4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman

• 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-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman
• 英文别名: tert-butyl-[9-[7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methyl-2,4-dihydrothiochromen-4-yl]non-8-ynoxy]-dimethylsilane
• 化学式: C₃₅H₅₂O₅SSi
• 分子量: 612.946
• InChiKey: HFFXSCYPCROJQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.17
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium azide 、 四丁基氟化铵 、 氢气 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-[9-[(3S,4S)-7-hydroxy-3-(4-hydroxyphenyl)-3-methyl-2,4-dihydrothiochromen-4-yl]nonyl]-3-(4,4,5,5,5-pentafluoropentylsulfonyl)urea
  参考文献：
  名称：

  Discovery of thiochroman derivatives bearing a carboxy-containing side chain as orally active pure antiestrogens

  摘要：

  In order to search for alternatives to the sulfoxide moiety in the long side chain of pure antiestrogens, several molecules that may interact with water in a fashion similar to ICI164,384 were designed and it was found that compounds with the carboxy, the sulfamide, or the sulfonamide instead of the sulfoxide moiety also functioned as pure antiestrogens. Interestingly, the compound possessing the carboxy moiety showed superior antiestrogen activity compared to ICI182,780 when dosed orally. Results of the pharmacokinctic evaluation indicated that the potent antiestrogen activity at oral dosing attributed to both the improved absorption from the intestinal wall and the metabolic stability of the compound in liver. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.090
• 作为产物：
  描述：

  7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylthiochroman-4-one 、 9-(tert-butyldimethylsilyloxy)non-1-yne 在 正丁基锂 、 sodium cyanoborohydride 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 4-[9-(t-butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman
  参考文献：
  名称：

  Discovery of thiochroman derivatives bearing a carboxy-containing side chain as orally active pure antiestrogens

  摘要：

  In order to search for alternatives to the sulfoxide moiety in the long side chain of pure antiestrogens, several molecules that may interact with water in a fashion similar to ICI164,384 were designed and it was found that compounds with the carboxy, the sulfamide, or the sulfonamide instead of the sulfoxide moiety also functioned as pure antiestrogens. Interestingly, the compound possessing the carboxy moiety showed superior antiestrogen activity compared to ICI182,780 when dosed orally. Results of the pharmacokinctic evaluation indicated that the potent antiestrogen activity at oral dosing attributed to both the improved absorption from the intestinal wall and the metabolic stability of the compound in liver. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.090

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。
• Discovery of thiochroman derivatives bearing a carboxy-containing side chain as orally active pure antiestrogens
  作者：Yoshitake Kanbe、Myung-Hwa Kim、Masahiro Nishimoto、Yoshihito Ohtake、Toshiaki Tsunenari、Kenji Taniguchi、Iwao Ohizumi、Shin-ichi Kaiho、Yoshiaki Nabuchi、Setsu Kawata、Kazumi Morikawa、Jae-Chon Jo、Hee-An Kwon、Hyun-Suk Lim、Hak-Yeop Kim

  DOI：10.1016/j.bmcl.2006.04.090

  日期：2006.8

  In order to search for alternatives to the sulfoxide moiety in the long side chain of pure antiestrogens, several molecules that may interact with water in a fashion similar to ICI164,384 were designed and it was found that compounds with the carboxy, the sulfamide, or the sulfonamide instead of the sulfoxide moiety also functioned as pure antiestrogens. Interestingly, the compound possessing the carboxy moiety showed superior antiestrogen activity compared to ICI182,780 when dosed orally. Results of the pharmacokinctic evaluation indicated that the potent antiestrogen activity at oral dosing attributed to both the improved absorption from the intestinal wall and the metabolic stability of the compound in liver. (c) 2006 Elsevier Ltd. All rights reserved.