5β-17α-hydroxy-preganene-3,20-dione | 570-58-1

• 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: 5β-17α-hydroxy-preganene-3,20-dione
• 英文别名: 17α-hydroxy-5β-pregnan-3,20-dione；5β-pregnan-17α-ol-3,20-dione；17-hydroxy-5β-pregnane-3,20-dione；17-Hydroxy-5β-pregnan-3,20-dion；5-β-pregnan-17-ol-3,20-dione；17α-Hydroxy-5β-pregnan-3,20-dion；(5S,8R,9S,10S,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyltetradecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one；(5R,8R,9S,10S,13S,14S,17R)-17-acetyl-17-hydroxy-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 570-58-1
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: UUOHXXXJRQGPLC-QCQJMWNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.904
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5β-17α-hydroxy-preganene-3,20-dione 在 高氯酸 、 dipyridine chromium trioxide 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 醋羟孕酮
  参考文献：
  名称：

  Hernandez, J. Edgardo; Samano, Vicente; Valdes, Victoria, Synthetic Communications, 1990, vol. 20, # 1, p. 131 - 136

  摘要：

  DOI：
• 作为产物：
  描述：

  17Alpha-羟基黄体酮 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 17.0h， 以77%的产率得到5β-17α-hydroxy-preganene-3,20-dione
  参考文献：
  名称：

  Synthesis of New Steroidal Inhibitors of P-Glycoprotein-Mediated Multidrug Resistance and Biological Evaluation on K562/R7 Erythroleukemia Cells

  摘要：

  A simple route for improving the potency of progesterone as a modulator of P-gp-mediated multidrug resistance was established by esterification or etherification of hydroxylated 5 alpha/beta-pregnane-3,20-dione or 5 beta-cholan-3-one precursors. X-ray crystallography of representative 7 alpha-, 11 alpha-, and 17 alpha-(2'R/S)-O-tetrahydropyranyl ether diastereoisomers revealed different combinations of axial-equatorial configurations of the anomeric oxygen. Substantial stimulation of accumulation and chemosensitization was observed on K562/R7 erythroleukemia cells resistant to doxorubicin, especially using 7 alpha,11 alpha-O-disubstituted derivatives of 5 alpha/beta-pregnane-3,20-dione, among which the 5 beta-H-7 alpha-benzoyloxy-11 alpha-(2'R)-O-tetrahydropyranyl ether 22a revealed promising properties (accumulation index 2.9, IC50 0.5 mu M versus 1.2 and 10.6 mu M for progesterone), slightly overcoming those of verapamil and cyclosporin A. Several 7 alpha,12 alpha-O-disubstituted derivatives of 5 beta-cholan-3-one proved even more active, especially the 7 alpha-O-methoxymethyl-12 alpha-benzoate 56 (accumulation index 3.8, IC50 0.2 mu M). The panel of modulating effects from different O-substitutions at a same position suggests a structural influence of the substituent completing a simple protection against stimulating effects of hydroxyl groups on P-gp-mediated transport.

  DOI：

  10.1021/jm501676v

文献信息

• [EN] NEW STEROID INHIBITORS OF PGP FOR USE FOR INHIBITING MULTIDRUG RESISTANCE<br/>[FR] NOUVEAUX INHIBITEURS STÉROÏDIENS DE PGP POUR EMPLOI DANS L'INHIBITION DE LA RÉSISTANCE PLÉIOTROPE
  申请人：INST NAT SANTE RECH MED

  公开号：WO2011073419A1

  公开（公告）日：2011-06-23

  The present invention relates to a compound of formula (I) for its use for reversing or inhibiting multidrug resistance.

  本发明涉及一种化合物，其化学式为(I)，用于逆转或抑制多药耐药。
• NEW STEROID INHIBITORS OF PGP FOR USE FOR INHIBITING MULTIDRUG RESISTANCE
  申请人：Grenot Catherine

  公开号：US20120309728A1

  公开（公告）日：2012-12-06

  The present invention relates to a compound of formula (I) for its use for reversing or inhibiting multidrug resistance.

  本发明涉及一种式（I）的化合物，用于逆转或抑制多药耐药。
• Steroids. XLIII.¹ A Ten Step Conversion of Progesterone to Cortisone. The Differential Reduction of Pregnane-3,20-diones with Sodium Borohydride²
  作者：O. Mancera、Howard J. Ringold、Carl Djerassi、G. Rosenkranz、Franz Sondheimer

  DOI：10.1021/ja01102a006

  日期：1953.3
• Partial Synthesis of Compounds Related to Adrenal Cortical Hormones. XIV. Preparation of the Dihydroxyacetone Side Chain; 17α-Hydroxyprogesterone and “Substances L and P”¹
  作者：Theodore H. Kritchevsky、T. F. Gallagher

  DOI：10.1021/ja01145a064

  日期：1951.1
• Kritchevsky; Gallagher, Journal of Biological Chemistry, 1949, vol. 179, p. 507,508
  作者：Kritchevsky、Gallagher

  DOI：——

  日期：——