4-[8-(tert-butyldimethylsilyloxy)oct-1-ynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-ol | 252947-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫铬烷
• 英文名称: 4-[8-(tert-butyldimethylsilyloxy)oct-1-ynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-ol
• 英文别名: 4-[8-(t-Butyldimethylsilyloxy)-1-octynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman；4-[8-(t-Butyldimethylsilyloxy)-1-octynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromane；4-[8-[tert-butyl(dimethyl)silyl]oxyoct-1-ynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methyl-2H-thiochromen-4-ol
• CAS: 252947-38-9
• 化学式: C₃₂H₄₆O₄SSi
• 分子量: 554.866
• InChiKey: JHALPVQSMXWTJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.93
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  73.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[8-(tert-butyldimethylsilyloxy)oct-1-ynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-ol 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 8-[7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-yl]octan-1-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
• 作为产物：
  描述：

  (6-溴己氧基)-叔丁基二甲基硅烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 生成 4-[8-(tert-butyldimethylsilyloxy)oct-1-ynyl]-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-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

文献信息

• Benzopyran or thiobenzopyran derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US06645951B1

  公开（公告）日：2003-11-11

  The present invention provides novel benzopyran compounds, pharmaceutically acceptable salts thereof and stereoisomers thereof where the benzopyran compounds of the invention are compounds according to Formula I: The present invention further provides pharmaceutical compositions which possess anti-estrogenic activity and comprise at least one benzopyran compound of the invention and a method of treating breast cancer by administration of an effective amount of a benzopyran compound provided by the present invention.

  本发明提供了新颖的苯并吡喃化合物，其药学上可接受的盐及其立体异构体，其中本发明的苯并吡喃化合物是根据式I的化合物：本发明还提供了具有抗雌激素活性的药物组合物，包括本发明的至少一种苯并吡喃化合物，并通过给予本发明提供的苯并吡喃化合物的有效量来治疗乳腺癌的方法。
• Metal salts of 3-methyl-chromane or thiochromane derivatives
  申请人：——

  公开号：US20030092695A1

  公开（公告）日：2003-05-15

  The present invention relates to metal salts of 3-methyl-chromane or thiochromane derivatives, stereoisomers or hydrates thereof, and an anti-estrogenic pharmaceutical composition which comprises the above compound as an active component and exhibits a highly improved solubility.

  本发明涉及3-甲基-色酮或硫代色酮衍生物的金属盐、立体异构体或水合物，以及一种抗雌激素药物组合物，其包括上述化合物作为活性成分，并具有高度改善的溶解度。
• Discovery of thiochroman and chroman derivatives as pure antiestrogens and their structure–activity relationship
  作者：Yoshitake Kanbe、Myung-Hwa Kim、Masahiro Nishimoto、Yoshihito Ohtake、Nobuaki Kato、Toshiaki Tsunenari、Kenji Taniguchi、Iwao Ohizumi、Shin-ichi Kaiho、Kazumi Morikawa

  DOI：10.1016/j.bmc.2006.03.020

  日期：2006.7.15

  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.