(3E,5E)-3,5-dibenzylidene-1-tetradecanoylpiperidin-4-one | 1340541-58-3

• 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-dibenzylidene-1-tetradecanoylpiperidin-4-one
• 英文别名: 3,5-bis(benzylidene)-1-tetradecanoyl-4-piperidone
• CAS: 1340541-58-3
• 化学式: C₃₃H₄₃NO₂
• 分子量: 485.71
• InChiKey: RNWSWTBHMCZUSD-AMLXCYGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  肉豆蔻酸 在 氯化亚砜 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 (3E,5E)-3,5-dibenzylidene-1-tetradecanoylpiperidin-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

• Bis[3,5-bis(benzylidene)-4-oxo-1-piperidinyl]amides: A Novel Class of Potent Cytotoxins
  作者：Swagatika Das、Umashankar Das、Armando Varela-Ramírez、Carolina Lema、Renato J. Aguilera、Jan Balzarini、Erik De Clercq、Stephen G. Dimmock、Dennis K. J. Gorecki、Jonathan R. Dimmock

  DOI：10.1002/cmdc.201100199

  日期：2011.10.4

  candidate cytotoxins increases potency more than two‐fold. This concept was verified in one‐third of our comparisons using human Molt 4/C8 and CEM T‐lymphocytes and murine L1210 cells. In addition, the significant potencies of various members of our compound series justified further studies. Molecular modeling revealed that relative locations of the amidic groups correlate with cytotoxicity. A potent cytotoxic

  本研究的主要目的是检验细胞毒性协同作用的理论。在这项探索性研究中，我们检验了以下假设：将一系列候选细胞毒素中可用于硫醇烷基化的位点数量增加一倍，可使效力增加两倍以上。这一概念在我们使用人 Molt 4/C8 和 CEM T 淋巴细胞和鼠 L1210 细胞的三分之一比较中得到了验证。此外，我们的化合物系列中各种成员的显着效力证明了进一步研究是合理的。分子模型显示酰胺基团的相对位置与细胞毒性相关。一种有效的细胞毒性化合物，1,2-双（3,5-二亚苄基-4-氧代-哌啶-1-基）乙烷-1,2-二酮（1a) 抑制了大量人类肿瘤细胞系的生长，并且对某些非粘附细胞表现出比对粘附肿瘤或成纤维细胞更大的毒性。1a的作用方式包括诱导细胞凋亡和坏死。
• 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.