(2E,4E)-5-(3,4-dimethoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one | 66110-19-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E)-5-(3,4-dimethoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• 英文别名: (2E,4E)-5-(3,4-dimethoxyphenyl)-1-(piperidin-1-yl)penta-2,4-diene-1-one；(2E,4E)-5-(3,4-dimethoxyphenyl)-1-piperidin-1-ylpenta-2,4-dien-1-one
• CAS: 66110-19-8
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: GXGGAVLQUWJMBL-KBXRYBNXSA-N

物化性质

• 熔点：
  115 °C
• 沸点：
  506.0±38.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(3,4-dimethoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 以19%的产率得到(2E,4E)-5-(4-hydroxy-3-methoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
  参考文献：
  名称：

  设计，合成和鉴定抑制人5-LOX的新型香豆碱衍生物：抗氧化剂，假过氧化物酶和对接研究。

  摘要：

  5-Lipoxygenase（5-LOX）是参与促炎性白三烯生物合成的关键酶，可导致哮喘。开发有效的5-LOX抑制剂，特别是基于天然产物的抑制剂，具有很高的吸引力。香豆碱是白胡椒及其衍生物中的天然产物，在本文中被开发为5-LOX抑制剂。我们已经合成了二十四个衍生物，表征并评估了它们对5-LOX的抑制潜力。取代有多个羟基和多个甲氧基的香豆碱衍生物表现出最佳的5-LOX抑制作用。CP-209（一种邻苯二酚型二羟基衍生物）和CP-262-F2（一种邻位三羟基衍生物）在20 µM时分别显示出对5-LOX的抑制率为82.7％和82.5％。它们的IC50值分别为2.1±0.2 µM和2.3±0.2 µM，与齐留通相当，IC50 = 1.4±0.2 µM。CP-155，亚甲基二氧基衍生物（天然产物）和CP-194（2,4,6-三甲氧基衍生物）在20 µM时分别显示出对5-LOX的抑制率为76.0％和77

  DOI：

  10.1016/j.bmc.2018.12.043
• 作为产物：
  描述：

  1-(3,4-二甲氧基苯基)乙醇 在 氢氧化钾 、 氯化亚砜 、 sodium hydride 、 三氯氧磷 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (2E,4E)-5-(3,4-dimethoxyphenyl)-1-(piperidin-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

• Quorum Sensing and NF-κB Inhibition of Synthetic Coumaperine Derivatives from Piper nigrum
  作者：Yael Kadosh、Subramani Muthuraman、Karin Yaniv、Yifat Baruch、Jacob Gopas、Ariel Kushmaro、Rajendran Saravana Kumar

  DOI：10.3390/molecules26082293

  日期：——

  cellular factors, including the transcription Nuclear Factor kappa B (NF-κB); this factor is found to be upregulated in many inflammatory diseases, including those induced by bacterial infection. In this study, we tested 32 synthetic derivatives of coumaperine (CP), a known natural compound found in pepper (Piper nigrum), for Quorum Sensing Inhibition (QSI) and NF-κB inhibitory activities. Of the compounds

  称为群体感应（QS）的细菌通讯是减少毒力和治疗细菌感染的有希望的目标。感染会引起炎症，这一过程受许多细胞因子调节，包括转录核因子κB（NF-κB）；发现该因子在许多炎性疾病中被上调，包括细菌感染引起的那些。在这项研究中，我们测试了32种香豆素（CP）的合成衍生物，香豆素是一种在胡椒中发现的已知天然化合物（Piper nigrum），用于群体感应抑制（QSI）和NF-κB抑制活性。在测试的化合物中，发现有七个具有高QSI活性，三个抑制了细菌的生长，五个抑制了NF-κB。此外，某些CP化合物在一项以上的测试中具有活性。例如，化合物CP-286，CP-215和CP-158无细胞毒性，抑制NF-κB活化和QS，但不显示抗菌活性。CP-154抑制QS，降低NF-κB活化并抑制细菌生长。我们的结果表明，这些合成分子可能为进一步开发针对细菌感染的新型治疗剂提供基础。
• NOVEL PIPERINE DERIVATIVES AND USES THEREOF
  申请人：INDUSTRY-ACADEMIC COOPERATION FOUNDATION, YONSEI UNIVERSITY

  公开号：US20140371271A1

  公开（公告）日：2014-12-18

  The present invention provides novel piperine derivatives. The present pharmaceutical or food composition containing a piperine derivative as an active ingredient is very effective in preventing or treating metabolic diseases including obesity, diabetes, dyslipidemia, fatty liver and insulin resistance syndrome. Piperine derivatives of the present invention useful as pharmaceuticals compositions or functional food compositions has therapeutic efficacies for metabolic syndrome selected from the group consisting of obesity, diabetes, hyperlipidemia, fatty liver and insulin resistance syndrome, and also suppress the differentiation of progenitor cells and reduce the accumulation of triglycerides.

  本发明提供了新颖的胡椒碱衍生物。含有胡椒碱衍生物作为活性成分的药用或食品组合物对预防或治疗包括肥胖、糖尿病、血脂异常、脂肪肝和胰岛素抵抗综合征在内的代谢性疾病非常有效。本发明的胡椒碱衍生物作为药物组合物或功能性食品组合物具有治疗代谢综合征的疗效，包括肥胖、糖尿病、高血脂症、脂肪肝和胰岛素抵抗综合征，并且抑制前体细胞的分化并减少甘油三酯的积累。
• [EN] ANTI-QUORUM SENSING, ANTI-BIOFILM, AND INFLAMMATION ATTENUATING COMPOUNDS, COMPOSITIONS, AND METHODS OF USING SAME<br/>[FR] COMPOSÉS DE DÉTECTION ANTI-QUORUM, ANTI-BIOFILM, ET COMPOSÉS ATTÉNUANT L'INFLAMMATION, COMPOSITIONS ET LEURS MÉTHODES D'UTILISATION
  申请人：B G NEGEV TECHNOLOGIES AND APPLICATIONS LTD AT BEN GURION UNIV

  公开号：WO2022153306A1

  公开（公告）日：2022-07-21

  The present invention is directed to compounds having anti quorum sensing activity, anti-inflammatory activity or both, compositions comprising same, and methods of using same, such for treating a subject afflicted with a disease.

  本发明涉及具有抗群体感应活性、抗炎活性或两者的化合物，包括这些化合物的组合物以及使用它们的方法，例如用于治疗患有疾病的受试者。
• Composition and method for treating skin by administering silybin and piperine/terahydropiperine
  申请人：Cognis IP Management GmbH

  公开号：EP1902756A1

  公开（公告）日：2008-03-26

  Suggested are cosmetic compositions comprising in a cosmetically acceptable excipient (a) silybin and (b) piperine and/or tetrahydropiperine. The compositions are suitable for preventing and/or soothing dry skin or reactive skin against external stresses.

  建议的化妆品组合物含有化妆品可接受赋形剂 (a) 水飞蓟宾和 (b) 胡椒碱和/或四氢哌啶。这些复合物适用于预防和/或舒缓皮肤干燥或皮肤对外界压力的反应。
• Banerji, Avijit; Banerjee, Tapasri; Sengupta, Ratna, Journal of the Indian Chemical Society, 2002, vol. 79, # 11, p. 876 - 883
  作者：Banerji, Avijit、Banerjee, Tapasri、Sengupta, Ratna、Sengupta, Piyali、Das, Chittaranjan、Sahu, Anita

  DOI：——

  日期：——