3,5-bis(thiophen-2-ylmethylene)-piperidin-4-one | 937738-62-0

• 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: 3,5-bis(thiophen-2-ylmethylene)-piperidin-4-one
• 英文别名: 3,5-bis(thiophen-2-ylmethylidene)piperidin-4-one
• CAS: 937738-62-0
• 化学式: C₁₅H₁₃NOS₂
• 分子量: 287.406
• InChiKey: HAMFEFSJOFWARR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  85.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-bis(thiophen-2-ylmethylene)-piperidin-4-one 、 对甲氧基苯异氰酸酯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以84%的产率得到(3E,5E)-N-(4-methoxyphenyl)-4-oxo-3,5-bis(thiophen-2-ylmethylene)piperidine-1-carboxamide
  参考文献：
  名称：

  Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics

  摘要：

  吡啶甲酰胺（姜黄素类似物）显示出对HCT116（结肠）、MCF7（乳腺）和A431（鳞状皮肤）癌细胞系有很好的抗增殖特性，其效力高于5-氟尿嘧啶。

  DOI：

  10.1039/c9ra05661k
• 作为产物：
  描述：

  2-噻吩甲醛 、 4-哌啶酮 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 3,5-bis(thiophen-2-ylmethylene)-piperidin-4-one
  参考文献：
  名称：

  Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics

  摘要：

  吡啶甲酰胺（姜黄素类似物）显示出对HCT116（结肠）、MCF7（乳腺）和A431（鳞状皮肤）癌细胞系有很好的抗增殖特性，其效力高于5-氟尿嘧啶。

  DOI：

  10.1039/c9ra05661k

文献信息

• Design, synthesis, and biological evaluation of novel <strong>EF24 </strong>and <strong>EF31 </strong>analogs as potential IκB kinase β inhibitors for the treatment of pancreatic cancer
  作者：Xuemeng Xie、Jinfu Tu、Heyi You、Bingren Hu

  DOI：10.2147/dddt.s133172

  日期：——

  Given the important role that inhibitory kappa B (IκB) kinase β (IKKβ) plays in pancreatic cancer (PC) development and progression, inhibitors targeting IKKβ are believed to be increasingly popular as novel anti-PC therapies. Two synthetic molecules, named EF24 and EF31, exhibited favorable potential in terms of inhibition of both IKKβ activity and PC cell proliferation. Aiming to enhance their cellular

  鉴于抑制性κB（IκB）激酶β（IKKβ）在胰腺癌（PC）的发展和进程中发挥着重要作用，人们认为靶向IKKβ的抑制剂作为新型抗PC疗法越来越受欢迎。就抑制IKKβ活性和PC细胞增殖而言，两种名为EF24和EF31的合成分子表现出有利的潜力。为了增强它们的细胞效力并分析它们的结构-活性关系，设计并合成了四个系列的EF24和EF31类似物。通过激酶活性和癌细胞的活力筛选，D6对IKKβ活性和PC细胞增殖均表现出出色的抑制作用。此外，多项生物学评估表明，D6直接与IKKβ结合，并显着抑制肿瘤坏死因子-α诱导的IKKβ/核因子κB通路的激活，并有效诱导癌细胞凋亡。此外，分子对接和分子动力学模拟分析表明，D6和IKKβ之间的主导力包括疏水相互作用。总之，D6可能是PC治疗的有前途的治疗剂，它也为新型IKKβ抑制剂的设计提供了结构上的线索。
• ANTINEOPLASTIC COMPOUNDS
  申请人：DIMMOCK R. Jonathan

  公开号：US20070155733A1

  公开（公告）日：2007-07-05

  The present invention relates to 4-piperidone derivatives represented by the following formula (I) and the acid addition salts thereof. The method of preparation and antineoplastic activity of the said compounds are disclosed. A number of the compounds possess submicromolar IC 50 and CC 50 values and have a selective toxicity for colon cancers and leukemic cells. In addition, many of the compounds are able to reverse multidrug resistance.

  本发明涉及以下公式（I）所表示的4-哌啶酮衍生物及其酸盐加成物。揭示了所述化合物的制备方法和抗肿瘤活性。其中一些化合物具有亚微摩尔级别的IC50和CC50值，并具有对结肠癌和白血病细胞的选择性毒性。此外，许多化合物能够逆转多药耐药性。
• Antineoplastic compounds
  申请人：University of Saskatchewan

  公开号：US07582655B2

  公开（公告）日：2009-09-01

  The present invention relates to 4-piperidone derivatives represented by the following formula (I) and the acid addition salts thereof. The method of preparation and antineoplastic activity of the said compounds are disclosed. A number of the compounds possess submicromolar IC50 and CC50 values and have a selective toxicity for colon cancers and leukemic cells. In addition, many of the compounds are able to reverse multidrug resistance.

  本发明涉及以下式(I)所表示的4-哌啶酮衍生物及其酸加成盐。本发明还公开了所述化合物的制备方法和抗肿瘤活性。其中许多化合物具有亚微摩尔IC50和CC50值，并具有对结肠癌和白血病细胞的选择性毒性。此外，许多化合物能够逆转多药耐药性。
• Design, Synthesis and Bioevaluation of Novel<i>N</i>-Substituted-3,5-Bis(Arylidene)-4-piperidone Derivatives as Cytotoxic and Antitumor Agents with Fluorescent Properties
  作者：Jufeng Sun、Shuping Zhang、Chen Yu、Guige Hou、Xiaofan Zhang、Keke Li、Feng Zhao

  DOI：10.1111/cbdd.12254

  日期：2014.4

  Ten new N‐substituted‐3,5‐bis(arylidene)‐4‐piperidone derivatives (series 1 and 2) were synthesized and subsequently evaluated against human carcinoma cell lines SW1990, MIA PaCa‐2, PG‐BE1, NCI‐H460, and SK‐BR‐3 for cytotoxic activity by the CCK‐8 method, and their fluorescent properties were investigated as well. The compounds were confirmed to display greater cytotoxic activity to the neoplastic cells, and approximately 50% of the IC50 values were lower than 5 μm. In particular, compounds 1a, 1c, 1d, and 1e bearing 3‐bromophenyl groups were revealed as the most active antitumor drug candidates and had the average IC50 values of 1.94, 1.11, 1.16, and 0.817 μm, respectively. Furthermore, their fluorescent properties were interesting and might contribute to the visualization of their distribution in tumor cells. Some possible reasons for the disparity between cytotoxic activity and fluorescent properties in the two series of compounds were explored. This study revealed high potential of these molecules for further development as fluorescent cytotoxic and antitumor agents.