(2E,4E)-ethyl 5-(3,4-dimethoxyphenyl)penta-2,4-dienoate | 101619-71-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E)-ethyl 5-(3,4-dimethoxyphenyl)penta-2,4-dienoate
• 英文别名: ethyl (2E,4E)-5-(3,4-dimethoxyphenyl)penta-2,4-dienoate
• CAS: 101619-71-0
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: RSDUMKBVRIVBPA-KQQUZDAGSA-N

物化性质

• 沸点：
  403.5±35.0 °C(Predicted)
• 密度：
  1.085±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E,4E)-ethyl 5-(3,4-dimethoxyphenyl)penta-2,4-dienoate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 生成 5-(3,4-dimethoxyphenyl)penta-(2E,4E)-dienoic acid
  参考文献：
  名称：

  合成冯Alkylphenolen UND -pyrocatecholen AUS之左手球酵母（唇形科）

  摘要：

  从白花香（Labiatae）合成烷基酚和邻苯二酚

  DOI：

  10.1002/hlca.19930760509
• 作为产物：
  描述：

  1-(3,4-二甲氧基苯基)乙醇 在 sodium hydride 、 三氯氧磷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 生成 (2E,4E)-ethyl 5-(3,4-dimethoxyphenyl)penta-2,4-dienoate
  参考文献：
  名称：

  Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities

  摘要：

  Inhibitors of drug metabolism have important implications in pharmaco-toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modifications in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC- and PB- treated rat liver in vitro. Modifications were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure-activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modification in either of the three components of piperine. Saturation of the side chain resulted in significantly enhanced inhibition of CYP while modifications in the phenyl and basic moieties in few analogues offered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus Few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00273-4

文献信息

• Copper-catalyzed C–S direct cross-coupling of thiols with 5-arylpenta-2,4-dienoic acid ethyl ester
  作者：Rongrong Cai、Zhuoda Zhou、Qianqian Chai、Yueer Zhu、Runsheng Xu

  DOI：10.1039/c8ra05311a

  日期：——

  A selective copper (Cu)-catalyzed C–S bond direct cross-coupling of thiols with 5-arylpenta-2,4-dienoic acid ethyl ester was developed. Notably, various biologically active 5-phenyl-3-phenylsulfanylpenta-2,4-dienoic acid ethyl ester derivatives were efficiently synthesized under moderate conditions. Finally, a plausible Cu(I)/Cu(III) reaction mechanism was proposed.

  开发了选择性铜 (Cu) 催化的 C-S 键直接交叉偶联硫醇与 5-arylpenta-2,4-二烯酸乙酯。值得注意的是，各种具有生物活性的 5-苯基-3-苯基硫烷基五-2,4-二烯酸乙酯衍生物在温和条件下被高效合成。最后，提出了一种似是而非的Cu( I )/Cu( III )反应机理。
• New potent and selective polyfluoroalkyl ketone inhibitors of GVIA calcium-independent phospholipase A2
  作者：Victoria Magrioti、Aikaterini Nikolaou、Annetta Smyrniotou、Ishita Shah、Violetta Constantinou-Kokotou、Edward A. Dennis、George Kokotos

  DOI：10.1016/j.bmc.2013.07.010

  日期：2013.9

  Group VIA calcium-independent phospholipase A2 (GVIA iPLA2) has recently emerged as an important pharmaceutical target. Selective and potent GVIA iPLA2 inhibitors can be used to study its role in various neurological disorders. In the current work, we explore the significance of the introduction of a substituent in previously reported potent GVIA iPLA2 inhibitors. 1,1,1,2,2-Pentafluoro-7-(4-methox

  VIA 组钙非依赖性磷脂酶 A 2 (GVIA iPLA 2 ) 最近已成为重要的药物靶点。选择性和有效的 GVIA iPLA 2抑制剂可用于研究其在各种神经系统疾病中的作用。在目前的工作中，我们探讨了在先前报道的强效 GVIA iPLA 2抑制剂中引入取代基的重要性。1,1,1,2,2-五氟-7-(4-甲氧基苯基)庚烷-3-one (GK187) 是有史以来报告的最有效和选择性的 GVIA iPLA 2抑制剂，其X I (50) 值为 0.0001，并且对 GIVA cPLA 2或 GV sPLA 2没有显着抑制作用. 我们还比较了两种二氟甲基酮对 GVIA iPLA 2、GIVA cPLA 2和 GV sPLA 2的抑制作用。
• (2E,4E)-N-(4-(1H-Indol-3-yl)piperidin-1-yl)alkyl-5-(substituted phenyl)-2,4-pentadienamides as Antiallergic Agents with Antihistaminic and Anti Slow-Reacting Substance (SRS) Activities
  作者：Shinji Shigenaga、Takashi Manabe、Hiroshi Matsuda、Takashi Fujii、Masaaki Matsuo

  DOI：10.1002/ardp.19963290103

  日期：——

  compound with dual activities against histamine and slow‐reacting substance (SRS), we synthesized two types of indolylpiperidine derivatives, 3 and 4–20. Testing for in vivo antianaphylactic activity and for in vitro anti‐SRS activity revealed that (2E,4E)‐5‐(3,5‐dimethoxy‐4‐hydroxyphenyl)‐N‐(2‐(4‐(1H‐indol‐3‐yl)piperidin‐1‐yl)ethyl)‐2,4‐pentadienamide (11) exhibited potent dual activities with ED50 = 0

  作为我们研究的延伸，旨在发现一种对组胺和慢反应物质 (SRS) 具有双重活性的新型化合物，我们合成了两种类型的吲哚哌啶衍生物，3 和 4-20。体内抗过敏活性和体外抗 SRS 活性测试表明 (2E, 4E) -5- (3,5 - 二甲氧基 - 4 - 羟基苯基) -N- (2- (4- (1H - indole - 3 ‐Yl) 哌啶 ‐ 1 ‐ yl) 乙基) ‐2,4 - 戊二烯酰胺 (11) 表现出有效的双重活性，分别为 ED50 = 0.89 mg / kg 和 IC50 = 1.43 μM。然而，当在豚鼠中口服给药时，未改变的 11 的血浆浓度非常低。这一结果可以通过快速形成葡萄糖醛酸结合物来解释。