：
  名称：

  Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities

  摘要：

  The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.02.005
• 作为产物：
  描述：

  胆固醇-5Alpha,6Alpha-环氧化物 在 吡啶 、 盐酸羟胺 、 magnesium bromide 、 三氯氧磷 作用下， 以 乙醚 、 苯 为溶剂， 反应 24.5h， 生成 B-homo-6-azacholest-4-en-7-one
  参考文献：
  名称：

  Suginome, Hiroshi; Ohshima, Koji; Ohue, Yoshihiko, Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3239 - 3250

  摘要：

  DOI：

文献信息

• Anastasia, Mario; Allevi, Pietro; Ciuffreda, Pierangela, Journal of the Chemical Society. Perkin transactions I, 1986, p. 2123 - 2126
  作者：Anastasia, Mario、Allevi, Pietro、Ciuffreda, Pierangela、Fiecchi, Alberto、Scala, Antonio

  DOI：——

  日期：——
• Suginome, Hiroshi; Ohshima, Koji; Ohue, Yoshihiko, Journal of the Chemical Society. Perkin transactions I, 1994, # 21, p. 3239 - 3250
  作者：Suginome, Hiroshi、Ohshima, Koji、Ohue, Yoshihiko、Ohki, Takashi、Senboku, Hisanori

  DOI：——

  日期：——
• Synthesis of some steroidal oximes, lactams, thiolactams and their antitumor activities
  作者：Natalija M. Krstić、Mira S. Bjelaković、Željko Žižak、Mirjana D. Pavlović、Zorica D. Juranić、Vladimir D. Pavlović

  DOI：10.1016/j.steroids.2007.02.005

  日期：2007.5

  The antiproliferative activity of previously synthesized (Z)-cholest-4-en-6-one oxime (1), (E)-cholest-4-en-6-one oxime (2), 7-aza-B-homocholest-4-en-6-one (3) and 6-aza-B-homocholest-4-en-7-one (4) and newly synthesized 6-thioxo-7-aza-B-homocholest-4-ene (5) and 6-aza-7-thioxo-B-homocholest-4-ene (6) was tested for their possible effects against two human tumor cell lines, cervical carcinoma (HeLa) and chronic myelogenous leukemia (K-562). Compounds 1-6, exerted a dose-dependent antiproliferative effect toward cell lines used in experimental design, showing high selectivity in their action for tumor cells in comparison to normal immunocompetent cells (non-stimulated PBMC and PHA-stimulated PBMC). Compounds 2, 3 and 4 exhibited a very high but selective antitumor activity, by inducing apoptosis in sensitive, for that purpose targeted tumor cell line (HeLa cells). Low toxic effect upon both non-stimulated, and PHA stimulated PBMCs from control, healthy volunteers, has been detected for compounds 1, 2, 3 and 4. The possible reasons for profound differences in the effects of this spectrum of steroidal compounds between tumor cell lines and normal stimulated and non-stimulated PBMCs are discussed. The molecular mechanisms for apoptotic events in HeLa cell line are suggested. The guidelines for further research are underlined. (c) 2007 Elsevier Inc. All rights reserved.