1-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1-propanone | 25017-89-4

• 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: 1-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1-propanone
• 英文别名: 2-(4-hydroxyphenyl)-1-(4-methoxyphenyl)propan-1-one；1-<4-Methoxy-phenyl>-2-<4-hydroxy-phenyl>-propanon-1；1-Propanone, 2-(4-hydroxyphenyl)-1-(4-methoxyphenyl)-
• CAS: 25017-89-4
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: RQEKWXGYMFYNHH-UHFFFAOYSA-N

物化性质

• 沸点：
  434.0±25.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1-propanone 在 盐酸 、 正丁基锂 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 环己烷 为溶剂， 反应 3.08h， 生成 1-(4-methoxyphenyl)-2-{4-[2-(piperidin-1-yl)ethoxy]phenyl}-1-(6-methoxynaphthalen-2-yl)propene
  参考文献：
  名称：

  In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆

  摘要：

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.051
• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2-(4-aminophenyl)-1-propanone 在 盐酸 、 sodium nitrite 、 氟硼酸钠 、 potassium carbonate 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 26.5h， 以74.8%的产率得到1-(4-methoxyphenyl)-2-(4-hydroxyphenyl)-1-propanone
  参考文献：
  名称：

  从头开始设计，合成和评估雌激素受体的非甾体二苯基萘基丙烯配体。

  摘要：

  仍然强烈需要额外的多样性和新的化学支架，以探索改善的组织选择性并寻找更好的选择性雌激素受体调节剂（SERM）。使用从头设计技术，已产生具有ER拮抗剂活性的二苯基萘丙烯支架，以（E）-9b为例。通过在金属卤素交换条件下用1-碘-6-甲氧基-萘对1- [4-甲氧基苯基）-2-（4-（2-氯乙氧基）苯基] -1-丙酮进行烷基化制备。 （E）-9b是通过吡咯烷置换氯而形成的（E）-9b与ER结合产生的h（α）的计算K（i）值对于hERα为3.7 nM，对于hERβ为72 nM ）。（E）-9b的拮抗作用在使用vitA2启动子和天然ER响应性pS2启动子的ERE的细胞转染测定中得到证实。随着（E）-9b浓度的增加，E（2）依赖的反应被有效抑制，表明（E）-9b可以在这些测定中起抗雌激素的作用。有趣的是，甚至低于基础水平也抑制了ERα的活性，这表明ERα的非配体依赖性活性也被抑制了。计算对接研究表明，

  DOI：

  10.1016/s0968-0896(02)00647-8

文献信息

• 1,2-diphenyl-1-naphthyl ethene derivatives, analogs and use thereof
  申请人：——

  公开号：US20020147187A1

  公开（公告）日：2002-10-10

  Molecules demonstrating anti-proliferative effects against epithelial cancer cell lines, human estrogen-dependent cancer cells and endothelial cells are disclosed. The molecules are intended for use in therapeutic preparations for the treatment of various cancers. The compounds specified are 1,2-diphenyl-1-naphthyl ethene derivatives.

  本发明公开了一种对上皮癌细胞系、人类雌激素依赖性癌细胞和内皮细胞具有抗增殖效应的分子。这些分子旨在用于治疗各种癌症的治疗制剂中。具体化合物为1,2-二苯基-1-萘乙烯衍生物。
• [EN] 1,2-DIPHENYL-1-NAPHTHYL ETHENE DERIVATIVES, ANALOGS AND USE THEREOF<br/>[FR] DERIVES 1,2-DIPHENYL-1-NAPHTYL ETHENE, ANALOGUES ET UTILISATION DE CES DERNIERS
  申请人：NANODESIGN INC

  公开号：WO2002066451A2

  公开（公告）日：2002-08-29

  Molecules of Formula (I), epithelial cancer cell lines, human estrogen-dependent cancer cells and endothelial cells are disclosed. The molecules are intended for use in therapeutic preparations for the treatment of various cancers. The compounds specified are 1,2-diphenyl-1-naphthyl ethene derivatives.
• In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor☆
  作者：Jonathan M. Schmidt、Gilles B. Tremblay、Michael A. Plastina、Fupeng Ma、Sanjivanjit Bhal (neé Basra)、Miklos Feher、Robert Dunn-Dufault、Peter R. Redden

  DOI：10.1016/j.bmc.2004.11.051

  日期：2005.3.1

  There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphenylnaphthyl propylene ligand 1. All compounds gave K(j)s under 10 nM when assayed in the presence of ERalpha. Generally these compounds had very high affinity for both ER isotypes. Moving the hydroxyl group on naphthalene from the 6- to the 5-position of the alpha-naphthalene attached compounds (6b and 6e vs 6c and 6f) had little affect on ER binding nor did altering the position of the naphthalene attachment (alpha or beta) to the alkene moiety. In transfection assays none of the compounds displayed agonistic activity in the absence of E-2. In MCF-7 proliferation assays 6a-d, 6f and 12a-c successfully abrogated E-2 stimulation and resulted in greater than 50% inhibition at 1 muM, a level of efficacy similar to that obtained when the cells were treated with raloxifene. Our results show that this new class of SERMs are good candidates for further study as therapeutic agents for the treatment of breast cancer and osteoporosis. (C) 2004 Elsevier Ltd. All rights reserved.
• De novo design, synthesis and evaluation of a non-steroidal diphenylnaphthyl propylene ligand for the estrogen receptor
  作者：Jonathan M Schmidt、Julie Mercure、Gilles B Tremblay、Martine Pagé、Miklos Feher、Robert Dunn-Dufault、Markus G Peter、Peter R Redden

  DOI：10.1016/s0968-0896(02)00647-8

  日期：2003.4

  strong need for additional diversity and new chemical scaffolds to allow for the exploration of improved tissue selectivity and finding better selective estrogen receptor modulators (SERMs). Using a de novo design technology a diphenylnaphthyl propylene scaffold, exemplified by (E)-9b, with ER antagonist activity has been generated. It was prepared by alkylating 1-[4-methoxyphenyl)-2-(4-(2-chloroethoxy)phenyl]-1-propanone

  仍然强烈需要额外的多样性和新的化学支架，以探索改善的组织选择性并寻找更好的选择性雌激素受体调节剂（SERM）。使用从头设计技术，已产生具有ER拮抗剂活性的二苯基萘丙烯支架，以（E）-9b为例。通过在金属卤素交换条件下用1-碘-6-甲氧基-萘对1- [4-甲氧基苯基）-2-（4-（2-氯乙氧基）苯基] -1-丙酮进行烷基化制备。 （E）-9b是通过吡咯烷置换氯而形成的（E）-9b与ER结合产生的h（α）的计算K（i）值对于hERα为3.7 nM，对于hERβ为72 nM ）。（E）-9b的拮抗作用在使用vitA2启动子和天然ER响应性pS2启动子的ERE的细胞转染测定中得到证实。随着（E）-9b浓度的增加，E（2）依赖的反应被有效抑制，表明（E）-9b可以在这些测定中起抗雌激素的作用。有趣的是，甚至低于基础水平也抑制了ERα的活性，这表明ERα的非配体依赖性活性也被抑制了。计算对接研究表明，