Piperettine | 583-34-6

• 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: Piperettine
• 英文别名: (2E,4E,6E)-7-(benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)hepta-2,4,6-trien-1-one；1-[1-oxo-7-(3,4-methylenedioxyphenyl)-2E,4E,6E-heptatrienyl]-piperidine；piperettin；pipertine；(2E,4E,6E)-7-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylhepta-2,4,6-trien-1-one
• CAS: 583-34-6
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: DLKOUKNODPCIHZ-UMYWTXKFSA-N

物化性质

• 沸点：
  531.1±45.0 °C(Predicted)
• 密度：
  1.188±0.06 g/cm3(Predicted)
• 熔点：
  146-149 °C
• 物理描述：
  Solid
• 保留指数：
  3272.9;3209

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  Piperettine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 7-(1,3-Benzodioxol-5-yl)-1-piperidin-1-ylheptan-1-one
  参考文献：
  名称：

  Adesina; Adebayo; Adesina, Pharmazie, 2002, vol. 57, # 9, p. 622 - 627

  摘要：

  DOI：
• 作为产物：
  描述：

  山梨酸 在 氯化亚砜 、 potassium tert-butylate 、 三乙胺 作用下， 以 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 13.0h， 生成 Piperettine
  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

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。
• Stereoselective synthesis of naturally occurring unsaturated amide alkaloids by a modified Ramberg–Bäcklund reaction
  作者：Yang Li、Yu Zhang、Zhi Huang、Xiaoping Cao、Kun Gao

  DOI：10.1139/v04-028

  日期：2004.5.1

  A convenient and rapid approach for the synthesis of naturally occurring unsaturated amide alkaloids 1a–1n by the recently developed one-flask Ramberg–Backlund reaction is described. The starting material was alcohol 3, which was transformed into thiolacetate 4 using the Mitsunobu reaction. In situ cleavage of acetyl moiety of 4, followed by alkylation of the resulting thiol with appropriate chloroacetamide

  描述了一种通过最近开发的单瓶 Ramberg??Backlund 反应合成天然存在的不饱和酰胺生物碱 1a??1n 的方便快捷的方法。起始原料是醇 3，使用 Mitsunobu 反应将其转化为硫代乙酸酯 4。4 的乙酰基部分的原位裂解，然后用合适的氯乙酰胺 5 将所得硫醇烷基化，提供硫化物 6。硫化物 6 氧化得到相应的砜 2。在氧化铝-存在下用二溴二氟甲烷处理砜 2二氯甲烷溶液中负载的氢氧化钾得到不饱和酰胺生物碱1a??1n。据我们所知，1e和1i的合成是首次报道。关键词：合成，不饱和酰胺生物碱，Ramberg??Backlund反应。
• [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。
• Dehmlow, Eckehard V.; Shamout, Abdul Rahman, Journal of Chemical Research, Miniprint, 1981, # 4, p. 1178 - 1184
  作者：Dehmlow, Eckehard V.、Shamout, Abdul Rahman

  DOI：——

  日期：——
• Synthesis of coumaperine derivatives: Their NF-κB inhibitory effect, inhibition of cell migration and their cytotoxic activity
  作者：Natarajan Nandakumar、Subramani Muthuraman、Pushparathinam Gopinath、Pattusamy Nithya、Jacob Gopas、Rajendran Saravana Kumar

  DOI：10.1016/j.ejmech.2016.10.047

  日期：2017.1

  Coumaperine (an amide alkaloid, present in white piper) and its derivatives were synthesized and investigated for their cytotoxicity against L428 and A549 cells and their NF-kappa B inhibitory activity. It was found that the coumaperine derivatives CP-9 and CP-38 suppress NF-kappa B subunits p50 and p65 in nuclear fractions by western blot and by NF-kappa B luciferase reporter gene assay in a dose dependent manner. Confirmation of these results was obtained by confocal microscopy. CP-9, CP-32 and CP-38 also exhibited dose dependent cell cytotoxicity in a L428 cells expressing constitutively active NF-kappa B and in A549 cells, with an IC50 value of 43.25 0.39 mu g/ml and 16.85 mu g/ml respectively against L428 cells and 57.15 mu g/ml, 69.1 mu g/ml and 63.2 mu g/ml respectively against A549 cells. In addition, the coumaperine derivatives show remarkable inhibitory activity on the cancer cell migration assay against A549 lung adenocarcinoma cells at the concentrations of 5 mu g/ml, 10 mu g/ml, and 5 mu g/ml of CP-9, CP-32 and CP-38 respectively. Aromatic substituents and number of olefinic double bond in coumaperine derivatives found to influence the inhibitory activity. In luciferase reporter gene assay, di-olefin conjugated coumaperine derivatives, CP-38, CP-32 and PIP exhibited higher inhibitory activity than their corresponding tri-olefin conjugated coumaperine derivatives, CP-102, CP-146 and PIP-155 respectively. CP-32 with a stronger electron donating group (-N(CH3)(2)) showed better inhibitory activity in luciferase reporter gene assay and in cell proliferation of L428 cells. Simple coumaperine derivative (CP-9, with no substituent) effectively inhibited A549 cells proliferation and migration than the other coumaperine derivatives. CP-9 and CP-38 diminish significantly the NF-kappa B subunits (p50 and p65) of L428 cells in nuclear fractions at the dosage of 10 mu g/ml and 30 mu g/ml respectively. Which clearly shows that CP-9 and CP-38 inactivate the NF-kappa B pathway in vitro. (C) 2016 Elsevier Masson SAS. All rights reserved.