(3E,5E)-3,5-bis(pyridin-2-ylmethylene)piperidin-4-one | 342808-24-6

• 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: (3E,5E)-3,5-bis(pyridin-2-ylmethylene)piperidin-4-one
• 英文别名: UBS 186；3,5-Bis(2-pyridylmethylene)piperidine-4-one；(3E,5E)-3,5-bis(pyridin-2-ylmethylidene)piperidin-4-one
• CAS: 342808-24-6
• 化学式: C₁₇H₁₅N₃O
• 分子量: 277.326
• InChiKey: GXFKPANENAOEOK-UTLPMFLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E,5E)-3,5-bis(pyridin-2-ylmethylene)piperidin-4-one 、 棕榈酰氯 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 17.0h， 以53%的产率得到(3E,5E)-1-palmitoyl-3,5-bis(pyridin-2-ylmethylene)piperidin-4-one
  参考文献：
  名称：

  Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors

  摘要：

  A series of five 3,5-bisarylidene-4-piperidones designed as analogs of curcumin and their twenty five fatty acid conjugates were synthesized as candidate anticancer agents. The fatty acid conjugates were designed for efficient delivery of these compounds at the targeted cancer sites. The cytostatic potential of these compounds was evaluated against three representative cancer cell lines namely murine leukemic L1210 cells, and human T-lymphocyte CEM cells and cervical HeLa cells. Most compounds were found to exhibit significant anti-cancer activity in vitro. QSAR studies indicated electrophilicity of these compounds towards cellular nucleophiles may have a key role to play in their cytostatic activity. Representative compounds were also tested for topoisomerase II alpha inhibitory potential, which indicated strong catalytic inhibition of the enzyme in vitro. The data showed that the fatty acid conjugates also possessed robust antioxidant activity in multiple analyses. This study also indicated that these compounds prompted significantly lower cellular damage in human fibroblasts than a currently used cancer drug sorafenib in vitro. The wide spectrum of anticancer action, supplemented with antioxidant potential along with non-toxic manifestations, certainly augment the anticancer candidacy of the novel fatty acid conjugates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.042
• 作为产物：
  描述：

  吡啶-2-甲醛 、 4-氧代哌啶酮盐酸盐 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以77%的产率得到(3E,5E)-3,5-bis(pyridin-2-ylmethylene)piperidin-4-one
  参考文献：
  名称：

  Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors

  摘要：

  A series of five 3,5-bisarylidene-4-piperidones designed as analogs of curcumin and their twenty five fatty acid conjugates were synthesized as candidate anticancer agents. The fatty acid conjugates were designed for efficient delivery of these compounds at the targeted cancer sites. The cytostatic potential of these compounds was evaluated against three representative cancer cell lines namely murine leukemic L1210 cells, and human T-lymphocyte CEM cells and cervical HeLa cells. Most compounds were found to exhibit significant anti-cancer activity in vitro. QSAR studies indicated electrophilicity of these compounds towards cellular nucleophiles may have a key role to play in their cytostatic activity. Representative compounds were also tested for topoisomerase II alpha inhibitory potential, which indicated strong catalytic inhibition of the enzyme in vitro. The data showed that the fatty acid conjugates also possessed robust antioxidant activity in multiple analyses. This study also indicated that these compounds prompted significantly lower cellular damage in human fibroblasts than a currently used cancer drug sorafenib in vitro. The wide spectrum of anticancer action, supplemented with antioxidant potential along with non-toxic manifestations, certainly augment the anticancer candidacy of the novel fatty acid conjugates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.12.042

文献信息

• CURCUMIN ANALOGS WITH ANTI-TUMOR AND ANTI-ANGIOGENIC PROPERTIES
  申请人：Snyder James P.

  公开号：US20080234320A1

  公开（公告）日：2008-09-25

  The present invention is directed to curcumin analogs exhibiting anti-tumor and anti-angiogenic properties, pharmaceutical formulations including such compounds and methods of using such compounds.

  本发明涉及展现抗肿瘤和抗血管生成特性的姜黄素类似物，包括这些化合物的制药配方和使用这些化合物的方法。
• US7371766B2
  申请人：——

  公开号：US7371766B2

  公开（公告）日：2008-05-13
• US7842705B2
  申请人：——

  公开号：US7842705B2

  公开（公告）日：2010-11-30
• [EN] COMBINATION THERAPIES FOR TREATMENT OF CANCER AND INFLAMMATORY DISEASES<br/>[FR] THÉRAPIES COMBINÉES POUR LE TRAITEMENT DU CANCER ET DES MALADIES INFLAMMATOIRES
  申请人：UNIV EMORY

  公开号：WO2008150899A1

  公开（公告）日：2008-12-11

  [EN] The present invention is directed to combinations of compounds useful in the treatment and prevention of cancer and inflammatory conditions or diseases. In particular embodiments, the combinations comprise one or more compounds that are NF-?B inhibitors or p38 MAPK inhibitors. The invention further provides pharmaceutical compositions and methods of treatment using the combinations. In one embodiment, the NF -KB inhibitor is a curcumin analog.
  [FR] La présente invention concerne des combinaisons de composés utiles dans le traitement et la prévention du cancer et d'affections ou de maladies inflammatoires. Dans des modes de réalisation particuliers, les combinaisons comprennent un ou plusieurs composés qui sont des inhibiteurs de NF-KB ou des inhibiteurs de p38 MAPK. L'invention concerne en outre des compositions pharmaceutiques et des procédés de traitement utilisant les combinaisons. Dans un mode de réalisation, l'inhibiteur de NF-KB est un analogue de curcumine.
• Investigation of fatty acid conjugates of 3,5-bisarylmethylene-4-piperidone derivatives as antitumor agents and human topoisomerase-IIα inhibitors
  作者：Elizabeth Potter、Mamta Jha、Khushwant S. Bhullar、H.P. Vasantha Rupasinghe、Jan Balzarini、Amitabh Jha

  DOI：10.1016/j.bmc.2014.12.042

  日期：2015.2

  A series of five 3,5-bisarylidene-4-piperidones designed as analogs of curcumin and their twenty five fatty acid conjugates were synthesized as candidate anticancer agents. The fatty acid conjugates were designed for efficient delivery of these compounds at the targeted cancer sites. The cytostatic potential of these compounds was evaluated against three representative cancer cell lines namely murine leukemic L1210 cells, and human T-lymphocyte CEM cells and cervical HeLa cells. Most compounds were found to exhibit significant anti-cancer activity in vitro. QSAR studies indicated electrophilicity of these compounds towards cellular nucleophiles may have a key role to play in their cytostatic activity. Representative compounds were also tested for topoisomerase II alpha inhibitory potential, which indicated strong catalytic inhibition of the enzyme in vitro. The data showed that the fatty acid conjugates also possessed robust antioxidant activity in multiple analyses. This study also indicated that these compounds prompted significantly lower cellular damage in human fibroblasts than a currently used cancer drug sorafenib in vitro. The wide spectrum of anticancer action, supplemented with antioxidant potential along with non-toxic manifestations, certainly augment the anticancer candidacy of the novel fatty acid conjugates. (C) 2014 Elsevier Ltd. All rights reserved.