1-[1-oxo-3-(3,4-methylenedioxyphenyl)-2E-propenyl]-pyrrolidine | 74957-52-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-[1-oxo-3-(3,4-methylenedioxyphenyl)-2E-propenyl]-pyrrolidine
• 英文别名: (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(pyrrolidin-1-yl)prop-2-en-1-one；3-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)-(2E)-2-propen-1-one；tortodofuorpyramide；1-(3-(1,3-Benzodioxol-5-yl)-1-oxo-2-propenyl)pyrrolidine；(E)-3-(1,3-benzodioxol-5-yl)-1-pyrrolidin-1-ylprop-2-en-1-one
• CAS: 74957-52-1
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: SXFYVDPKNPGHKJ-GQCTYLIASA-N

物化性质

• 沸点：
  447.1±40.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,4-methylenedioxy-trans-cinnamic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-[1-oxo-3-(3,4-methylenedioxyphenyl)-2E-propenyl]-pyrrolidine
  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

• Treatment of skin conditions
  申请人：BTG International Limited

  公开号：US20020168369A1

  公开（公告）日：2002-11-14

  The present invention provides piperine and analogues or derivatives thereof for the treatment of skin conditions treatable by stimulation of melanocyte proliferation, such as vitiligo, and also for treating skin cancer. The piperine and analogues or derivatives thereof may also be used to cosmetically promote or enhance the natural coloration of the skin.

  本发明提供了辣椒碱及其类似物或衍生物，用于治疗可通过刺激黑色素细胞增殖来治疗的皮肤状况，如白癜风，并且用于治疗皮肤癌。辣椒碱及其类似物或衍生物也可用于美容促进或增强皮肤的自然着色。
• Structure–Activity Relationship of Piplartine and Synthetic Analogues against Schistosoma mansoni and Cytotoxicity to Mammalian Cells
  作者：Yuri Campelo、Alicia Ombredane、Andreanne Vasconcelos、Lucas Albuquerque、Daniel Moreira、Alexandra Plácido、Jefferson Rocha、Harold Hilarion Fokoue、Lydia Yamaguchi、Ana Mafud、Yvonne Mascarenhas、Cristina Delerue-Matos、Tatiana Borges、Graziella Joanitti、Daniel Arcanjo、Massuo Kato、Selma Kuckelhaus、Marcos Silva、Josué Moraes、José Leite

  DOI：10.3390/ijms19061802

  日期：——

  1M, 14B and 6B) against Schistosoma mansoni adult worms, as well as its cytotoxicity to mammalian cells using murine fibroblast (NIH-3T3) and BALB/cN macrophage (J774A.1) cell lines. In addition, density functional theory calculations and in silico analysis were used to predict physicochemical and toxicity parameters. Bioassays revealed that piplartine is active against S. mansoni at low concentrations

  血吸虫病是由血吸虫属的蠕虫扁虫引起的，是一种主要与贫困相关的传染病，影响了全世界数百万人。由于该疾病的治疗仅依赖于吡喹酮的使用，因此迫切需要鉴定新的抗血吸虫病药物。Piplartine是一种酰胺生物碱，存在于几种Piper物种（Piperaceae）中，具有抗血吸虫病的特性。这项研究的目的是评估piplartine及其五种合成类似物（19A，1G，1M，14B和6B）对曼氏血吸虫成虫的结构-功能关系，以及使用鼠成纤维细胞（NIH）对哺乳动物细胞的细胞毒性-3T3）和BALB / cN巨噬细胞（J774A.1）细胞系。此外，密度泛函理论计算和计算机分析用于预测理化和毒性参数。生物测定表明，吡普拉汀在低浓度（5×10 µM）下对曼氏链球菌有活性，但其类似物却没有。相比之下，基于3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑溴化物（MTT）和流式细胞术测定，吡普拉汀在785 µM的哺乳动
• Rapid access to cinnamamides and piper amides <i>via</i> three component coupling of arylaldehydes, amines, and Meldrum's acid
  作者：Santanu Ghosh、Chandan K. Jana

  DOI：10.1039/c9gc02937k

  日期：——

  A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation

  已经报道了通过概念上新颖的醛，胺和梅德鲁姆酸的三组分反应合成肉桂酰胺和哌啶酰胺的实用方法。该反应在操作简单的条件下进行，无需借助偶联剂，氧化剂或催化剂，而偶联剂，氧化剂或催化剂是通过已知方法制备肉桂酰胺/哌酰胺所必需的。避免了通常由于使用偶联剂，氧化剂或催化剂而产生的不希望有的化学废物，从而使该反应更经济。
• Use of piperine and derivatives thereof for the therapy of neurological conditions
  申请人：Sygnis Bioscience GmbH & Co. KG

  公开号：EP2011495A1

  公开（公告）日：2009-01-07

  The present invention relates to the use of piperine and derivatives thereof for the preparation of a pharmaceutical composition for treating and/or preventing a neuronal condition where there is a need of neuroprotection and/or neuroregeneration. The invention furthermore relates to the use of piperine and derivatives thereof for the in vitro differentiation of neuronal stem cells and the use of such pre-treated cells for stem cell therapy von neurological conditions.

  本发明涉及使用胡椒碱及其衍生物制备药物组合物，用于治疗和/或预防需要神经保护和/或神经再生的神经元疾病。本发明还涉及将胡椒碱及其衍生物用于神经元干细胞的体外分化，以及将这种预处理细胞用于干细胞治疗神经系统疾病。
• Effects of piperine analogues on stimulation of melanocyte proliferation and melanocyte differentiation
  作者：Radhakrishnan Venkatasamy、Laura Faas、Antony R Young、Amala Raman、Robert C Hider

  DOI：10.1016/j.bmc.2004.01.036

  日期：2004.4

  A wide range of piperine analogues has been synthesised in order to undertake a structure-activity study of their ability to stimulate melanocyte proliferation. Results demonstrate that an aromatic ring containing at least one ether function and a carbonyl group containing side chain is essential for this activity. A number of highly active piperine analogues have been identified, for instance 1-(3,4-methylenedioxyphenyl)-penta-2E,4E-dienoic acid methyl ester (3a), 1-E,E-piperinoyl-isobutylamine (4f) and 1-(3,4-methylenedioxyphenyl)-pentanoic acid cyclohexyl amide (20). A selection of analogues has also been evaluated for their effect on melanocyte morphology and melanogenesis. The piperine analogues altered cell morphology by increasing dendrite formation leading to bi-, tri- and quadripolar cells. These same analogues were found to increase total melanin in cell cultures, although melanin content per cell was not significantly altered from control in the presence of these compounds. (C) 2004 Elsevier Ltd. All rights reserved.