5-<4-(benzyloxy)-3-methoxyphenyl>-2,4-pentadienoic acid | 102018-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-<4-(benzyloxy)-3-methoxyphenyl>-2,4-pentadienoic acid
• 英文别名: 5-(4-benzyloxy-3-methoxyphenyl)-2E,4E-pentadienoic acid；5-[3-methoxy-4-(benzyloxy)phenyl]-2,4-pentadienoic acid；5-(4-Benzyloxy-3-methoxyphenyl)-2,4-pentadienoic acid；5-[4-(benzyloxy)-3-methoxyphenyl]-2,4-pentadienoic acid；(2E,4E)-5-(3-methoxy-4-phenylmethoxyphenyl)penta-2,4-dienoic acid
• CAS: 102018-94-0
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: QFGKFUXIYCPRDG-YLNKAEQOSA-N

物化性质

• 沸点：
  524.5±45.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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-<4-(benzyloxy)-3-methoxyphenyl>-2,4-pentadienoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 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：

  (E)-3-(4-(benzyloxy)-3-methoxyphenyl)acrylaldehyde 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-<4-(benzyloxy)-3-methoxyphenyl>-2,4-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

• Pharmacologically active compounds, methods for the preparation thereof
  申请人：Orion-yhtyma Oy

  公开号：US04963590A1

  公开（公告）日：1990-10-16

  Pharmacologically active catechol derivatives of formula I ##STR1## wherein R.sub.1 and R.sub.2 independently comprise hydrogen, alkyl, acyl, optionally substituted aroyl, lower alkylsulfonyl or alkylcabamoyl or taken together form a lower alkylidene or cycloalkylidene, X comprises an electronegative substituent such as halogen, nitro, cyano, lower alkylsulfonyl, sulfonamido, aldehyde, caboxyl or trifluoromethyl and R.sub.3 comprises hydrogen, halogen, hydroxy alkyl, amino, nitro, cyano, trifluoromethyl, lower alkylsulfonyl, sulfonamide, aldehyde, alkyl carbonyl, aralkylidene carbonyl or carboxyl or a group selected from ##STR2## wherein R.sub.4 comprises hydrogen, alkyl, cyano, carboxyl or acyl and R.sub.5 comprises hydrogen, cyano, carboxyl, alkoxycarbonyl, carboxyalkenyl, nitro, acyl, optionally substituted aroyl or heteroaroyl, hydroxyalkyl or carboxyalkyl or R.sub.4 and R.sub.5 together form a five to seven membered substituted cycloalkanone ring; --(CO).sub.n (CH.sub.2).sub.m --COR wherein n is 0-1 and m is 0-7 and R comprises hydroxy, alkyl, carboxyalkyl, optionally substituted alkene, alkoxy or optionally substituted amino; ##STR3## wherein R.sub.8 and R.sub.9 independently comprise hydrogen or one of the following optionally substituted groups; alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl, or together form an optionally substituted piperidyl group; --NH--CO--R.sub.10 wherein R.sub.10 comprises a substituted alkyl group.

  公式I的药理活性儿茶酚衍生物，其中R.sub.1和R.sub.2独立地包括氢、烷基、酰基、可选择地取代的芳酰基、较低的烷基磺酰基或烷基氨基甲酰基，或者一起形成较低的烷基亚甲基或环烷基亚甲基，X包括电负取代基，如卤素、硝基、氰基、较低的烷基磺酰基、磺胺基、醛基、羧基或三氟甲基，R.sub.3包括氢、卤素、羟基烷基、氨基、硝基、氰基、三
• Synthesis of some novel potent and selective catechol O-methyltransferase inhibitors
  作者：Reijo Backstrom、Erkki Honkanen、Aino Pippuri、Pekka Kairisalo、Jarmo Pystynen、Kalevi Heinola、Erkki Nissinen、Inge Britt Linden、Pekka T. Mannisto

  DOI：10.1021/jm00124a017

  日期：1989.4

  A series of disubstituted catechol derivatives was synthesized and tested as potential COMT inhibitors. The most active compounds were more than 1000 times more potent (IC50 = 3-6 nM) in vitro than the known COMT inhibitor, 3',4'-dihydroxy-2-methylpropiophenone (U 0521, IC50 = 6000 nM). The new compounds were also highly selective COMT inhibitors with no activity against other essential enzymes involved

  合成了一系列二取代的邻苯二酚衍生物，并测试了其作为潜在的COMT抑制剂的能力。活性最高的化合物在体外的效价（IC50 = 3-6 nM）比已知的COMT抑制剂3'，4'-二羟基-2-甲基苯乙酮（U 0521，IC50 = 6000 nM）高出1000倍以上。新化合物也是高度选择性的COMT抑制剂，对儿茶酚胺的合成和代谢中涉及的其他必需酶没有活性。
• Amide derivatives and antiallergic agents containing the same
  申请人：Terumo Kabushiki Kaisha

  公开号：US04859673A1

  公开（公告）日：1989-08-22

  Novel amide derivatives are disclosed. As examples of said amide derivatives are mentioned 1-[2-(5-(3-methoxy-4-benzyloxyphenyl)-2,4-pentadienoyl)aminoethyl]-4-diphe nylmethoxypiperidine, 1-[2-(5-(3-methoxy-4-pentadienoyl)aminoethyl]-4-diphenylmethoxypiperidine and 1-[2-(5-(3-methoxy-4-ethoxymethoxyphenyl)-2,4-pentadienoyl)aminoethyl]-4-d iphenylmethoxypiperidine. These amide derivatives are useful as antiallergic agents.

  本发明涉及新的酰胺衍生物。其中所述的酰胺衍生物的例子包括1-[2-(5-(3-甲氧基-4-苄氧基苯基)-2,4-戊二烯酰)氨基乙基]-4-二苯甲氧基哌啶、1-[2-(5-(3-甲氧基-4-戊二烯酰)氨基乙基]-4-二苯甲氧基哌啶和1-[2-(5-(3-甲氧基-4-乙氧甲氧基苯基)-2,4-戊二烯酰)氨基乙基]-4-二苯甲氧基哌啶。这些酰胺衍生物可用作抗过敏剂。
• NOVEL COMPOUNDS AND USE THEREOF AS MEDICINE
  申请人：TSUMURA & CO.

  公开号：EP0535250A1

  公开（公告）日：1993-04-07

  Specified cinnamic acid derivatives, such as methyl 4-(4-acetoxy-3-methoxycinnamamide)-1-methyl-1-cyclohexanecarboxylate, and pharmaceutically acceptable salts thereof, which are useful as an allergy type IV reaction inhibitor.

  特定肉桂酸衍生物，如 4-(4-乙酰氧基-3-甲氧基肉桂酰胺)-1-甲基-1-环己烷羧酸甲酯及其药学上可接受的盐，可用作 IV 型过敏反应抑制剂。
• New cannamide derivatives and their use as allergy inhibitors
  申请人：TSUMURA & CO.

  公开号：EP0705817A1

  公开（公告）日：1996-04-10

  New cinnamic acid derivatives, such as methyl 4-(4-acetoxy-3-methoxycinnamanide)-1-cyclohexanecarboxylate, and pharmaceutically acceptable salts thereof, are useful as IV-type allergic reaction-suppressive drugs.

  新型肉桂酸衍生物，如 4-(4-乙酰氧基-3-甲氧基肉桂酸)-1-环己烷羧酸甲酯及其药学上可接受的盐类，可用作 IV 型过敏反应抑制药物。