胡椒基戊二烯酸钾 | 161196-20-9

• 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
• 中文名称: 胡椒基戊二烯酸钾
• 英文名称: potassium piperate
• 英文别名: potassium;(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoate
• CAS: 161196-20-9
• 化学式: C₁₂H₉O₄*K
• 分子量: 256.299
• InChiKey: OTCXSDBBPSOWHQ-LMFJUDGVSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.26
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  胡椒基戊二烯酸钾 在 硫酸 作用下， 以 水 为溶剂， 生成 5-(3,4-亚甲基二氧苯基)-2,4-戊二烯酸
  参考文献：
  名称：

  [EN] Sodium Piperonyl Pentadienoate and Use of the Same for Lowering Blood Lipid
  [FR] PIPÉRONYLPENTADIÉNOATE DE SODIUM ET SON UTILISATION POUR LA RÉDUCTION DES LIPIDES SANGUINS

  摘要：

  本发明公开了戊二烯基苯甲酸钠，以及含有戊二烯基苯甲酸钠的药物组合物或保健品，以及戊二烯基苯甲酸钠的制备方法，以及将戊二烯基苯甲酸钠用于降低血脂的用途，包括在制备降低血清总胆固醇、降低低密度脂蛋白胆固醇、降低甘油三酯以及防止高密度脂蛋白胆固醇降低的药物或保健品中使用戊二烯基苯甲酸钠。

  公开号：

  WO2013078983A1
• 作为产物：
  描述：

  胡椒碱 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以5 g的产率得到胡椒基戊二烯酸钾
  参考文献：
  名称：

  新胡椒碱衍生物的合成，光谱表征，DFT计算和初步抗真菌活性

  摘要：

  合成了四种新的胡椒碱衍生物PC1-PC4，并通过红外（IR）以及H和C核磁共振（NMR）光谱对它们的结构进行了全面表征。使用B3LYP-D3 / 6-31G（d，p）和6-311 + G（2d，p）基组使用密度泛函理论（DFT）进行量子化学计算。电子性能，例如最高占据分子轨道（HOMO）与最低未占据分子轨道（LUMO）之间的能隙以及一些全局化学反应性描述子，被用来研究化合物的反应性和稳定性。通过使用轨距不变原子轨道（GIAO）方法计算H和C NMR化学位移，并将其与实验值进行比较。此外，还针对抗念珠菌，毛癣菌和小孢子菌的菌株进行了抗真菌研究，对这些化合物进行了评估，

  DOI：

  10.21577/0103-5053.20200203

文献信息

• Novel Strobilurin Derivatives Containing Carboxylate Unit as Potential Antifungal Agents
  作者：Longzhu Bao、Shuangshuang Wang、Di Song、Jingjing Wang、Xiali Yue、Xiufang Cao

  DOI：10.2174/1570180816666190325164452

  日期：2020.3.27

  all fungi. Further fungicidal activity studies indicate that some of these novel strobilurin derivatives containing carboxylate unit exhibited potential in vitro fungicidal activities at the dosage of 6.25 mg/L-1. Conclusion: A series of the ortho-substituted benzyl carboxylates derivatives containing β- methoxyacrylate moiety were designed and synthesized by modifying the side chain of traditional strobilurin

  背景：由于单一杀真菌剂广泛用于控制农作物疾病，抗药性个体的增加导致控制失败。寻找具有杀真菌活性的分子仍在进行中。鬼臼苦素是在农业化学领域中最广泛使用的杀真菌剂之一。已经开发出许多具有高活性和低毒性的嗜球果伞素衍生物。 方法：在本研究中，通过（E）-甲基2-（2-（溴-乙基）苯基）-2-甲氧基-亚氨基乙a与各种羧酸的反应有效地合成了一系列新型的邻位取代的苄基羧酸盐。通过1 H NMR，13 C NMR和ESI-MS分析确认并表征了它们的结构。根据用于实验室生物活性测试的农药指南，筛选了它们对六种主要经济作物的常见植物病原真菌的杀真菌活性。 结果：主要杀真菌活性测试结果表明，所有化合物均以100 ppm的浓度对Compd和13种植物病原真菌的生长具有一定的抑制作用。3对所有真菌的抑制作用最明显。进一步的杀真菌活性研究表明，其中一些含有羧酸酯单元的新型伞形龙蛋白衍生物在剂量为6.25 mg / L-1时具有潜在的体外杀真菌活性。
• 一种药用化合物胡椒酸己二胺及其制备工艺
  申请人：吐尔孙拜克·叶尔达

