(3E,5E)-3,5-bis(furan-2-ylmethylene)piperidin-4-one

• 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(furan-2-ylmethylene)piperidin-4-one
• 英文别名: (3E,5E)-3,5-bis(2-furylmethylene)piperidin-4-one；(3E,5E)-3,5-bis(furan-2-ylmethylidene)piperidin-4-one
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: SNOONVGPGGQOIR-MKICQXMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.4
• 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(furan-2-ylmethylene)piperidin-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以84%的产率得到(3E,5E)‐3,5‐bis(furan‐2‐ylmethylidene)piperidin‐4‐ol
  参考文献：
  名称：

  通过开发新型哌啶 4 取代亚胺来靶向 HIV-TB 合并感染：设计、合成、体外和计算机研究

  摘要：

  结核病是人类免疫缺陷 (HIV) 部门的“阿喀琉斯之踵”。HIV 阳性者感染结核病的可能性是其他人的 16-27 倍。但是抗逆转录病毒药物和抗结核药物之间的不良相互作用使得寻找一种单一的药物治疗方案来治疗 HIV-TB 合并感染是必要的。哌啶衍生物已被报道为抗 HIV 和抗结核药物。这启发了我们设计、合成和表征一系列 3,5-双（呋喃-2-基亚甲基）-哌啶-4-取代的亚胺（R1-R25），并进一步筛选了这些对结核分枝杆菌的体外抗结核活性H37Rv 和抗 HIV 活性。分子对接研究表明，与 EACP 还原酶 (1ZID.pdb) 和逆转录酶 (1REV.pdb) 靶标的结合相互作用非常有利。化合物 R7、R12、R17、R18、发现 R19、R20 作为抗结核药物比乙胺丁醇更有效（MIC 3.125 μg/ml）。与用作抗 HIV 药物的标准药物齐多夫定 (IC50 = 5.7 ± 0.04

  DOI：

  10.1002/ardp.201800358
• 作为产物：
  描述：

  糠醛 、 4-氧代哌啶酮盐酸盐 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以86%的产率得到(3E,5E)-3,5-bis(furan-2-ylmethylene)piperidin-4-one
  参考文献：
  名称：

  通过开发新型哌啶 4 取代亚胺来靶向 HIV-TB 合并感染：设计、合成、体外和计算机研究

  摘要：

  结核病是人类免疫缺陷 (HIV) 部门的“阿喀琉斯之踵”。HIV 阳性者感染结核病的可能性是其他人的 16-27 倍。但是抗逆转录病毒药物和抗结核药物之间的不良相互作用使得寻找一种单一的药物治疗方案来治疗 HIV-TB 合并感染是必要的。哌啶衍生物已被报道为抗 HIV 和抗结核药物。这启发了我们设计、合成和表征一系列 3,5-双（呋喃-2-基亚甲基）-哌啶-4-取代的亚胺（R1-R25），并进一步筛选了这些对结核分枝杆菌的体外抗结核活性H37Rv 和抗 HIV 活性。分子对接研究表明，与 EACP 还原酶 (1ZID.pdb) 和逆转录酶 (1REV.pdb) 靶标的结合相互作用非常有利。化合物 R7、R12、R17、R18、发现 R19、R20 作为抗结核药物比乙胺丁醇更有效（MIC 3.125 μg/ml）。与用作抗 HIV 药物的标准药物齐多夫定 (IC50 = 5.7 ± 0.04

  DOI：

  10.1002/ardp.201800358

文献信息

• Synthesis and Anticancer Evaluation of Bis Furfurylidene-4-piperidone Analog of 5-Fluorouracil
  作者：Rahul L. Jadhav、Pravin K. Pawar、Manisha V. Patil

  DOI：10.14233/ajchem.2017.20487

  日期：2017.4.30

  5-Fluorouracil (5-FU) displayed several side effects due to its nonspecific cytotoxicity for tumour cells. In order to overcome these disadvantages, numerous modifications of the 5-fluorouracil structure have been performed. In the present study, bis furfurylidene-4-piperidone substituted 5-flurouracil derivative is prepared and evaluated against various cancer cells. The resultant derivative is characterized by spectral data. This compound having 1,5-diaryl-3-oxo-1,4-pentadinenyl pharmacophore which interact with cellular thiols and produces cytotoxic activity whereas 5-flurouracil part showed anticancer activity by interacting with nucleic acid. The resulting synthesized compound has been screened for in vitro cytotoxic property by SRB assay method against breast and colon cancer cell lines. The results indicate that, this compound showed equipotent cytotoxicity against human breast cell lines as compared to standard, 5-flurouracil and doxorubicin. Acute toxicity was determined by OECD-423 guidelines. In vivo anticancer activity was evaluated in Swiss albino mice bearing Ehrlich Ascites Carcinoma (EAC). This compound showed significant anticancer activity against Ehrlich Ascites Carcinoma in Swiss albino mice. This study revealed the potentiality of this molecule for further development as anticancer agents.

  5-氟尿嘧啶 (5-FU) 由于其对肿瘤细胞的非特异性细胞毒性而表现出多种副作用。为了克服这些缺点，对5-氟尿嘧啶结构进行了多种修饰。在本研究中，制备了双糠基-4-哌啶酮取代的5-氟尿嘧啶衍生物，并针对各种癌细胞进行了评估。所得导数由光谱数据表征。该化合物具有1,5-二芳基-3-氧代-1,4-戊二烯基药效基团，可与细胞硫醇相互作用并产生细胞毒活性，而5-氟尿嘧啶部分通过与核酸相互作用而显示出抗癌活性。通过针对乳腺癌和结肠癌细胞系的 SRB 测定方法，筛选了所得合成化合物的体外细胞毒性特性。结果表明，与标准的 5-氟尿嘧啶和阿霉素相比，该化合物对人乳腺细胞系表现出同等的细胞毒性。急性毒性根据 OECD-423 指南确定。在患有艾利希腹水癌（EAC）的瑞士白化小鼠中评估了体内抗癌活性。该化合物对瑞士白化小鼠的艾利希腹水癌表现出显着的抗癌活性。这项研究揭示了该分子作为抗癌药物进一步开发的潜力。
• 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.