Acetic acid (3S,8R,9S,10R,13S,14S)-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester | 146863-67-4

• 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: Acetic acid (3S,8R,9S,10R,13S,14S)-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
• 英文别名: [(3S,8R,9S,10R,13S,14S)-7-bromo-10,13-dimethyl-17-oxo-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 146863-67-4
• 化学式: C₂₁H₂₉BrO₃
• 分子量: 409.363
• InChiKey: ZYYMXYFTPPZHCY-HNIIPXOESA-N

物化性质

• 沸点：
  468.6±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,8R,9S,10R,13S,14S)-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 在 silver(I) acetate 、 sodium carbonate 、 溶剂黄146 、 lithium bromide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 1.25h， 生成 7-羟基去氢表雄酮
  参考文献：
  名称：

  Ergosteroids II: Biologically Active Metabolites and Synthetic Derivatives of Dehydroepiandrosterone 11This work was supported by Humanetics Corp., St. Louis Park, Minnesota.

  摘要：

  An improved procedure for the synthesis of 3 beta-hydroxyandrost-5-ene-7, 17-dione, a natural metabolite of dehydroepiandrosterone (DHEA) is described. The synthesis and magnetic resonance spectra of several other related steroids are presented. Feeding dehydroepiandrosterone to rats induces enhanced formation of several liver enzymes among which are mitochondrial sn-glycerol 3-phosphate dehydrogenase (GPDH) and cytosolic malic enzyme. The induction of these two enzymes, that complete a thermogenic system in rat liver, was used as an assay to search for derivatives of DHEA that might be more active than the parent steroid. Activity is retained in steroids that are reduced to the corresponding 17 beta-hydroxy derivative, or hydroxylated at 7 alpha or 7 beta, and is considerably enhanced when the 17-hydroxy or 17-carbonyl steroid is converted to the 7-oxo derivative. Several derivatives of DHEA did not induce the thermogenic enzymes whereas the corresponding 7-oxo compounds did. Both short and long chain acyl esters of DHEA and of 7-oxo-DHEA are active inducers of the liver enzymes when fed to rats. 7-Oxo-DHEA-3-sulfate is as active as 7-oxo-DHEA or its 3-acetyl ester, whereas DHEA-3-sulfate is much less active than DHEA. Among many steroids tested, those posessing a carbonyl group at position 3, a methyl group at 7, a hydroxyl group at positions 1, 2, 4, 11, or 19, or a saturated B ring, with or without a 4-5 double bond, were inactive. (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00159-1
• 作为产物：
  描述：

  醋酸去氢表雄酮 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 环己烷 为溶剂， 反应 1.83h， 生成 Acetic acid (3S,8R,9S,10R,13S,14S)-7-bromo-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  具有杂化侧链作为抗癌剂的新型5α，8α-内过氧化物甾体衍生物的设计，合成和生物学评估。

  摘要：

  合成并表征了一系列新颖的5α，8α-内过氧化物甾体杂化衍生物，其在C-17侧链上含有isatin或吲哚取代基。研究了该化合物对HepG2，MCF-7，HT-29和HeLa细胞系的初步抗增殖活性。化合物7g和7l在体外对HepG2和Hela细胞显示出显着的抗增殖活性，IC50值低于8μM。此外，通过流式细胞术和菌落分析检查了7g的生物学功能。结果表明7g可以诱导HepG2细胞凋亡，抑制细胞周期进程和集落生长。研究表明，C-17位的结构修饰可能是设计类固醇抗癌药的有希望的起点。

  DOI：

  10.1016/j.steroids.2019.108471

文献信息

• Design, synthesis and biological evaluation of novel 5α, 8α-endoperoxide steroidal derivatives with hybrid side chain as anticancer agents
  作者：Hongling Li、Haijun Wang、Jing Wang、Yu Lin、Yukun Ma、Ming Bu

  DOI：10.1016/j.steroids.2019.108471

  日期：2020.1

  A series of novel 5α, 8α-endoperoxide steroidal hybrid derivatives containing isatin or indole substituents on the C-17 side chain were synthesized and characterized. The preliminary anti-proliferative activity of the compounds against HepG2, MCF-7, HT-29 and HeLa cell lines were investigated. Compounds 7g and 7l displayed significant anti-proliferative activity in vitro against HepG2 and Hela cells

  合成并表征了一系列新颖的5α，8α-内过氧化物甾体杂化衍生物，其在C-17侧链上含有isatin或吲哚取代基。研究了该化合物对HepG2，MCF-7，HT-29和HeLa细胞系的初步抗增殖活性。化合物7g和7l在体外对HepG2和Hela细胞显示出显着的抗增殖活性，IC50值低于8μM。此外，通过流式细胞术和菌落分析检查了7g的生物学功能。结果表明7g可以诱导HepG2细胞凋亡，抑制细胞周期进程和集落生长。研究表明，C-17位的结构修饰可能是设计类固醇抗癌药的有希望的起点。
• Ergosteroids II: Biologically Active Metabolites and Synthetic Derivatives of Dehydroepiandrosterone 11This work was supported by Humanetics Corp., St. Louis Park, Minnesota.
  作者：Henry Lardy、Nancy Kneer、Yong Wei、Bruce Partridge、Padma Marwah

  DOI：10.1016/s0039-128x(97)00159-1

  日期：1998.3

  An improved procedure for the synthesis of 3 beta-hydroxyandrost-5-ene-7, 17-dione, a natural metabolite of dehydroepiandrosterone (DHEA) is described. The synthesis and magnetic resonance spectra of several other related steroids are presented. Feeding dehydroepiandrosterone to rats induces enhanced formation of several liver enzymes among which are mitochondrial sn-glycerol 3-phosphate dehydrogenase (GPDH) and cytosolic malic enzyme. The induction of these two enzymes, that complete a thermogenic system in rat liver, was used as an assay to search for derivatives of DHEA that might be more active than the parent steroid. Activity is retained in steroids that are reduced to the corresponding 17 beta-hydroxy derivative, or hydroxylated at 7 alpha or 7 beta, and is considerably enhanced when the 17-hydroxy or 17-carbonyl steroid is converted to the 7-oxo derivative. Several derivatives of DHEA did not induce the thermogenic enzymes whereas the corresponding 7-oxo compounds did. Both short and long chain acyl esters of DHEA and of 7-oxo-DHEA are active inducers of the liver enzymes when fed to rats. 7-Oxo-DHEA-3-sulfate is as active as 7-oxo-DHEA or its 3-acetyl ester, whereas DHEA-3-sulfate is much less active than DHEA. Among many steroids tested, those posessing a carbonyl group at position 3, a methyl group at 7, a hydroxyl group at positions 1, 2, 4, 11, or 19, or a saturated B ring, with or without a 4-5 double bond, were inactive. (C) 1998 by Elsevier Science Inc.