E-hydroxymethyl-N,N-diethyltamoxifen | 133157-93-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: E-hydroxymethyl-N,N-diethyltamoxifen
• 英文别名: (E)-1-<4-(2-diethylaminoethoxy)phenyl>-1,2-diphenyl-1-penten-5-ol；(E)-5-[4-[2-(diethylamino)ethoxy]phenyl]-4,5-diphenylpent-4-en-1-ol
• CAS: 133157-93-4
• 化学式: C₂₉H₃₅NO₂
• 分子量: 429.602
• InChiKey: PJBBXBRTNRRJDO-ZQHSETAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三甲氧基酯 、 恩氯米芬 在 叔丁基锂 作用下， 生成 trans-hydroxymethyl-N,N-diethyltamoxifen 、 E-hydroxymethyl-N,N-diethyltamoxifen
  参考文献：
  名称：

  N,N-Diethylfluoromethyltamoxifen: Synthesis, assignment of 1H and 13C spectra and receptor assay

  摘要：

  (cis) and (trans)N,N-diethylfluoromethyltamoxifen (1-14-(2-diethylaminoethoxy)phenyl]-1,2-diphenyl-5-fluoro-1-pentene) were synthesized from clomiphene in a three-step procedure and both isomers were differentiated by the concerted application of two-dimensional NMR techniques. In in vitro estrogen receptor assay from pig uterus using [H-3]-estradiol (5 nM), the IC50 values were: NN-diethylfluorotamoxifen cis 5 muM, trans 1 muM; tamoxifen 30 muM. In human MCF7 cell growth assay, the IC50 values were cis 4.5 muM, trans 11.8 muM, tamoxifen 11.0 muM. The data suggest that the fluoro analog of tamoxifen has potential for imaging estrogen receptors by positron emission tomography (PET) and may be used to predict the efficacy of breast tumor therapy.

  DOI：

  10.1016/0223-5234(92)90023-t

文献信息

• N,N-Diethylfluoromethyltamoxifen: Synthesis, assignment of 1H and 13C spectra and receptor assay
  作者：DJ Yang、A Cherif、W Tansey、LR Kuang、C Li、KC Wright、EE Kim、S Wallace

  DOI：10.1016/0223-5234(92)90023-t

  日期：1992.12

  (cis) and (trans)N,N-diethylfluoromethyltamoxifen (1-14-(2-diethylaminoethoxy)phenyl]-1,2-diphenyl-5-fluoro-1-pentene) were synthesized from clomiphene in a three-step procedure and both isomers were differentiated by the concerted application of two-dimensional NMR techniques. In in vitro estrogen receptor assay from pig uterus using [H-3]-estradiol (5 nM), the IC50 values were: NN-diethylfluorotamoxifen cis 5 muM, trans 1 muM; tamoxifen 30 muM. In human MCF7 cell growth assay, the IC50 values were cis 4.5 muM, trans 11.8 muM, tamoxifen 11.0 muM. The data suggest that the fluoro analog of tamoxifen has potential for imaging estrogen receptors by positron emission tomography (PET) and may be used to predict the efficacy of breast tumor therapy.