methyl 3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-enoate | 1141446-31-2

• 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: methyl 3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-enoate
• CAS: 1141446-31-2
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: LXXJVRREPUUSGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-enoate 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到methyl 2,3,6-trimethoxyphenanthrene-9-carboxylate
  参考文献：
  名称：

  Seven- and eight-membered heterocyclic biaryl synthesis through a metal-free oxidative coupling reaction

  摘要：

  A metal-free intramolecular biaryl coupling mediated by DDQ and BF3 center dot OEt2 was developed. The reaction proceeds smoothly at room temperature to give seven- and eight-membered heterocyclic biaryl compounds in up to 95% yields. Only 1 equiv of DDQ sufficed for the reaction, obviating the use of a large excess of oxidants and undesired chlorination pathway in metal-mediated process. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.103
• 作为产物：
  描述：

  (Z)-3,4-dimethoxy-α-(4-methoxyphenyl)cinnamic acid 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到methyl 3-(3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  NOVEL HISTONE DEACETYLASE INHIBITORS

  摘要：

  本文提供了一种新型的类荧光素化合物，其通式为(I)，以及它们的衍生物、类似物、互变异构体、立体异构体、多晶形、水合物、代谢产物、前药、溶剂化物、药学上可接受的盐和组合物。这些化合物可以抑制HDACs，并且可用作治疗或改善细胞生长相关疾病的治疗剂，例如恶性肿瘤、自身免疫疾病、皮肤病、感染、炎症等。

  公开号：

  US20100222379A1

文献信息

• Histone deacetylase inhibitors
  申请人：Rajagopal Sridharan

  公开号：US08476255B2

  公开（公告）日：2013-07-02

  Provided herein are novel, stilbene like compounds of the general formula (I), their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, metabolites, prodrugs, solvates, pharmaceutically acceptable salts and compositions thereof. These compounds can inhibit HDACs and are useful as a therapeutic or ameliorating agent for diseases that are involved in cellular growth such as malignant tumors, autoimmune diseases, skin diseases, infections, inflammation, etc.

  本文提供一种新型的还原苯乙烯类化合物，其通式为(I)，以及它们的衍生物、类似物、互变异构体、立体异构体、多晶形、水合物、代谢物、前药、溶剂合物、药学上可接受的盐和组合物。这些化合物可以抑制组蛋白去乙酰化酶，并且可用作治疗或改善细胞生长相关的疾病的药物，如恶性肿瘤、自身免疫性疾病、皮肤病、感染、炎症等。
• Synthesis and Biological Activity of Some Bromophenols and Their Derivatives Including Natural Products
  作者：Cetin Bayrak、Parham Taslimi、Namik Kilinc、Ilhami Gulcin、Abdullah Menzek

  DOI：10.1002/cbdv.202300469

  日期：2023.8

  In addition to the first synthesis of the natural bromophenol butyl 2-(3,5-dibromo-4-hydroxyphenyl)acetate (1), indene derivatives 34 and 35 were synthesized from 3-phenylpropenal derivatives in BBr3 medium. Five known natural bromophenols and some derivatives were synthesized by known methods. Cholinesterase (ChEs) inhibitors reduce the breakdown of acetylcholine and are used in the treatment of Alzheimer's

  除了首次合成天然溴苯酚2-(3,5-二溴-4-羟基苯基)乙酸丁酯( 1 )之外，还在BBr 3介质中由3-苯基丙烯醛衍生物合成了茚衍生物34和35。通过已知方法合成了五种已知的天然溴苯酚和一些衍生物。胆碱酯酶 (ChEs) 抑制剂可减少乙酰胆碱的分解，用于治疗阿尔茨海默病 (AD) 和痴呆症状。检测了所有获得的化合物对乙酰胆碱酯酶（AChE）、丁酰胆碱酯酶（BChE）和α-糖苷酶的抑制作用。所有合成的化合物均表现出对两种胆碱能酶的强烈抑制作用。为了测定新型溴酚的 Ki 值，获得了 Lineweaver-Burk 图。AChE 的 Ki 值范围为 0.13–14.74 nM，BChE 的 Ki 值范围为 5.11–23.95 nM，α-糖苷酶的 Ki 值范围为 63.96–206.78 nM。与阳性对照相比，所有溴酚及其衍生物均表现出有效的抑制特性。
• [EN] NOVEL HISTONE DEACETYLASE INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DES HISTONE DÉSACÉTYLASES
  申请人：ORCHID RES LAB LTD

  公开号：WO2009047615A3

  公开（公告）日：2010-07-01
• Seven- and eight-membered heterocyclic biaryl synthesis through a metal-free oxidative coupling reaction
  作者：Shutao Sun、Jingjing Yang、Fanmei Li、Zheng Lv、Wei Li、Hongxiang Lou、Lei Liu

  DOI：10.1016/j.tetlet.2014.10.103

  日期：2014.12

  A metal-free intramolecular biaryl coupling mediated by DDQ and BF3 center dot OEt2 was developed. The reaction proceeds smoothly at room temperature to give seven- and eight-membered heterocyclic biaryl compounds in up to 95% yields. Only 1 equiv of DDQ sufficed for the reaction, obviating the use of a large excess of oxidants and undesired chlorination pathway in metal-mediated process. (C) 2014 Elsevier Ltd. All rights reserved.
• NOVEL HISTONE DEACETYLASE INHIBITORS
  申请人：Rajagopal Sridharan

  公开号：US20100222379A1

  公开（公告）日：2010-09-02

  Provided herein are novel, stilbene like compounds of the general formula (I), their derivatives, analogs, tautomeric forms, stereoisomers, polymorphs, hydrates, metabolites, prodrugs, solvates, pharmaceutically acceptable salts and compositions thereof. These compounds can inhibit HDACs and are useful as a therapeutic or ameliorating agent for diseases that are involved in cellular growth such as WO 2009/047615 A2 malignant tumors, autoimmune diseases, skin diseases, infections, inflammation, etc.

  本文提供了一种新型的类荧光素化合物，其通式为(I)，以及它们的衍生物、类似物、互变异构体、立体异构体、多晶形、水合物、代谢产物、前药、溶剂化物、药学上可接受的盐和组合物。这些化合物可以抑制HDACs，并且可用作治疗或改善细胞生长相关疾病的治疗剂，例如恶性肿瘤、自身免疫疾病、皮肤病、感染、炎症等。