5-(3,4,5-trimethoxyphenyl)-2E,4E-pentadienoic acid | 28010-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3,4,5-trimethoxyphenyl)-2E,4E-pentadienoic acid
• 英文别名: (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid；5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoic acid；5-(3,4,5-trimethoxyphenyl)-2,4-pentadienic acid；5t-(3,4,5-trimethoxy-phenyl)-penta-2t,4-dienoic acid；5t-(3,4,5-Trimethoxy-phenyl)-penta-2t,4-diensaeure；5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoic acid；(2E,4E)-5-(3,4,5-trimethoxyphenyl)penta-2,4-dienoic acid
• CAS: 28010-23-3
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: WQIHERMZQSQZPC-YDFGWWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3,4,5-trimethoxyphenyl)-2E,4E-pentadienoic acid 在 草酰氯 作用下， 以 DMF (N,N-dimethyl-formamide) 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoyl chloride
  参考文献：
  名称：

  Diamide compound and drugs containing the same

  摘要：

  本发明提供了以下一般式（1）所代表的二酰胺衍生物： 其中A是苯基或类似物，可以被取代，B是—CH═CH—，—C═C—，—(CH═CH)2—，—C≡C—CH═CH—，—CH═CH—C≡C—，苯基或类似物，W是 或 以及包含这种化合物的药物。这些化合物对IgE抗体的产生具有出色的抑制作用，因此可用作抗过敏药物等。

  公开号：

  US06340682B1
• 作为产物：
  描述：

  (2E)-3-(3,4,5-三甲氧基苯基)丙烯醛 在 氢氧化钾 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 反应 6.0h， 生成 5-(3,4,5-trimethoxyphenyl)-2E,4E-pentadienoic acid
  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

• Cyclic amide compound
  申请人：KOWA CO., LTD.

  公开号：US20030096828A1

  公开（公告）日：2003-05-22

  The invention relates to compounds represented by the following general formula (1): 1 wherein A is an aromatic compound which may be substituted, or the like, B is a nitrogen atom or CH, X is a lower alkylene group which may be substituted, or the like, Yi s a single bond or the like; Z is a divalent residue of benzene which may be substituted, or the like, and m and n are independently an integer of 1 to 4, and medicines comprising such a compound. These compounds have an excellent inhibitory effect on the production of an IgE antibody and are hence useful as antiallergic agents and the like.

  该发明涉及由以下一般式（1）表示的化合物： 1 其中A是可能被取代的芳香化合物，B是氮原子或CH等，X是可能被取代的较低烷基基团，Y是单键等；Z是可能被取代的苯的二价残基，m和n分别是1到4的整数，以及包含这种化合物的药物。这些化合物对IgE抗体的产生具有出色的抑制作用，因此可用作抗过敏药物等。
• Diamide compounds and compositions containing the same
  申请人：Kowa Co., Ltd.

  公开号：US06297283B1

  公开（公告）日：2001-10-02

  The present invention relates to compounds represented by the following general formula (1): wherein A is a phenyl, naphthyl, dihydronaphthyl, indenyl, pyridyl, indolyl, isoindolyl, quinolyl or isoquinolyl group which may be substituted; X is a lower alkylene group which may be substituted, or the like; Y is a single bond or an alkylene group; Z is a group of —CH═CH—, —C≡C—, —(CH═CH)2—, —C≡C—CH═CH— or —CH═CH—C≡C—, or the like; and R is a hydrogen atom, a lower alkyl group or the like, and medicines comprising such a compound. These compounds have an excellent inhibitory effect on the production of an IgE antibody and are hence useful as antiallergic agents and the like.

  本发明涉及以下一般式（1）所代表的化合物： 其中A是苯基、萘基、二氢萘基、茚基、吡啶基、吲哚基、异吲哚基、喹啉基或异喹啉基，可以被取代；X是可以被取代的较低烷基烯基，或类似物；Y是单键或烷基烯基；Z是—CH═CH—、—C≡C—、—(CH═CH)2—、—C≡C—CH═CH—或—CH═CH—C≡C—等基团；R是氢原子、较低烷基基团或类似物，以及包含这种化合物的药物。这些化合物对IgE抗体的产生具有出色的抑制作用，因此可用作抗过敏药物等。
• Diene derivatives and vasodilators containing the same
  申请人：Terumo Kabushiki Kaisha

  公开号：US04792553A1

  公开（公告）日：1988-12-20

  Novel dienyl derivatives are disclosed. As examples of said diene derivative are mentioned 1-benzhydryl-4-(5-phenyl-2,4-pentadienyl)piperazine, 1-(4,4'-difluorobenzhydryl)-4-(5-phenyl-2,4-pentadienyl)piperazine, 1-benzhydryl-4-(5-(3,4,5-trimethoxyphenyl)-2,4-pentadienyl)piperazine, 1-(4,4'-difluorobenzhydryl)-4-(5-(2,4-dimethoxyphenyl)-2,4-pentadienyl)pip erazine, 1-benzhydryl-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienyl)piperazine, 1-(4,4'-difluorobenzhydryl)-4-(5-(2,3,4-trimethoxyphenyl)-2,4-pentadienyl) piperazine and the like. These dienyl derivatives are useful as vasodilators.

  披露了新颖的二烯基衍生物。作为所述二烯衍生物的示例，提到了1-苯甲基-4-(5-苯基-2,4-戊二烯基)哌嗪、1-(4,4'-二氟苯甲基)-4-(5-苯基-2,4-戊二烯基)哌嗪、1-苯甲基-4-(5-(3,4,5-三甲氧基苯基)-2,4-戊二烯基)哌嗪、1-(4,4'-二氟苯甲基)-4-(5-(2,4-二甲氧基苯基)-2,4-戊二烯基)哌嗪、1-苯甲基-4-(5-(2,3,4-三甲氧基苯基)-2,4-戊二烯基)哌嗪、1-(4,4'-二氟苯甲基)-4-(5-(2,3,4-三甲氧基苯基)-2,4-戊二烯基)哌嗪等。这些二烯基衍生物可用作血管扩张剂。
• [EN] NOVEL PIPERINE DERIVATIVES AS GABA - A RECEPTORS MODULATORS<br/>[FR] NOUVEAUX DÉRIVÉS PIPÉRINES COMME MODULATEURS DES RÉCEPTEURS GABA - A
  申请人：UNIV WIEN

  公开号：WO2011080313A1

  公开（公告）日：2011-07-07

  The present invention encompasses novel piperin compounds of general formula (I) wherein R1, R2, R3, m and n are defined as in claim 1, which are suitable for the prevention and/or treatment of diseases mediated by modulation of GABAA receptor and the use thereof for preparing a medicament having the above mentioned properties.

  本发明涵盖了一种新型的辣椒素化合物，其一般化学式为（I），其中R1、R2、R3、m和n的定义如索赔1所述，适用于通过调节GABAA受体来预防和/或治疗由此介导的疾病，并用于制备具有上述特性的药物。
• (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。