(E)-cholest-4-en-6-one oxime | 110612-22-1

• 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: (E)-cholest-4-en-6-one oxime
• 英文别名: (NE)-N-[(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-ylidene]hydroxylamine
• CAS: 110612-22-1
• 化学式: C₂₇H₄₅NO
• 分子量: 399.66
• InChiKey: IGFLSVGQDROTSC-ARPPVSAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.4
• 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：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-cholest-4-en-6-one oxime 在 盐酸 、 sodium hydroxide 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 2.03h， 生成 B-homo-6-azacholest-4-en-7-one
  参考文献：
  名称：

  Anastasia, Mario; Allevi, Pietro; Ciuffreda, Pierangela, Journal of the Chemical Society. Perkin transactions I, 1986, p. 2123 - 2126

  摘要：

  DOI：
• 作为产物：
  描述：

  胆固醇-5Alpha,6Alpha-环氧化物 在 吡啶 、 盐酸羟胺 、 magnesium bromide 作用下， 以 乙醚 、 苯 为溶剂， 反应 20.5h， 生成 (E)-cholest-4-en-6-one oxime
  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

• 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.