2-[(E/Z)-2-(3-methoxyphenyl)vinyl]phenol | 143212-74-2

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 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: 2-[(E/Z)-2-(3-methoxyphenyl)vinyl]phenol
• 英文别名: 1-(2-hydroxyphenyl)-2-(3-methoxyphenyl)ethylene；2-[2-(3-Methoxyphenyl)Ethenyl]Phenol
• CAS: 143212-74-2
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: CKADNPRLDAEDMO-UHFFFAOYSA-N

物化性质

• 沸点：
  379.1±11.0 °C(Predicted)
• 密度：
  1.159

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(E/Z)-2-(3-methoxyphenyl)vinyl]phenol 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 29.0h， 生成 sarpogrelate M-1
  参考文献：
  名称：

  [2-[（ω-氨基烷氧基）苯基]乙基]苯的合成，血小板聚集抑制和抗血栓形成特性。

  摘要：

  合成了一系列的[2-[（ω-氨基氨基烷氧基）苯基]乙基]苯衍生物，并评估了它们在体外抑制胶原蛋白诱导的血小板凝集和保护小鼠血栓形成的能力。结果表明该化合物是胶原诱导的血小板聚集的体外抑制剂。它们中的大多数在小鼠抗血栓形成测定中也有效。发现这些化合物是S2血清素能受体的有效拮抗剂，并且观察到它们的S2血清素能受体拮抗作用与其作为血小板抗凝剂的效力之间具有良好的相关性（r = 0.85）。在研究的化合物中，选择单[2-（二甲基氨基）-1-[[2- [2-（3-（3-甲氧基苯基）乙基]苯氧基]甲基]乙基]琥珀酸酯盐酸盐（12b，MCI-9042）进行进一步的药理和化学反应。毒理学评估。

  DOI：

  10.1021/jm00168a043
• 作为产物：
  描述：

  3-甲氧基氯苄 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 2-[(E/Z)-2-(3-methoxyphenyl)vinyl]phenol
  参考文献：
  名称：

  SAR study on arylmethyloxyphenyl scaffold: Looking for a P-gp nanomolar affinity

  摘要：

  Starting from the previously developed P-gp ligands 1a and 1b (EC50 = 0.25 mu M and 0.65 mu M, respectively), new arylmethyloxyphenyl derivatives have been synthesized as P-gp modulators in order to investigate: (i) the effect of small electron-donor groups (OMe) (5-11), (ii) the effect of the replacement of methoxy groups with an electron-withdrawal substituent (Cl) on C-ring (13) (iii) the effect induced by the replacement of C-ring with heteroaromatic cycles such as thiophene and pyrimidine (13, 15, 16), (iv) the effect induced by molecular constriction on C ring (14,17,18) on P-gp modulating activity. The results demonstrated that P-gp inhibition potency is strongly correlated to the number of methoxy groups in the A-ring whereas the methoxylation of C-ring seems to poorly affect P-gp activity. The best result was found for compound 10 that displays a nanomolar affinity (EC50 = 7.1 nM) towards P-gp pump and, in the meantime lacks of activity against MRP1 pump. (C) 2014 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.02.051

文献信息

• 1-PHENYLALCOXY-2-BETA-PHENYLETHYL DERIVATIVES AS P-GLYCOPROTEIN (P-GP) INHIBITORS USEFUL IN DRUG RESISTANCE EVENTS
  申请人：Berardi Francesco

  公开号：US20090093493A1

  公开（公告）日：2009-04-09

  The invention relates to a new class of compounds, which are 1-phenylalcoxy-2-β-phenylethyl derivatives, as P-glycoprotein (P-GP) inhibitors. These compounds are useful in drug resistance events. They have been shown able to inhibit in a dose-dependent manner Glycoprotein-P (P-gp) activity in cell lines in which the expression of said glycoprotein is very high, like Caco-2 (human colon cancer) cells and MCF7/Adr (adriamycin-resistant human breast carcinoma) cells. The invention also relates to methods of production and the utilization of such compounds as medicaments useful in the treatment of states linked to the difficulty for some drugs to cross the blood-brain barrier (BBB) and generally within the context of the problems of drug resistance induced by chemotherapy agents.

  该发明涉及一类新化合物，即1-苯基羟基-2-β-苯乙基衍生物，作为P-糖蛋白（P-GP）抑制剂。这些化合物在药物耐药事件中很有用。已经证明它们能够以剂量依赖的方式抑制细胞系中的糖蛋白-P（P-gp）活性，其中所述糖蛋白的表达非常高，如Caco-2（人类结肠癌）细胞和MCF7/Adr（阿霉素耐药的人类乳腺癌）细胞。该发明还涉及生产方法和利用这类化合物作为药物的方法，用于治疗与某些药物跨越血脑屏障（BBB）困难相关的状态，以及在化疗药物引起的药物耐药问题背景下的一般情况。
• 一种2-[2-(3-甲氧基-苯基)-乙基]-苯酚的合成 方法
  申请人：千辉药业（安徽）有限责任公司

