5R-3-{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}propan-1-ol | 554431-86-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5R-3-{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}propan-1-ol
• 英文别名: 3-[4-[(19R)-5,15-bis[[tert-butyl(dimethyl)silyl]oxy]-8,18-dioxatetracyclo[9.8.0.02,7.012,17]nonadeca-1(11),2(7),3,5,12(17),13,15-heptaen-19-yl]phenoxy]propan-1-ol
• CAS: 554431-86-6
• 化学式: C₃₈H₅₂O₆Si₂
• 分子量: 660.998
• InChiKey: GIMRNACERAOKFJ-PSXMRANNSA-N

物化性质

• 沸点：
  664.7±55.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.04
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5R-3-{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}propan-1-ol 在 甲基三苯氧基碘磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (S)-2,8-bis-(tert-butyldimethylsilanyloxy)-5-[4-(3-iodo-propoxy)-phenyl]-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalene
  参考文献：
  名称：

  Identification and Structure−Activity Relationships of Chromene-Derived Selective Estrogen Receptor Modulators for Treatment of Postmenopausal Symptoms

  摘要：

  As part of it program aimed at the development of selective estrogen receptor modulators (SERMs), novel chromene scaffolds, benzopyranobenzoxapanes, were discovered. Many compounds showed binding affinity as low as 1.6-200 nM, displayed antagonist behaviors in the MCF-7 human breast adenocarcinoma cell line its well in Ishikawa cell line with IC50 values in the range 0.2-360 nM. On the basis of the side chain substitution, various compounds demonstrated strong inhibitory activity in anti-uterotropic assay. Compound 7-(R) and its major metabolites 5-(R) and 6-(R) were evaluated in several in vivo models of estrogen action. Relative to a full estrogen agonist (ethynyl estradiol) and file SERM raloxifene, 7-(R) wits found to be it potent SERM that behaved its antagonist in the uterus and exhibited estrogen agonistic activity on bone, plasma lipids, hot flush, and vagina. The overall pharmacokinetic profile and stability were Significantly improved compared to those of the phase 2 development compound 9-(R).

  DOI：

  10.1021/jm900146e
• 作为产物：
  描述：

  3-{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}propan-1-ol 生成 5S-3-{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}propan-1-ol 、 5R-3-{4-[2,8-bis-(tert-butyldimethylsilanyloxy)-11,12-dihydro-5H-6,13-dioxabenzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]phenoxy}propan-1-ol
  参考文献：
  名称：

  Identification and Structure−Activity Relationships of Chromene-Derived Selective Estrogen Receptor Modulators for Treatment of Postmenopausal Symptoms

  摘要：

  As part of it program aimed at the development of selective estrogen receptor modulators (SERMs), novel chromene scaffolds, benzopyranobenzoxapanes, were discovered. Many compounds showed binding affinity as low as 1.6-200 nM, displayed antagonist behaviors in the MCF-7 human breast adenocarcinoma cell line its well in Ishikawa cell line with IC50 values in the range 0.2-360 nM. On the basis of the side chain substitution, various compounds demonstrated strong inhibitory activity in anti-uterotropic assay. Compound 7-(R) and its major metabolites 5-(R) and 6-(R) were evaluated in several in vivo models of estrogen action. Relative to a full estrogen agonist (ethynyl estradiol) and file SERM raloxifene, 7-(R) wits found to be it potent SERM that behaved its antagonist in the uterus and exhibited estrogen agonistic activity on bone, plasma lipids, hot flush, and vagina. The overall pharmacokinetic profile and stability were Significantly improved compared to those of the phase 2 development compound 9-(R).

  DOI：

  10.1021/jm900146e