11α,17α-dihydroxy-5β-pregnane-3,20-dione | 74263-43-7

• 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: 11α,17α-dihydroxy-5β-pregnane-3,20-dione
• 英文别名: 11α,17-dihydroxy-5β-pregnane-3,20-dione；11α,17-Dihydroxy-5β-pregnan-3,20-dion；11α,17α-dihydroxy-5β-pregnan-3,20-dione；(5R,8S,9S,10S,11R,13S,14S,17R)-17-acetyl-11,17-dihydroxy-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 74263-43-7
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: PSGMYFWTNUYMPH-RPRDDUPSSA-N

物化性质

• 熔点：
  191.5-192.5 °C
• 沸点：
  503.4±50.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11α,17α-dihydroxy-5β-pregnane-3,20-dione 在 吡啶 、 semicarbazone 、 溴 作用下， 生成 11α-acetoxy-17-hydroxy-pregn-4-ene-3,20-dione
  参考文献：
  名称：

  11-Oxygenated Steroids. VI. The Synthesis of Δ⁴-Pregnen-11α,17α-diol-3,20-dione (11α, 17α-Dihydroxyprogesterone) and Δ⁴-Pregnen-11α,17α,21-triol-3,20-dione 11-Acetate (11-Epi-Compound F 11-Acetate)^1,2

  摘要：

  DOI：

  10.1021/ja01111a013
• 作为产物：
  描述：

  11Alpha-孕酮 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 氧气 、 sodium hydride 、 对甲苯磺酸 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 、 mineral oil 、 叔丁醇 为溶剂， 反应 70.0h， 生成 11α,17α-dihydroxy-5β-pregnane-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。
• 11-Oxygenated Steroids. V. The Preparation of 11α-Hydroxypregnanes¹
  作者：Eugene P. Oliveto、Hershel L. Herzog、E. B. Hershberg

  DOI：10.1021/ja01102a527

  日期：1953.3
• DE946538
  申请人：——

  公开号：——

  公开（公告）日：——
• Oxidation of 3-hydroxysteroids
  申请人：UPJOHN CO

  公开号：US02714599A1

  公开（公告）日：1955-08-02