5-(2,3-dihydrobenzo[1,4]dioxin-6-yl)penta-2,4-dienoic acid | 261913-25-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 5-(2,3-dihydrobenzo[1,4]dioxin-6-yl)penta-2,4-dienoic acid
• 英文别名: 5-(3,4-ethylenedioxyphenyl)-2E,4E-pentadienoic acid；(2E,4E)-5-(2,3-dihydro-1,4-benzodioxin-6-yl)penta-2,4-dienoic acid
• CAS: 261913-25-1
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: KNMBFTABPHRNAS-ZPUQHVIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2,3-dihydrobenzo[1,4]dioxin-6-yl)penta-2,4-dienoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成
  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：

  1,4-苯并二恶烷-6-甲醛 在 双(三甲基硅烷基)氨基钾 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 4.67h， 生成 5-(2,3-dihydrobenzo[1,4]dioxin-6-yl)penta-2,4-dienoic acid
  参考文献：
  名称：

  Naphthalene and 2,3-dihydrobenzo[b][1,4]dioxine derivatives with extended side chains as new scaffolds of CB₂-selective ligands

  摘要：

  在这里，我们报告了合成具有延长侧链的萘、二氢苯并二恶烷和芴衍生物，并对它们进行了作为CB₁和CB₂受体配体的生物评价。

  DOI：

  10.1039/c4md00232f

文献信息

• Novel substituted aryl alkenoic acid heterocyclic amides
  申请人：Taneja Chandra Subhash

  公开号：US20060094874A1

  公开（公告）日：2006-05-04

  The present invention relates to novel compounds possessing specific hot, pungent and spicy taste when subjected to direct pungency evaluation, which may be useful as food additives and anti-oxidants, however the said compounds do not add to any nutritional value but the synthesised compounds can possess useful pharmacological properties which is expected to find application in new test models for the development of anti-inflammatory drugs, bioavailability enhancers and for the study of hepatic drug metabolising mechanism; also relates to a process for preparing the said compounds.

  本发明涉及一种新型化合物，当直接进行辛辣度评估时，具有特定的热辣、刺激和辛辣的口感，可用作食品添加剂和抗氧化剂，但该化合物不会增加任何营养价值，但合成的化合物可以具有有用的药理学性质，预计可在新的测试模型中应用于抗炎药物、生物利用度增强剂的开发和肝脏药物代谢机制的研究；同时涉及一种制备该化合物的方法。
• QUINOLONE DERIVATIVE
  申请人：Onda Kenichi

  公开号：US20100256113A1

  公开（公告）日：2010-10-07

  As a result of extensive studies on NAD(P)H oxidase inhibitors, the present inventors found that a quinolone derivative having, at the 2-position, an alkyl group substituted with a heteroatom or the like has an excellent NAD(P)H oxidase inhibitory activity, and accomplished the present invention. The compound of the present invention has a reactive oxygen species production inhibitory activity based on the NAD(P)H oxidase inhibitory activity, and therefore can be used as an agent for preventing and/or treating diabetes, impaired glucose tolerance, hyperlipidemia, fatty liver, diabetic complications and the like.

  通过对NAD（P）H氧化酶抑制剂的广泛研究，本发明人发现，在2位具有被杂原子或类似物取代的烷基的喹诺酮衍生物具有优异的NAD（P）H氧化酶抑制活性，并完成了本发明。本发明的化合物具有基于NAD（P）H氧化酶抑制活性的反应性氧化物产生抑制活性，因此可用作预防和/或治疗糖尿病、糖耐量受损、高脂血症、脂肪肝、糖尿病并发症等代理。
• US8367702B2
  申请人：——

  公开号：US8367702B2

  公开（公告）日：2013-02-05
• Structure–activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities
  作者：Surrinder Koul、Jawahir L. Koul、Subhash C. Taneja、Kanaya L. Dhar、Deshvir S. Jamwal、Kuldeep Singh、Rashmeet K. Reen、Jaswant Singh

  DOI：10.1016/s0968-0896(99)00273-4

  日期：2000.1

  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.
• Naphthalene and 2,3-dihydrobenzo[b][1,4]dioxine derivatives with extended side chains as new scaffolds of CB₂-selective ligands
  作者：Noha A. Osman、Amr H. Mahmoud、Christian D. Klein、Marco Allarà、Vincenzo Di Marzo、Khaled M. Abouzid、Ashraf H. Abadi

  DOI：10.1039/c4md00232f

  日期：——

  Herein, we report the synthesis of naphthalene, dihydrobenzodioxine and fluorene derivatives with extended side chains and their biological evaluation as ligands of CB₁ and CB₂ receptors.

  在这里，我们报告了合成具有延长侧链的萘、二氢苯并二恶烷和芴衍生物，并对它们进行了作为CB₁和CB₂受体配体的生物评价。