4-{1-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenol | 865239-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{1-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenol
• 英文别名: 4-{1-[4-((R)-2,2-Dimethyl-[1,3]dioxolan4-ylmethoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenol；4-[3-[4-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-3-methylphenyl]pentan-3-yl]-2-methylphenol
• CAS: 865239-03-8
• 化学式: C₂₅H₃₄O₄
• 分子量: 398.543
• InChiKey: IHOHSCRQKIIAOU-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-{1-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenol 、 1-金刚烷基溴甲酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-1-(adamantan-1-yl)-2-(4-(3-(4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3-methylphenyl)pentan-3-yl)-2-methylphenoxy)ethan-1-one
  参考文献：
  名称：

  Novel selective anti-androgens with a diphenylpentane skeleton

  摘要：

  We have proposed a multi-template approach for drug development, focusing on similar fold structures of proteins, and have effectively generated lead compounds for several drug targets. Modification of these polypharmacological lead compounds is then needed to generate target-selective compounds. In the work presented here, we aimed at separation of the anti-androgen activity and vitamin D activity of previously identified diphenylpentane lead compounds. Based on the determined X-ray crystal structures of androgen receptor and vitamin D receptor, bulky substituents were introduced at the t-butyl group in the lead compounds 2 and 3. As a result of this structural development, we obtained 16c, which exhibits more potent anti-androgen activity (IC(50): 0.13 mu M) than clinically used anti-androgen bicalutamide (IC(50): 0.67 mu M) with 30-fold selectivity over vitamin D activity. This result indicates that lead compounds obtained via the multi-template approach can indeed be structurally modified to generate target-selective compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.011
• 作为产物：
  描述：

  3,3-bis[4-hydroxy-3-methylphenyl]pentane 、 对甲苯磺酸(S)-(-)-2,2-二甲基-1,3-二氧戊环基-4-基甲基酯 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 12.08h， 以42.6%的产率得到4-{1-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenol
  参考文献：
  名称：

  [EN] BISPHENYL COMPOUNDS USEFUL AS VITAMIN D3 RECEPTOR AGONISTS
  [FR] COMPOSES DE BISPHENYLE UTILES EN TANT QU'AGONISTES DE RECEPTEURS DE LA VITAMINE D3

  摘要：

  公开号：

  WO2005087700A3

文献信息

• Bisphenyl compounds useful as vitamin D3 receptor agonists
  申请人：Wallace David

  公开号：US20060025474A1

  公开（公告）日：2006-02-02

  The present invention discloses bisphenyl compounds of the formula: wherein R1, R2, R3, R4, R5, R6, X, Y, W are defined herein after. These compounds are useful as pharmaceuticals.

  本发明公开了以下式子的双苯基化合物：其中R1，R2，R3，R4，R5，R6，X，Y，W的定义见下文。这些化合物可用作药物。
• BISPHENYL COMPOUNDS USEFUL AS VITAMIN D SB 3 /SB RECEPTOR AGONISTS
  申请人：CHUGAI SEIYAKU KABUSHIKI KAISHA

  公开号：EP1740522A2

  公开（公告）日：2007-01-10