4-[10-(tert-butyldimethylsilyloxy)dec-1-ynyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman-4-ol | 902799-60-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[10-(tert-butyldimethylsilyloxy)dec-1-ynyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman-4-ol
• CAS: 902799-60-4
• 化学式: C₃₆H₅₄O₇Si
• 分子量: 626.906
• InChiKey: TXYDMWSLOVBJTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-[10-(tert-butyldimethylsilyloxy)dec-1-ynyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman-4-ol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 4-[10-(tert-butyldimethylsilyloxy)decyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylchroman 、 4-[10-(tert-butyldimethylsilyloxy)decyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylchroman
  参考文献：
  名称：

  Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure–activity relationship

  摘要：

  In order to develop pure antiestrogens, a series of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman and 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman derivatives with sulfoxide containing side chains at the 4-position were designed, synthesized, and evaluated. Among them, compounds 14b and 24b functioned as pure antiestrogens with the ability to downregulate ER, and their in vitro and in vivo antiestrogen activities were similar to those of ICI182,780. In addition, the structure-activity relationship indicated that the (3RS,4RS)-configuration between the 3- and 4-position, the methyl group at the 3-position, the 9-methylene chain between the scaffold and the sulfoxide moiety, and the terminal perfluoroalkyl moiety play an important role in increasing estrogen receptor binding and oral antiestrogen activities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.020
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 乙腈 为溶剂， 生成 4-[10-(tert-butyldimethylsilyloxy)dec-1-ynyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman-4-ol
  参考文献：
  名称：

  Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure–activity relationship

  摘要：

  In order to develop pure antiestrogens, a series of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylchroman and 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman derivatives with sulfoxide containing side chains at the 4-position were designed, synthesized, and evaluated. Among them, compounds 14b and 24b functioned as pure antiestrogens with the ability to downregulate ER, and their in vitro and in vivo antiestrogen activities were similar to those of ICI182,780. In addition, the structure-activity relationship indicated that the (3RS,4RS)-configuration between the 3- and 4-position, the methyl group at the 3-position, the 9-methylene chain between the scaffold and the sulfoxide moiety, and the terminal perfluoroalkyl moiety play an important role in increasing estrogen receptor binding and oral antiestrogen activities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.020