(1R,3aR,7aR)-1-((S)-5-hydroxy-1-{2-[(R)-2-(4-methoxyphenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]ethyl}-5-methylhexyl)-7a-methyloctahydroinden-4-one | 770714-52-8

• 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: (1R,3aR,7aR)-1-((S)-5-hydroxy-1-{2-[(R)-2-(4-methoxyphenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]ethyl}-5-methylhexyl)-7a-methyloctahydroinden-4-one
• 英文别名: [1R,3aR,7aR]-1-(5-hydroxy-1(S)-{2-[2-(4-methoxy-phenyl)-5,5-dimethyl-[1,3]dioxolan-4(R)-yl]-ethyl}-5-methyl-hexyl)-7a-methyl-octahydro-inden-4-one；[1R,3aR,7aR]-1-(5-hydroxy-1(S)-[2-[2-(4-methoxyphenyl)-5,5-dimethyl-[1,3]dioxolan-4(R)-yl]-ethyl]-5-methyl-hexyl)-7a-methyl-octahydro-inden-4-one；[1R,3aR,7aR]-1-(5-hydroxy-1(S)-{2-[2-(4-methoxyphenyl)-5,5-dimethyl-[1,3]dioxolan-4(R)-yl]ethyl}-5-methylhexyl)-7a-methyloctahydroinden-4-one；(1R,3aR,7aR)-1-[(3S)-7-hydroxy-1-[(4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxolan-4-yl]-7-methyloctan-3-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 770714-52-8
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: DMEJDVBKWWHDFU-RZZYIFJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3aR,7aR)-1-((S)-5-hydroxy-1-{2-[(R)-2-(4-methoxyphenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]ethyl}-5-methylhexyl)-7a-methyloctahydroinden-4-one 在 咪唑 、 正丁基锂 、 N,N-dimethylpyridine 、 草酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.42h， 生成 [1R,3aR,7aR,4E]-4-{2(Z)-[3(S),5(R)-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-ethylidene}-7a-methyl-1-[5-methyl-1(S)-(4-methyl-4-triethylsilanyloxy-pentyl)-4(R),5-bis-triethylsilanyloxy-hexyl]-octahydro-indene
  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：

  (2R)-2,3-dihydroxy-3-methylbutan-1-yl p-toluenesulfonate 在 甲醇 、 sodium amalgam 、 重铬酸吡啶 、 正丁基锂 、 Celite 、 fluorosilic acid 、 4-甲基苯磺酸吡啶 、 草酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 40.67h， 生成 (1R,3aR,7aR)-1-((S)-5-hydroxy-1-{2-[(R)-2-(4-methoxyphenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]ethyl}-5-methylhexyl)-7a-methyloctahydroinden-4-one
  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

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。
• WO2006/51106
  申请人：——

  公开号：——

  公开（公告）日：——