21-O-[2’(RS)]tetrahydropyranyloxypregn-4-ene-3,20-dione | 492453-63-1

• 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: 21-O-[2’(RS)]tetrahydropyranyloxypregn-4-ene-3,20-dione
• 英文别名: 4-pregnen-21-ol-3,20-dione 21-(2'-tetrahydropyranyl)ether；21-((Ξ)-tetrahydropyran-2-yloxy)-pregn-4-ene-3,20-dione；21-((Ξ)-Tetrahydropyran-2-yloxy)-pregn-4-en-3,20-dion；(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-[2-(oxan-2-yloxy)acetyl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 492453-63-1
• 化学式: C₂₆H₃₈O₄
• 分子量: 414.585
• InChiKey: HJBFKCBQEVRXLS-CHZCGKKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  21-O-[2’(RS)]tetrahydropyranyloxypregn-4-ene-3,20-dione 在 氢氧化钾 、 sodium hydroxide 、 双氧水 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 8.0h， 生成 4-(2-carboxyethylthio)-11-deoxycorticosterone
  参考文献：
  名称：

  A radioimmunoassay for deoxycorticosterone sulfate without hydrolysis

  摘要：

  The hapten of deoxycorticosterone sulfate was synthesized and linked to the carrier protein through the C-4 position on the steroid nucleus. The antisera raised against this antigen in guinea pigs exhibited high affinity (Ka = 1.86 x 10(9) M-1) and excellent specificity for deoxycorticosterone sulfate. It was found that deoxycorticosterone sulfate can be determined in the range of 50-5000 pg, and this radioimmunoassay in plasma shows a coefficient of variation (CV) less than 10%.

  DOI：

  10.1016/0039-128x(87)90092-4
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 去氧皮质酮 在 盐酸 、 乙醚 作用下， 生成 21-O-[2’(RS)]tetrahydropyranyloxypregn-4-ene-3,20-dione
  参考文献：
  名称：

  The Reaction of Dihydropyran with Steroidal Alcohols. Utility in the Syntheses of Testosterone Acyl Esters¹

  摘要：

  DOI：

  10.1021/ja01125a029

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。
• Synthesis of New Steroidal Inhibitors of P-Glycoprotein-Mediated Multidrug Resistance and Biological Evaluation on K562/R7 Erythroleukemia Cells
  作者：Marc Rolland de Ravel、Ghina Alameh、Maxime Melikian、Zahia Mahiout、Agnès Emptoz-Bonneton、Eva-Laure Matera、Thierry Lomberget、Roland Barret、Luc Rocheblave、Nadia Walchshofer、Sonia Beltran、Lucienne El Jawad、Elisabeth Mappus、Catherine Grenot、Michel Pugeat、Charles Dumontet、Marc Le Borgne、Claude Yves Cuilleron

  DOI：10.1021/jm501676v

  日期：2015.2.26

  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.
• Steroids. LXXXII.¹ Synthesis of 4-Halo Hormone Analogs
  作者：H. J. RINGOLD、E. BATRES、O. MANCERA、G. ROSENKRANZ

  DOI：10.1021/jo01118a028

  日期：1956.12.1
• The Reaction of Dihydropyran with Steroidal Alcohols. Utility in the Syntheses of Testosterone Acyl Esters¹
  作者：Arnold C. Ott、Maxton F. Murray、Raymond L. Pederson

  DOI：10.1021/ja01125a029

  日期：1952.3