acetic acid (1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1-(4-hydroxy-4-methylpentyl)-5-methylhexyl]-7a-methyloctahydroinden-4-yl ester | 792959-61-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: acetic acid (1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1-(4-hydroxy-4-methylpentyl)-5-methylhexyl]-7a-methyloctahydroinden-4-yl ester
• 英文别名: [1R,3aR,4S,7aR]-acetic acid 1-[4(R),5-dihydroxy-1(R)-(4-hydroxy-4-methyl-pentyl)-5-methyl-hexyl]-7a-methyl-octahydro-inden-4-yl ester；acetic acid [1R,3aR,4S,7aR]-1-[4(R),5-dihydroxy-1(R)-(4-hydroxy-4-methyl-pentyl)-5-methyl-hexyl]-7a-methyl-octahydro-inden-4-yl ester；[1R,3aR,4S,7aR]-acetic acid 1-[4(R),5-dihydroxy-1(R)-(4-hydroxy-4-methyl-pentyl)-5-methyl-hexyl]-7a-methyl-octahydroinden-4-yl ester；acetic acid [1R,3aR,4S,7aR]-1-[4(R),5-dihydroxy-1(R)-(4-hydroxy-4-methylpentyl)-5-methylhexyl]-7a-methyloctahydroinden-4-yl ester；[1R,3aR,4S,7aR]-Acetic acid 1-[4(R), 5-dihydroxy-1(R)-(4-hydroxy-4-methyl-pentyl)-5-methyl-hexyl]-7a-methyl-octahydro-inden-4-yl ester；[(1R,3aR,4S,7aR)-7a-methyl-1-[(3R,6R)-2,3,10-trihydroxy-2,10-dimethylundecan-6-yl]-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] acetate
• CAS: 792959-61-6
• 化学式: C₂₅H₄₆O₅
• 分子量: 426.637
• InChiKey: ATXMIRMWMFCQAR-KYCKWARNSA-N

物化性质

• 沸点：
  538.7±30.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  acetic acid (1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1-(4-hydroxy-4-methylpentyl)-5-methylhexyl]-7a-methyloctahydroinden-4-yl ester 在 咪唑 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 正丁基锂 、 Celite 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 118.17h， 生成 1,25-dihydroxy-21-(2R,3-dihydroxy-3-methyl-butyl)-20R-cholecalciferol
  参考文献：
  名称：

  Calcitriol Derivatives with Two Different Side Chains at C-20. II. Diastereoselective Syntheses of the Metabolically Produced 24(R)-Hydroxygemini

  摘要：

  Vitamin D derivatives containing two side chains emanating at C-20 are known as gemini. We have recently synthesized two gemini which are related to calcitriol and 19-norcalcitriol containing two identical side chains. The metabolism of these species involves 24(R)hydroxylation on one of the side chains. To determine the outcome of this diastereospecific transformation, we synthesized both C-20 epimeric pairs containing the 24(R)-hydroxy group in the gemini and 19-norgemini series. On the basis of the availability of these reference compounds, it was shown that the metabolic hydroxylation occurred at the pro-R side chain in both gemini compounds. In comparison to the parent compounds, the 24-hydroxygemini required higher doses to increase blood calcium levels in mice and to suppress INF-gamma release in MLR.

  DOI：

  10.1021/jm049340b
• 作为产物：
  描述：

  (R)-6-[(1R,3aR,4S,7aR)-4-(tert-butyldimethylsilanyloxy)-7a-methyloctahydroinden-1-yl]-2-methylnon-8-yn-2-ol 在 吡啶 、 甲醇 、 sodium-mercury amalgam (5%) 、 正丁基锂 、 六氟合硅酸 、 4-甲基苯磺酸吡啶 、 草酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 环己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 83.75h， 生成 acetic acid (1R,3aR,4S,7aR)-1-[(1R,4R)-4,5-dihydroxy-1-(4-hydroxy-4-methylpentyl)-5-methylhexyl]-7a-methyloctahydroinden-4-yl ester
  参考文献：
  名称：

  WO2006/100285

  摘要：

  公开号：

文献信息

• GEMINI VITAMIN D3 COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Adorini Luciano

  公开号：US20080280859A1

  公开（公告）日：2008-11-13

  The invention provides Gemini vitamin D 3 compounds, methods for using the compounds to treat vitamin D3 associated states and pharmaceutical compositions containing the compounds.

  这项发明提供了双子座维生素D3化合物，使用这些化合物治疗与维生素D3相关疾病的方法以及含有这些化合物的药物组合物。
• [EN] USE OF VITAMIN D COMPOUNDS FOR THE PREVENTION OR TREATMENT OF CHRONIC PROSTATITIS<br/>[FR] UTILISATION DE COMPOSES DE VITAMINE D POUR LA PREVENTION OU LE TRAITEMENT DE LA PROSTATITE CHRONIQUE
  申请人：BIOXELL SPA

  公开号：WO2006035075A1

  公开（公告）日：2006-04-06

  The use of a vitamin D compound in the prevention or treatment of chronic prostatitis and related methods, pharmaceutical formulations and kits.

  维生素D化合物在慢性前列腺炎的预防或治疗中的使用，以及相关方法、药物配方和工具包。
• Treatment of Interstitial Cystitis with Vitamin D Compounds
  申请人：Colli Enrico

  公开号：US20080039434A1

  公开（公告）日：2008-02-14

  There is provided according to the invention a vitamin D compound for use in the prevention and/or treatment of interstitial cystitis. Also provided is a method for preventing and/or treating interstitial cystitis by administering an effective amount of a vitamin D compound.

  本发明提供了一种维生素D化合物，用于预防和/或治疗间质性膀胱炎。同时提供了一种方法，通过给予有效剂量的维生素D化合物来预防和/或治疗间质性膀胱炎。
• Use of Vitamin D Compounds to Treat Endometriosis
  申请人：Panina Paola

  公开号：US20080280860A1

  公开（公告）日：2008-11-13

  The use of vitamin D compounds in the treatment or prevention of endometriosis, methods for the treatment or prevention of endometriosis by administering a vitamin D compound, and compounds for use therein.

  维生素D化合物在治疗或预防子宫内膜异位症中的应用，通过给予维生素D化合物治疗或预防子宫内膜异位症的方法，以及用于其中的化合物。
• Methods for treating bladder dysfunction
  申请人：Colli Enrico

  公开号：US20070054887A1

  公开（公告）日：2007-03-08

  There is provided according to the invention the use of Vitamin D compounds such as 1-alpha-fluoro-25-hydroxy-16,23e-diene-26,27-bishomo-20-epi-cholecalciferol in the prevention or treatment of bladder dysfunction.

  本发明提供了使用维生素D类化合物，例如1-α-氟-25-羟基-16,23-二烯-26,27-双同型-20-表-胆钙化醇，用于预防或治疗膀胱功能障碍。