(2E,4E)-5-(4-methoxyphenyl)-1-(4-methylpiperazine-1-yl)penta-2,4-dien-1-one | 261913-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,4E)-5-(4-methoxyphenyl)-1-(4-methylpiperazine-1-yl)penta-2,4-dien-1-one
• 英文别名: (2E,4E)-5-(4-methoxyphenyl)-1-(4-methylpiperazin-1-yl)penta-2,4-dien-1-one
• CAS: 261913-02-4
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: FFUVDUDESJRGEK-GGWOSOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(4-methoxyphenyl)-1-(4-methylpiperazine-1-yl)penta-2,4-dien-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以93%的产率得到5-(4-methoxyphenyl)pentanoic acid N-methylpiperazine amide
  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,4E)-5-(4-methoxyphenyl)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 (2E,4E)-5-(4-methoxyphenyl)-1-(4-methylpiperazine-1-yl)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

文献信息

• (2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-ONE DERIVATIVE
  申请人：BIOWAY., INC

  公开号：US20200157048A1

  公开（公告）日：2020-05-21

  The present application relates to a novel pentadienoyl compound and a pharmaceutical composition including the same. The pentadienoyl compound of the present application may be used to prevent or treat fatty liver and fatty liver-related disease by inhibiting lipogenesis and lipid accumulation in cells and activating lipid metabolism. In addition, the pentadienoyl compound of the present application may increase a SIRT1 expression level in cells or SIRT1 activity, and thus may be used to prevent or treat a SIRT1-mediated disease. In addition, the pentadienoyl compound of the present application may reduce a CK2 expression level in cells or CK2 activity, and thus may be used to prevent or treat a CK2-mediated disease.

  本申请涉及一种新型的戊二烯酰化合物和包括该化合物的药物组合物。本申请的戊二烯酰化合物可用于通过抑制细胞内脂肪生成和脂质积累，激活脂质代谢，预防或治疗脂肪肝和脂肪肝相关疾病。此外，本申请的戊二烯酰化合物可能增加细胞中SIRT1的表达水平或SIRT1的活性，因此可用于预防或治疗SIRT1介导的疾病。此外，本申请的戊二烯酰化合物可能降低细胞中CK2的表达水平或CK2的活性，因此可用于预防或治疗CK2介导的疾病。
• [EN] (2E,4E)-5-PHENYL-PENTA-2,4-DIEN-1-ONE DERIVATIVE<br/>[FR] DÉRIVÉ DE (2E,4E)-5-PHÉNYL-PENTA-2,4-DIÈN-1-ONE<br/>[KO] (2E,4E)-5-페닐-펜타-2,4-다이엔-1-온 유도체
  申请人：BIOWAY INC

  公开号：WO2019190177A1

  公开（公告）日：2019-10-03

  본 출원은 신규한 펜타다이에오닐 화합물 및 이를 포함하는 약학적 조성물에 관한 것이다. 본 출원의 펜타다이에오닐 화합물은 세포 내 지방 형성 및 지방 축적을 억제하고 지방 대사를 활성화하여 지방간 및 지방간 관련 질환의 예방 또는 치료에 사용될 수 있다. 또한 본 출원의 펜타다이에오닐 화합물은 세포 내 SIRT1의 발현량을 증가시키거나 SIRT1의 활성을 증가시켜 SIRT1과 관련 있는 질환의 예방 또는 치료에 사용될 수 있다. 또한 본 출원의 펜타다이에오닐 화합물은 세포 내 CK2의 발현량을 감소시키거나 CK2의 활성을 감소시켜 CK2와 관련 있는 질환의 예방 또는 치료에 사용될 수 있다.