(3aR,4S,7aR)-5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl]-cyclopropyl}-2-methyl-pent-3-yn-2-ol | 848945-74-4

• 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: (3aR,4S,7aR)-5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl]-cyclopropyl}-2-methyl-pent-3-yn-2-ol
• 英文别名: (3aR,4S,7aS)-5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl]-cyclopropyl}-2-methyl-pent-3-yn-2-ol；(3aR,4S,7aR)-5-[1-[4-(tert-butyldimethylsilanyloxy)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl]-cyclopropyl]-2-methylpent-3-yn-2-ol；5-[1-[(3aR,4S,7aS)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-3,3a,4,5,6,7-hexahydroinden-1-yl]cyclopropyl]-2-methylpent-3-yn-2-ol
• CAS: 848945-74-4
• 化学式: C₂₅H₄₂O₂Si
• 分子量: 402.693
• InChiKey: TWOREVSPNUYVCD-SKPFHBQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.46
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aR,4S,7aR)-5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl]-cyclopropyl}-2-methyl-pent-3-yn-2-ol 在 5% Pd-CaCO3 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 喹啉 、 乙醇 、 正己烷 、 乙酸乙酯 为溶剂， 反应 50.0h， 生成 (3aR,4S,7aR)-7a-methyl-1-[1-(4-hydroxy-4-methyl-pent-2Z-enyl)-cyclopropyl]-3a,4,5,6,7,7a-hexahydro-3H-inden-4-ol
  参考文献：
  名称：

  WO2006/100285

  摘要：

  公开号：
• 作为产物：
  描述：

  丙酮 在 正丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.75h， 生成 (3aR,4S,7aR)-5-{1-[4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-3a,4,5,6,7,7a-hexahydro-3H-inden-1-yl]-cyclopropyl}-2-methyl-pent-3-yn-2-ol
  参考文献：
  名称：

  [EN] 20-CYCLOALKYL,26,27-ALKYL/HALOALKYL VITAMIN D3 COMPOUNDS AND METHODS OF USE THEREOF
  [FR] COMPOSES DE VITAMINE D3 SOUS FORME DE 20-CYCLOALKYL,26,27-ALKYL/HALOALKYLE ET LEURS PROCEDES D'UTILISATION

  摘要：

  公开号：

  WO2006036813A3

文献信息

• [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。
• WO2006/51106
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Anti-inflammatory Properties of 1α,25-Dihydroxy-16-ene-20-cyclopropyl-24-<i>oxo</i>-vitamin D₃, a Hypocalcemic, Stable Metabolite of 1α,25-Dihydroxy-16-ene-20-cyclopropyl-vitamin D₃
  作者：Gilles Laverny、Giuseppe Penna、Milan Uskokovic、Stanislaw Marczak、Hubert Maehr、Pawel Jankowski、Caroline Ceailles、Paul Vouros、Brenden Smith、Matthew Robinson、G. Satyanarayana Reddy、Luciano Adorini

  DOI：10.1021/jm801365a

  日期：2009.4.23

  1 alpha,25(OH)(2)-16-ene-20-cyclopropyl-vitamin D-3 (13) is several fold more potent than the natural hormone 1 alpha,25-dihydroxyvitamin D-3 (1) as an anti-infilammatory agent. Here, we have further analyzed the anti-inflammatory properties of 13, confirming it as the most potent analogue tested within this family. We then determined the structures of all the natural metabolites of 13, including the 24-oxo metabolite 14, and carried out its synthesis. A comparison of 13 with 14 showed a similar induction of the primary VDR target genes CYP24A1 and CAMP and comparable anti-inflammatory properties as revealed by a similar inhibition of TNF-alpha, IL-12/23p40, IL-6, and IFN-gamma production. Interestingly, 14 displays a 3-fold lower calcemic activity in vivo compared to 13. Collectively, these findings indicate that the strong potency of 13 can be explained by the accumulation of its stable 24-oxo metabolite, which shows immunoregulatory and anti-inflammatory properties superimposable, to those exerted by 13 itself.