(E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoyl chloride | 203722-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoyl chloride
• 英文别名: 5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl chloride；(2E,4E)-5-(3,4,5-trimethoxyphenyl)penta-2,4-dienoyl chloride
• CAS: 203722-02-5
• 化学式: C₁₄H₁₅ClO₄
• 分子量: 282.724
• InChiKey: HYNNSZLTBDCVCP-YDFGWWAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  哌啶 、 (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoyl chloride 以 二氯甲烷 为溶剂， 反应 0.5h， 以1.86 g的产率得到(2E,4E)-1-(piperidin-1-yl)-5-(3,4,5-trimethoxyphenyl)penta-2,4-dien-1-one
  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
• 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 、 氯化亚砜 、 sodium hydride 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (E,E)-5-(3,4,5-trimethoxyphenyl)-2,4-pentadienoyl chloride
  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。
• Diamide compound and drugs containing the same
  申请人：Kowa Co., Ltd.

  公开号：US06340682B1

  公开（公告）日：2002-01-22

  The present invention provides diamide derivatives represented by the following general formula (1): wherein A is a phenyl group or the like, which may be substituted, B is —CH═CH—, —C═C—, —(CH═CH)2—, —C≡C—CH═CH—, —CH═CH—C≡C—, phenylene or the like, and W is or 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。
• Structure–Activity Relationship of Piplartine and Synthetic Analogues against Schistosoma mansoni and Cytotoxicity to Mammalian Cells
  作者：Yuri Campelo、Alicia Ombredane、Andreanne Vasconcelos、Lucas Albuquerque、Daniel Moreira、Alexandra Plácido、Jefferson Rocha、Harold Hilarion Fokoue、Lydia Yamaguchi、Ana Mafud、Yvonne Mascarenhas、Cristina Delerue-Matos、Tatiana Borges、Graziella Joanitti、Daniel Arcanjo、Massuo Kato、Selma Kuckelhaus、Marcos Silva、Josué Moraes、José Leite

  DOI：10.3390/ijms19061802

  日期：——

  1M, 14B and 6B) against Schistosoma mansoni adult worms, as well as its cytotoxicity to mammalian cells using murine fibroblast (NIH-3T3) and BALB/cN macrophage (J774A.1) cell lines. In addition, density functional theory calculations and in silico analysis were used to predict physicochemical and toxicity parameters. Bioassays revealed that piplartine is active against S. mansoni at low concentrations

  血吸虫病是由血吸虫属的蠕虫扁虫引起的，是一种主要与贫困相关的传染病，影响了全世界数百万人。由于该疾病的治疗仅依赖于吡喹酮的使用，因此迫切需要鉴定新的抗血吸虫病药物。Piplartine是一种酰胺生物碱，存在于几种Piper物种（Piperaceae）中，具有抗血吸虫病的特性。这项研究的目的是评估piplartine及其五种合成类似物（19A，1G，1M，14B和6B）对曼氏血吸虫成虫的结构-功能关系，以及使用鼠成纤维细胞（NIH）对哺乳动物细胞的细胞毒性-3T3）和BALB / cN巨噬细胞（J774A.1）细胞系。此外，密度泛函理论计算和计算机分析用于预测理化和毒性参数。生物测定表明，吡普拉汀在低浓度（5×10 µM）下对曼氏链球菌有活性，但其类似物却没有。相比之下，基于3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物（MTT）和流式细胞术测定，吡普拉汀在785 µM的哺乳动
• [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。