  公开号：CN105348250A

  公开（公告）日：2016-02-24

  本发明公开了一种药用化合物胡椒酸己二胺及其制备工艺。胡椒酸己二胺化学结构式如下所示：工艺步骤：(1)胡椒酸钾的制备；(2)胡椒酸的制备；(3)胡椒酸乙酯的制备；(4)胡椒酸己二胺的制备。优点：一是胡椒酸己二胺，是降血脂作用显著的半天然化合物，是一种新合成的化合物。通过小白鼠给药试验，证实对高血脂症动物血清总胆固醇、甘油三脂和低密度脂蛋白都具有显著降低作用，急毒和细胞实验中没有发现任何毒性反应。二是胡椒酸己二胺，如果替代他汀类药，只要占有国际市场1/10份额，每年可创收20-50亿美元，经济效益巨大。三是国内外还没有发现胡椒酸己二胺的合成工艺和生产技术，这是一项开拓性的创新。
• New Diesters Derived from Piperine: in silico Study and Evaluation of Their Antimicrobial Potential
  作者：Emmely Trindade、Helivaldo Souza、Maria Cláudia Brandão、Hermes Neto、Edeltrudes Lima、Bruno Lira、Petrônio de Athayde-Filho、José Barbosa-Filho

  DOI：10.21577/0103-5053.20200053

  日期：——

  Piperine, previously extracted from black pepper (Piper nigrum L.), was used as a precursor for the synthesis of twelve new diester derivatives. The final products were obtained through the bimolecular nucleophilic substitution reaction (S(N)2) of the alkyl 2-chloroacetates and the salt of piperic acid, obtained from the basic hydrolysis of piperine. The compounds were synthesized with yields of 55-84% and characterized by infrared spectroscopy and H-1 and C-13 nuclear magnetic resonance. The evaluation of the compounds' potential as new drug candidates was done through an in silico study of ADME properties (absorption, distribution, metabolization and excretion) and evaluation of antimicrobial activity against bacterial strains (Staphylococcus aureus and Pseudmuonas aeruginosa). yeasts (Candida albicans and Candida tropicalis) and filamentous fungi (Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger). The in silico study showed that the compounds were good drug candidates and antimicrobial evaluation demonstrated that 9 of the 12 compounds exhibited a minimum inhibitory concentration (MIC) ranging 1024-256 mu g mL(-1).
• Synthesis, in silico Study and Antimicrobial Activity of New Piperine Derivatives Containing Substituted δ-Esters
  作者：Emmely Trindade、Thalisson Dutra、Maria Brandão、Hermes Diniz Neto、Edeltrudes Lima、Bruno Lira、Petrônio de Athayde-Filho、José Barbosa-Filho

  DOI：10.21577/0103-5053.20200140

  日期：——
• A novel piperine analogue exerts in vivo antitumor effect by inducing oxidative, antiangiogenic and immunomodulatory actions
  作者：Rafael Carlos Ferreira、Tatianne Mota Batista、Sâmia Sousa Duarte、Daiana Karla Frade Silva、Thaís Mangeon Honorato Lisboa、Raquel Fragoso Pereira Cavalcanti、Fagner Carvalho Leite、Vivianne Mendes Mangueira、Tatyanna Kélvia Gomes de Sousa、Renata Albuquerque de Abrantes、Emmely Oliveira da Trindade、Petrônio Filgueiras de Athayde-Filho、Maria Cláudia Rodrigues Brandão、Karina Carla de Paula Medeiros、Davi Felipe Farias、Marianna Vieira Sobral

  DOI：10.1016/j.biopha.2020.110247

  日期：2020.8

  Structural diversity characterizes natural products as prototypes for design of lead compounds. The aim of this study was to synthetize, and to evaluate the toxicity and antitumor action of a new piperine analogue, the butyl 4-(4-nitrobenzoate)-piperinoate (DE-07). Toxicity was evaluated against zebrafish, and in mice (acute and micronucleus assays). To evaluate the DE-07 antitumor activity Ehrlich ascites carcinoma model was used in mice. Angiogenesis, Reactive Oxygen Species (ROS) production and cytokines levels were investigated. Ninety-six hours exposure to DE-07 did not cause morphological or developmental changes in zebrafish embryos and larvae, with estimated LC50 (lethal concentration 50%) higher than 100 mu g/mL. On the acute toxicity assay in mice, LD50 (lethal dose 50%) was estimated at around 1000 mg/kg, intraperitoneally (i.p.). DE-07 (300 mg/kg, i.p.) did not induce increase in the number of micronucleated erythrocytes in mice, suggesting no genotoxicity. On Ehrlich tumor model, DE-07 (12.5, 25 or 50 mg/kg, i.p.) induced a significant decrease on cell viability. In addition, there was an increase on ROS production and a decrease in peritumoral microvessels density. Moreover, DE-07 induced an increase of cytokines levels involved in oxidative stress and antiangiogenic effect (IL-1 beta, TNF-alpha and IL-4). No significant clinical toxicological effects were recorded in Ehrlich tumor transplanted animals. These data provide evidence that DE-07 presents low toxicity, and antitumor effect via oxidative and antiangiogenic actions by inducing modulation of inflammatory response in the tumor microenvironment.