4-[8-(tert-butyldimethylsilyloxy)oct-1-ynyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman-4-ol | 902799-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[8-(tert-butyldimethylsilyloxy)oct-1-ynyl]-7-methoxymethyloxy-3-(4-methoxymethyloxyphenyl)-3-methylchroman-4-ol
• 英文别名: (3RS,4RS)-4-[8-(t-butyldimethylsilyloxy)octynyl]-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran；4-[8-[tert-butyl(dimethyl)silyl]oxyoct-1-ynyl]-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-3-methyl-2H-chromen-4-ol
• CAS: 902799-45-5
• 化学式: C₃₄H₅₀O₇Si
• 分子量: 598.852
• InChiKey: YTXPAVQXTYIAOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.17
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[8-(tert-butyldimethylsilyloxy)oct-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， 反应 0.75h， 生成 4-[8-(tert-butyldimethylsilyloxy)octyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methylchroman 、 4-[8-(tert-butyldimethylsilyloxy)octyl]-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：

  (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-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

文献信息

• Benzopyran derivatives
  申请人：C & C Research Laboratories

  公开号：US06153768A1

  公开（公告）日：2000-11-28

  The present invention relates to a novel benzopyran derivative having anti-estrogenic activity. More specifically, the present invention relates to a novel benzopyran derivative represented by formula (I) and pharmaceutically acceptable salt thereof, in which ----- represents a single bond or a double bond; R1 and R2 independently of one another represent hydrogen, hydroxy or OR group, wherein R represents acyl or alkyl; R3 represents hydrogen, lower alkyl or halogeno lower alkyl, provided that when ----- represents a double bond, R3 is not present; R4 represents hydrogen or lower alkyl; A represents a group of formula a, b, c or d; R5, R6 and R7 independently of one another represent hydrogen, alkyl, halogenoalkyl, alkenyl or halogenoalkenyl, or R6 and R7 together with nitrogen atom to which they are bound can form a 4- to 8-membered heterocyclic ring which can be substituted with R5; X represents O, S, or NR8, wherein R8 represents hydrogen or lower alkyl; m denotes an integer of 2 to 15; n denotes an integer of 0 to 2; and p denotes an integer of 0 to 4.

  本发明涉及一种具有抗雌激素活性的新型苯并吡喃衍生物。更具体地，本发明涉及一种由式（I）表示的新型苯并吡喃衍生物及其药学上可接受的盐，其中-----表示单键或双键；R1和R2彼此独立地表示氢、羟基或OR基团，其中R表示酰基或烷基；R3表示氢、较低烷基或卤代较低烷基，但当-----表示双键时，R3不存在；R4表示氢或较低烷基；A表示a、b、c或d式的基团；R5、R6和R7彼此独立地表示氢、烷基、卤代烷基、烯基或卤代烯基，或者R6和R7与它们结合的氮原子一起可以形成一个4-至8-成员的杂环环，该环可以用R5取代；X表示O、S或NR8，其中R8表示氢或较低烷基；m表示2至15的整数；n表示0至2的整数；p表示0至4的整数。