1-(2-chloro-4-methoxyphenyl)-2-(4-methoxyphenyl)-ethane-1-one | 1001441-52-6

• 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-(2-chloro-4-methoxyphenyl)-2-(4-methoxyphenyl)-ethane-1-one
• 英文别名: 1-(2-chloro-4-methoxyphenyl)-2-(4-methoxyphenyl)ethan-1-one；1-(2-Chloro-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone
• CAS: 1001441-52-6
• 化学式: C₁₆H₁₅ClO₃
• 分子量: 290.746
• InChiKey: HFALOTAQQMQKDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-4-methoxyphenyl)-2-(4-methoxyphenyl)-ethane-1-one 在 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 2-(2-chloro-4-methoxyphenyl)-3,5-bis(4-methoxyphenyl)-1-methyl-1H-pyrrole
  参考文献：
  名称：

  Influence of Chlorine or Fluorine Substitution on the Estrogenic Properties of 1-Alkyl-2,3,5-tris(4-hydroxyphenyl)-1H-pyrroles

  摘要：

  In continuation of Our previous work, several 1- alkyl-2,3,5-tris(4-hydroxyphenyl)aryl-1H-pyrroles with chlor-Me or fluorine substituents in the aryl residues were synthesized and tested for estrogen receptor (ER) binding at isolated ER alpha/ER beta. receptors (HAP assay), and. in trans activation assays using ER alpha-positive MCF-7/2a as well as U2-OS/ER alpha and U2-OS/ER beta cells. In the competition experiment at ER alpha the compounds displayed very high relative binding-affinities of up to 37% (determined for 8m) but with restricted subtype selectivity (e.g., ER alpha/ER beta (8ma) = 9). The highest estrogenic potency in ER alpha-positive MCP-7/2a cells was determined for 2,3,5-tris(2-fluoro-4-hydroxyphenyl)-1-prolayl-1H-pyriole 8m (EC50 = 23 nM), while in U2-OS/ER alpha cells 2-(2-fluoro-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)-1H propyl-1H pyrrole 8b (EC50 = 0.12 nM) was the Most potent agonist, only 30 fold less active than estradiol (E2, EC50 = 0.004 nM). In U2-OS/ER beta cells for all pyrroles no transactivation could be observed, which indicates that they are selective ER alpha agonists in Cellular systems.

  DOI：

  10.1021/jm300860j
• 作为产物：
  描述：

  对甲氧基苯乙酸 、 3-氯苯甲醚 在 aluminum (III) chloride 氯化亚砜 、 盐酸 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.75h， 以28%的产率得到1-(2-chloro-4-methoxyphenyl)-2-(4-methoxyphenyl)-ethane-1-one
  参考文献：
  名称：

  WO2008/6626

  摘要：

  公开号：

文献信息

• Triphenyl modified 5-membered heterocycles and their use as anticancer and antiflammatory agents
  申请人：Freie Universität Berlin

  公开号：EP1889617A1

  公开（公告）日：2008-02-20

  The present invention provides 5-membered heterocycles, preferably pyrroles, furans and thiophenes, with three phenyl moieties wherein at least one of the three phenyl moieties is substituted with halogen or trihalomethyl. The compounds of the invention show antiproliferative effects and inhibitory effects on cyclooxygenases (COX-1 and COX-2). Therefore the invention is also directed to the use of said compounds for the manufacture of a pharmaceutical composition for prevention and treatment of cancer and/or inflammatory diseases. The invention further concerns a method for treating cancer or an inflammatory disease, which comprises the step of administering to a patient suffering from that disease a therapeutically effective amount of at least one of said compounds.

  本发明提供了具有三个苯基的五元杂环，优选吡咯、呋喃和噻吩，其中三个苯基中至少有一个被卤素或三卤甲基取代。本发明的化合物具有抗增殖作用和对环氧化酶（COX-1 和 COX-2）的抑制作用。因此，本发明还涉及使用上述化合物制造预防和治疗癌症和/或炎症性疾病的药物组合物。本发明还涉及一种治疗癌症或炎症性疾病的方法，该方法包括向患有该疾病的患者施用治疗有效量的至少一种所述化合物。
• [EN] TRIPHENYL MODIFIED 5-MEMBERED HETEROCYCLES AND THEIR USE AS ANTICANCER AND ANTIINFLAMMATORY AGENTS<br/>[FR] HÉTÉROCYCLES À 5 CHAÎNONS MODIFIÉS PAR TROIS NOYAUX PHÉNYLE ET LEUR UTILISATION EN TANT QU'AGENTS ANTICANCÉREUX ET ANTI-INFLAMMATOIRES
  申请人：UNIV BERLIN FREIE

  公开号：WO2008006626A1

  公开（公告）日：2008-01-17

  [EN] The present invention provides 5-membered heterooycles, preferably pyrrole furans and thiophenes, with three phenyl moieties wherein at least one of the three Phenyl moieties is substituted with halogen and alkoxy, halogen and hydrox trihalomethy, and alkoxy, trihatomethyl and hydroxy or halogen and alky, an wherein a second phenyl moiety is substituted with at least hydroxy or alkoxy The compounds of the invention show antiproliferative effects and inhibitory effects on cyclooxygenases (COX-1 and COX-2). Therefore the invention is also directed to the use of said compounds for the manufacture of a pharmaceutic composition for prevention and treatment of cancer and/or inflammatory diseases The invention further concerns a method for treating cancer or an inflammator disease, which comprises the step of administering to a patient suffering from that disease a therapeutically effective amount of at least one of said compounds.
  [FR] La présente invention concerne des hétérocycles à 5 chaînons, de préférence des cycles pyrrole, furane et thiophène, comportant trois entités phényle, au moins une des trois entités phényle étant substituée par l'halogène et l'alcoxy, l'halogène et l'hydroxy trihalométhyle, et l'alcoxy, le trihalométhyle et l'hydroxy ou l'halogène et l'alkyl, une seconde entité phényle étant substituée par au moins l'hydroxy ou l'alcoxy. Les composés de l'invention présentent des effets antiprolifératifs et des effets inhibiteurs sur les cyclooxygénases (COX-1 et COX-2). Par conséquent, l'invention concerne également l'utilisation desdits composés pour la fabrication d'une composition pharmaceutique pour la prévention et le traitement du cancer et/ou de maladies inflammatoires. L'invention concerne en outre un procédé de traitement du cancer ou d'une maladie inflammatoire, comprenant l'étape d'administration à un patient souffrant d'une telle maladie d'une quantité efficace du point de vue thérapeutique d'au moins un desdits composés.