2-[3-(tert-butyldimethylsilyloxymethyl)-2,5-bis(methoxymethoxy)-3-methoxymethylphenyl]cyclopent-1-enecarboxylic acid methyl ester | 787615-76-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 2-[3-(tert-butyldimethylsilyloxymethyl)-2,5-bis(methoxymethoxy)-3-methoxymethylphenyl]cyclopent-1-enecarboxylic acid methyl ester
• 英文别名: Methyl 2-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,5-bis(methoxymethoxy)phenyl]cyclopentene-1-carboxylate
• CAS: 787615-76-3
• 化学式: C₂₄H₃₈O₇Si
• 分子量: 466.647
• InChiKey: WPWCWXZOKLKGEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[3-(tert-butyldimethylsilyloxymethyl)-2,5-bis(methoxymethoxy)-3-methoxymethylphenyl]cyclopent-1-enecarboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 methyl (1S,2R)-2-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,5-bis(methoxymethoxy)phenyl]cyclopentane-1-carboxylate
  参考文献：
  名称：

  Benzopyrans as selective estrogen receptor β agonists (SERBAs). Part 4: Functionalization of the benzopyran A-ring

  摘要：

  Benzopyrans are selective estrogen receptor (ER) beta agonists (SERBAs), which bind the ER receptor subtypes alpha and beta in opposite orientations. We have used structure based drug design to show that this unique phenomena can be exploited via substitution at the 8-position of the benzopyran A-ring to disrupt binding to ER alpha, thus improving ER beta subtype selectivity. X-ray cocrystal structures with ER alpha and ER beta are supportive of this approach to improve selectivity in this structural class. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.009
• 作为产物：
  描述：

  [3-bromo-2,5-bis(methoxymethoxy)benzyloxy]-tert-butyldimethylsilane 、 methyl 2-(trifluoromethylsulfonyloxy)cyclopent-1-enecarboxylate 在 四(三苯基膦)钯 苯基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 生成 2-[3-(tert-butyldimethylsilyloxymethyl)-2,5-bis(methoxymethoxy)-3-methoxymethylphenyl]cyclopent-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Benzopyrans as selective estrogen receptor β agonists (SERBAs). Part 4: Functionalization of the benzopyran A-ring

  摘要：

  Benzopyrans are selective estrogen receptor (ER) beta agonists (SERBAs), which bind the ER receptor subtypes alpha and beta in opposite orientations. We have used structure based drug design to show that this unique phenomena can be exploited via substitution at the 8-position of the benzopyran A-ring to disrupt binding to ER alpha, thus improving ER beta subtype selectivity. X-ray cocrystal structures with ER alpha and ER beta are supportive of this approach to improve selectivity in this structural class. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.009

文献信息

• [EN] SUBSTITUTED BENZOPYRANS AS SELECTIVE ESTROGEN RECEPTOR-BETA AGONISTS<br/>[FR] BENZOPYRANES SUBSTITUES UTILES EN TANT QU'AGONISTES SELECTIFS DU RECEPTEUR BETA DES OESTROGENES
  申请人：LILLY CO ELI

  公开号：WO2004094401A1

  公开（公告）日：2004-11-04

  The present invention relates to substituted benzopyran derivatives, stereoisomers, and pharmaceutical acceptable salts thereof and processes for the preparation of the same. The compounds of the present invention are useful as Estrogen Receptor ? agonists. Such agonists are useful for the treating Estrogen Receptor ? mediated diseases such as prostate cancer or BPH.

  本发明涉及取代苯并吡喃衍生物、立体异构体及其药学上可接受的盐以及其制备方法。本发明的化合物可用作雌激素受体β激动剂。这种激动剂对于治疗雌激素受体β介导的疾病，如前列腺癌或BPH等是有用的。