7β-acetylcholesterol | 17974-78-6

• 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: 7β-acetylcholesterol
• 英文别名: 3β-hydroxycholest-5-en-7β-yl acetate；acetic acid-(3β-hydroxy-cholesten-(5)-yl-(7β)-ester)；Essigsaeure-(3β-hydroxy-cholesten-(5)-yl-(7β)-ester)；(10R)-3c-Hydroxy-7c-acetoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren；7β-Acetoxy-cholesten-(5)-ol-(3β)；[(3S,7R,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-7-yl] acetate
• CAS: 17974-78-6
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: MMIBWYWPPODERI-NHGCSETBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7β-acetylcholesterol 生成 7β-acetylcholesteryl benzoate
  参考文献：
  名称：

  363. 甾醇组的研究。L 部分：7-取代的胆固醇衍生物及其立体化学（第 III 部分）。7-烷氧基胆固醇衍生物

  摘要：

  DOI：

  10.1039/jr9480001798
• 作为产物：
  描述：

  7β-acetylcholesteryl benzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 7β-acetylcholesterol
  参考文献：
  名称：

  [EN] STEROL DERIVATIVES AND USE THEREOF FOR TREATING DISEASES INVOLVING TRANSFORMED ASTROCYTE CELLS OR FOR TREATING MALIGNANT HAEMOPATHIES
  [FR] DÉRIVÉS DE STÉROL ET LEUR UTILISATION DANS LE TRAITEMENT DE MALADIES IMPLIQUANT DES CELLULES ASTROCYTES TRANSFORMÉES OU DANS LE TRAITEMENT D'HÉMOPATHIES MALIGNES

  摘要：

  本发明涉及新型甾醇衍生物、其制备方法、含有它们的药物组合物以及用于治疗涉及转化星形胶质细胞或治疗恶性血液病的用途。本发明特别涉及治疗多形性胶质母细胞瘤以及其他癌症，如淋巴瘤、神经母细胞瘤和黑色素瘤。

  公开号：

  WO2013168096A1

文献信息

• Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption
  作者：Samuel D. Offei、Hadi D. Arman、Francis K. Yoshimoto

  DOI：10.1016/j.steroids.2019.108449

  日期：2019.11

  syndrome, and other diseases associated with defective bile acid biosynthesis. Furthermore, 7α-hydroxy-cholest-4-en-3-one is the physiological substrate for cytochrome P450 8B1 (P450 8B1 or CYP8B1), the oxysterol 12α-hydroxylase enzyme implicated in obesity and cardiovascular health. We report the chemical synthesis of this physiologically important oxysterol beginning with cholesterol. The key feature

  7α-Hydroxy-cholest-4-en-3-one是胆汁酸流失，肠易激综合征和其他与胆汁酸生物合成缺陷有关的疾病的生物标志物。此外，7α-羟基胆甾醇4-en-3-one是细胞色素P450 8B1（P450 8B1或CYP8B1）的生理底物，P450 8B1或CYP8B1是与肥胖症和心血管健康有关的氧固醇12α-羟化酶。我们从胆固醇开始报告了这种具有重要生理意义的氧固醇的化学合成。该合成的关键特征涉及3-脱氧-Δ4-7α-甲酸酯类固醇前体的区域选择性C3-烯丙基氧化形成7α-甲氧基-胆甾醇4-en-3-one，将其皂化生成7α-羟基-cholest-4-en-3-one。
• Stary, Ivo; Kocovsky, Pavel, Collection of Czechoslovak Chemical Communications, 1985, vol. 50, # 5, p. 1227 - 1238
  作者：Stary, Ivo、Kocovsky, Pavel

  DOI：——

  日期：——
• Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm200803d

  日期：2011.9.22

  Chemically diverse oxysterols were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against seven cancer (HT-29, HepG2, A549, PC3, LAMA-84, MCF-7, and SH-SYSY) and two noncancerous cell lines (ARPE-19 and BJ). The influence of the oxidation pattern on rings A and B was studied. Oxygen functionalities on ring B, such as oxo, oxime, acetamide, acetate, and alkoxy, were evaluated. Most oxysterols were cytotoxic in the low micromolar range, with emphasis to the tetrols 14 and 34, the 6 beta methoxy and acetoxy derivatives 21 and 45, and the oxime 28. In general, the oxysterols were more toxic to cancer cells and a set of compounds (9, 14, 21, 28, 45) with very high selectivity was identified. The cytotoxicity of 3 beta-acetates was lower than that of the parent alcohols, although incubation for a longer period rendered them equally cytotoxic, pointing them as potential prodrugs of oxysterols.