(2E,4E)-5-(4-methoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one | 66110-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2E,4E)-5-(4-methoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
• 英文别名: (2E,4E)-5-(4-methoxyphenyl)-1-piperidin-1-ylpenta-2,4-dien-1-one
• CAS: 66110-15-4
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: WKRSMNOYQVMCKF-FCXRPNKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 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：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-(4-methoxyphenyl)-1-(piperidin-1-yl)penta-2,4-dien-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Coumaperine
  参考文献：
  名称：

  一种胡椒碱衍生物及其制备方法和用途

  摘要：

  本发明提供了一种胡椒碱衍生物及其制备方法和用途。该胡椒碱衍生物为式(I)所示的化合物、或其盐、或其立体异构体、或其水合物。本发明化合物能够有效保护神经细胞，提高神经细胞的存活率，因此，本发明化合物可以有效治疗神经退行性疾病，可以用于制备治疗神经退行性疾病的药物。

  公开号：

  CN111072597B
• 作为产物：
  描述：

  (2E,4E)-ethyl 5-(4'-methoxyphenyl)penta-2,4-dienoate 在 氢氧化钾 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 (2E,4E)-5-(4-methoxyphenyl)-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

• Design, synthesis and identification of novel coumaperine derivatives for inhibition of human 5-LOX: Antioxidant, pseudoperoxidase and docking studies
  作者：Subramani Muthuraman、Shweta Sinha、C.S. Vasavi、Kamran Manzoor Waidha、Biswarup Basu、Punnagai Munussami、M.M. Balamurali、Mukesh Doble、Rajendran Saravana Kumar

  DOI：10.1016/j.bmc.2018.12.043

  日期：2019.2

  Developing potent 5-LOX inhibitors especially, natural product based ones, are highly attractive. Coumaperine, a natural product found in white pepper and its derivatives were herein developed as 5-LOX inhibitors. We have synthesized twenty four derivatives, characterized and evaluated their 5-LOX inhibition potential. Coumaperine derivatives substituted with multiple hydroxy and multiple methoxy groups

  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
• 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。
• A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues
  作者：Adriano Bauer、Jun-Hyun Nam、Nuno Maulide

  DOI：10.1055/s-0037-1611652

  日期：2019.3

  A quantitative synthesis of piperine from commercially available starting material is presented. The synthesis relies on a stereoselective nucleophilic attack of an in situ generated cuprate onto a cyclobutene lactone. The so-formed aryl-substituted cyclobutene spontaneously undergoes a conrotatory 4π-electrocyclic ring opening to form the 4-aryl pentadienoic acid as a single diastereoisomer. The high-yielding

  介绍了从市售原料中定量合成胡椒碱的方法。该合成依赖于原位生成的铜酸盐对环丁烯内酯的立体选择性亲核攻击。如此形成的芳基取代的环丁烯自发地进行旋转 4π-电环开环以形成 4-芳基戊二烯酸作为单一非对映异构体。高产合成可以很容易地在芳基和酰胺部分上进行调节，以合成各种胡椒碱类似物。
• 一种胡椒碱衍生物及其制备方法和用途
  申请人：四川大学

  公开号：CN111072597B

  公开（公告）日：2022-12-09

  本发明提供了一种胡椒碱衍生物及其制备方法和用途。该胡椒碱衍生物为式(I)所示的化合物、或其盐、或其立体异构体、或其水合物。本发明化合物能够有效保护神经细胞，提高神经细胞的存活率，因此，本发明化合物可以有效治疗神经退行性疾病，可以用于制备治疗神经退行性疾病的药物。
• (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。