(1S,5R,Z)-5-((叔丁基二甲基硅烷基)氧基)-3-((E)-2-((1R,3AS,7AR)-1-((R)-6-羟基-6-甲基庚烷-2-基)-7A-甲基六氢-1H-茚-4(2H)-亚基)亚乙基)-2-甲基环己醇 | 132054-64-9

• 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
• 中文名称: (1S,5R,Z)-5-((叔丁基二甲基硅烷基)氧基)-3-((E)-2-((1R,3AS,7AR)-1-((R)-6-羟基-6-甲基庚烷-2-基)-7A-甲基六氢-1H-茚-4(2H)-亚基)亚乙基)-2-甲基环己醇
• 中文别名: (1S,5R,Z)-5-((叔丁基二甲基硅烷基)氧基)-3-((E)-2-((1R,3A
• 英文名称: 1α-[((trimethylsilyl)-oxy)]-3β-[((tertiary-butyl-dimethylsilyl)-oxy)], 25-trihydroxy-9,10-5(Z),7(E),10(19)-triene
• 英文别名: 1α,25-dihydroxy-5Z-vitamin D3-3β-tert-butyldimethylsilyl ether；1α,25-dihydroxyvitamin D3-3β-tert-butyldimethylsilyl ether；1α,25-dihydroxyvitamin D3-3-TBDMS ether；(1S,5R,Z)-5-(tert-butyldimethylsilyloxy)-3-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)-2-Methylenecyclohexanol；(1S,3Z,5R)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylidenecyclohexan-1-ol
• CAS: 132054-64-9
• 化学式: C₃₃H₅₈O₃Si
• 分子量: 530.907
• InChiKey: LBFNORYGGFZIBM-VPPRDYJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.73
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,5R,Z)-5-((叔丁基二甲基硅烷基)氧基)-3-((E)-2-((1R,3AS,7AR)-1-((R)-6-羟基-6-甲基庚烷-2-基)-7A-甲基六氢-1H-茚-4(2H)-亚基)亚乙基)-2-甲基环己醇 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 1α,25-dihydroxyvitamin D₃-3β-bromoacetate
  参考文献：
  名称：

  1α,25-Dihydroxyvitamin D3-3β-bromoacetate, a potential cancer therapeutic agent: Synthesis and molecular mechanism of action

  摘要：

  Synthesis of 1 alpha,25-dihydroxyvitamin D-3-3 beta-bromoacetate (1,25(OH)(2)D-3-3-BE), a potential anti-cancer agent is presented. We also report that mechanism of action of 1,25(OH)(2)D-3-3-BE may involve reduction of its catabolism, as evidenced by the reduced and delayed expression of 1 alpha,25-dihydroxyvitamin D-3-24-hydroxylase (CYP24) gene in cellular assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.025
• 作为产物：
  描述：

  25-hydroxy-5E-[6,19,19'-H3]vitamin D3-3β-tert-butyldimethylsilyl ether 在 selenium(IV) oxide 、 蒽 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.75h， 生成 (1S,5R,Z)-5-((叔丁基二甲基硅烷基)氧基)-3-((E)-2-((1R,3AS,7AR)-1-((R)-6-羟基-6-甲基庚烷-2-基)-7A-甲基六氢-1H-茚-4(2H)-亚基)亚乙基)-2-甲基环己醇
  参考文献：
  名称：

  1α,25-Dihydroxyvitamin D3-3β-bromoacetate, a potential cancer therapeutic agent: Synthesis and molecular mechanism of action

  摘要：

  Synthesis of 1 alpha,25-dihydroxyvitamin D-3-3 beta-bromoacetate (1,25(OH)(2)D-3-3-BE), a potential anti-cancer agent is presented. We also report that mechanism of action of 1,25(OH)(2)D-3-3-BE may involve reduction of its catabolism, as evidenced by the reduced and delayed expression of 1 alpha,25-dihydroxyvitamin D-3-24-hydroxylase (CYP24) gene in cellular assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.025

文献信息

• Rational Design of Vitamin D₃ Analogues Which Selectively Restore Activity to a Vitamin D Receptor Mutant Associated with Rickets
  作者：Steve L. Swann、Joel J. Bergh、M. Cindy Farach-Carson、John T. Koh

  DOI：10.1021/ol0266931

  日期：2002.10.1

  graphicVitamin D-3-resistant rickets (VDRR) is associated with mutations to the Vitamin D receptor (VDR) which effect ligand-dependent transactivation. Some VDRR associated mutants directly disrupt ligand binding. Using the reported VDR-1,25-dihydroxy vitamin D-3 (1,25(OH)(2)D-3) cocrystal structure, three 1,25(OH)2D3 analogues were designed to uniquely complement the rickets associated mutant VDR(Arg274-->Leu). The three analogues were 17 to 286 times more potent than 1,25(OH)(2)D-3 with the mutant in cell-based assays and did not substantially activate cellular calcium influx.
• Photoaffinity labeling of chick intestinal 1α,25-dihydroxyvitamin D3 receptor
  作者：Rahul Ray、Swapna Ray、Stanley Rose、Michael F. Holick

  DOI：10.1016/0039-128x(93)90003-6

  日期：1993.10

  The photoaffinity labeling of chick intestinal 1alpha,25-dihydroxyvitamin D3 receptor with 1alpha,25-dihydroxyvitamin D3-3beta-N-(4-azido-2-nitro-[3,5-H-3]phenyl)}glycinate has been determined under a variety of conditions.