  公开号：CN104496769B

  公开（公告）日：2016-05-11

  本发明公开了一种2-[2-(3-甲氧基-苯基)-乙基]-苯酚的合成方法，首先合成3-甲氧基苯基磷酸二乙酯和2,2-二甲氧基苯甲醛,然后依次合成1-（2,2-二甲氧基苯基）-2-（3-甲氧基苯基）-乙烯、1-（2-苯酚）-2-（3-甲氧基苯基）-乙烯、1-（2-乙酰氧基苯基）-2-（3-甲氧基苯基）-乙烯合1-（2-乙酰氧基苯基）-2-（3-甲氧基苯基）-乙烷，最后合成2-[2-(3-甲氧基-苯基)-乙基]-苯酚产品。本发明制备的2-[2-(3-甲氧基-苯基)-乙基]-苯酚质量好，收率高。
• Mechanistic Insight into Rh-Catalyzed C(sp²)–O Bond Cleavage Applied to Cross-Coupling Reaction of Benzofurans with Aryl Grignard Reagents
  作者：Takanori Iwasaki、Wataru Ishiga、Shrinwantu Pal、Kyoko Nozaki、Nobuaki Kambe

  DOI：10.1021/acscatal.2c01974

  日期：2022.7.1

  facilitated not only C–O bond cleavage but also the insertion of the C═C bond into the Rh–Ph bond. These strategies and mechanistic insights were successfully applied to develop a strategy for the Rh-catalyzed cross-coupling reaction of fused vinylic ethers, benzofurans, and aryl Grignard reagents, wherein the bond cleavage occurred selectively at the vinylic C(sp2)–O bond, even in the presence of

  本文报道了 Rh 催化的乙烯基醚与芳基格氏试剂通过 C(sp 2 )-O 键断裂发生交叉偶联反应的机理研究。为了获得机理见解，反应在流动反应器中进行，动力学研究表明，对于乙烯基醚和芳基格氏试剂，反应分别服从一级和零级动力学。Rh预催化剂中的烯烃配体对催化性能有显着影响，[RhCl(CH 2 = CH 2 ) 2 ] 2的催化活性约为. 比 [RhCl(cod)] 2高 110 倍. 此外，动力学研究表明，二齿辅助配体 COD 形成了一种休眠物质以减缓催化周转。计算研究表明，由 Rh 预催化剂与两分子芳基格氏试剂反应生成的二芳基铑与乙烯基醚之间的反应是通过 Mg 阳离子辅助插入/抗-β-氧消除而不是氧化加成/还原消除和乙烯基碳上的亲核取代（S N2 伏）。在过渡态中，Mg 抗衡阳离子与基底中的醚氧原子配位，不仅促进了 C-O 键的断裂，而且促进了 C=C 键插入 Rh-Ph 键。这些策略和机
• Arylmethyloxyphenyl Derivatives:  Small Molecules Displaying P-Glycoprotein Inhibition
  作者：Nicola Antonio Colabufo、Francesco Berardi、Roberto Perrone、Simona Rapposelli、Maria Digiacomo、Aldo Balsamo

  DOI：10.1021/jm060639z

  日期：2006.11.1

  Some arylmethyloxyphenyl derivatives were prepared as simplified structures of analogous arylpiperazines with high affinity toward dopaminergic D-2 and serotonergic 5-HT1A receptors and inhibiting P-glycoprotein (P-gp). The compounds 5b and 8b displayed good P-gp inhibition activity measured as [H-3] vinblastine transport inhibition in the Caco-2 cell monolayer and intracellular doxorubicin accumulation in MCF7/Adr cells by flow cytometry. Compounds 5b and 8b also inhibited, dose-dependently, ATP-ase activation induced by P-gp substrate vinblastine.
• Syntheses and platelet aggregation inhibitory and antithrombotic properties of [2-[(.omega.-Aminoalkoxy)phenyl]benzenes
  作者：Ryoji Kikumoto、Hiroto Hara、Kunihiro Ninomiya、Masanori Osakabe、Mamoru Sugano、Harukazu Fukami、Yoshikuni Tamao

  DOI：10.1021/jm00168a043

  日期：1990.6

  A series of [2-[(omega-aminoalkoxy)phenyl]ethyl]benzene derivatives were synthesized and evaluated for their ability to inhibit collagen-induced platelet aggregation in vitro and to protect experimental thrombosis in mice. The results showed that the compounds were in vitro inhibitors of collagen-induced platelet aggregation. Most of them were also effective in the mouse antithrombotic assay. The compounds

  合成了一系列的[2-[（ω-氨基氨基烷氧基）苯基]乙基]苯衍生物，并评估了它们在体外抑制胶原蛋白诱导的血小板凝集和保护小鼠血栓形成的能力。结果表明该化合物是胶原诱导的血小板聚集的体外抑制剂。它们中的大多数在小鼠抗血栓形成测定中也有效。发现这些化合物是S2血清素能受体的有效拮抗剂，并且观察到它们的S2血清素能受体拮抗作用与其作为血小板抗凝剂的效力之间具有良好的相关性（r = 0.85）。在研究的化合物中，选择单[2-（二甲基氨基）-1-[[2- [2-（3-（3-甲氧基苯基）乙基]苯氧基]甲基]乙基]琥珀酸酯盐酸盐（12b，MCI-9042）进行进一步的药理和化学反应。毒理学评估。