1α,25-dihydroxyvitamin D₃-3β-bromoacetate

• 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: 1α,25-dihydroxyvitamin D₃-3β-bromoacetate
• 英文别名: 1α,25-dihydroxy-5Z-vitamin D3-3β-bromoacetate；1α,25-dihydroxyvitamin D3-3β-(2-bromoacetate)；1,25(OH)2D3-3-BE；AMPI-109；1α,25-dihydroxy-vitamin D3-3β-(2)-bromoacetate；[(1R,3Z,5S)-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-hydroxy-4-methylidenecyclohexyl] 2-bromoacetate
• 化学式: C₂₉H₄₅BrO₄
• 分子量: 537.578
• InChiKey: SLFLGLKEAANGNN-RBDVLXGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  25-hydroxy-5E-[6,19,19'-H3]vitamin D3-3β-tert-butyldimethylsilyl ether 在 4-二甲氨基吡啶 、 selenium(IV) oxide 、 蒽 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 2.75h， 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

文献信息

• 1α,25-Dihydroxyvitamin D3-3β-bromoacetate, an Affinity-Labeling Analog of 1α,25-Dihydroxyvitamin D3 Receptor
  作者：R. Ray、S. Ray、M.F. Holick

  DOI：10.1006/bioo.1994.1021

  日期：1994.9

  In this communication we describe the synthesis of 1 alpha,25-dihydroxyvitamin D-3-3 beta-bromoacetate [1,25(OH)(2)-BE], an analog of 1 alpha,25-dihydroxyvitamin D-3 [1,25(OH)(2)D-3], as a part of our ongoing interest in characterizing the hormone-binding domain of the 1 alpha,25-dihydroxyvitamin D-3 receptor (VDR). We carried out several binding studies of 1,25(OH)(2)-BE with chick intestinal VDR preparations to demonstrate that 1,25(OH)(2)-BE is capable of blocking the entry of 1,25(OH)(2)D-3 into its binding pocket and possibly covalently linking to the VDR molcule. (C) 1994 Academic Press, Inc.