(3E,5E)-3,5-bis(2-thienylmethylene)-4-piperidone

• 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(2-thienylmethylene)-4-piperidone
• 英文别名: 3,5-bis[(E)-thienylmethylene]piperidin-4-one；3,5-bis(thiophen-2-ylmethylene)piperidin-4-one；(3E,5E)-3,5-bis(thiophen-2-ylmethylidene)piperidin-4-one
• 化学式: C₁₅H₁₃NOS₂
• 分子量: 287.406
• InChiKey: HAMFEFSJOFWARR-MKICQXMISA-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：

  (3E,5E)-3,5-bis(2-thienylmethylene)-4-piperidone 在 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 diethyl (E)-[1′-methyl-2,4′′-dioxo-4’-(thiophen-2-yl)-5’’-(thiophen-2-ylmethylene)dispiro[indoline-3,2′-pyrrolidine-3′,3′′-piperidin]-1′′-yl]phosphonate
  参考文献：
  名称：

  Spiroindole-containing compounds bearing phosphonate group of potential Mpro-SARS-CoV-2 inhibitory properties

  摘要：

  DOI：

  10.1016/j.ejmech.2023.115563
• 作为产物：
  描述：

  2-噻吩甲醛 、 4-氧代哌啶酮盐酸盐 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以82%的产率得到(3E,5E)-3,5-bis(2-thienylmethylene)-4-piperidone
  参考文献：
  名称：

  3,5-双[（E）-噻吩基亚甲基]哌啶-4-酮的1 H和13 C NMR谱研究

  摘要：

  已记录了3,5-双[（E）-噻吩基亚甲基]哌啶丁-4-酮（1a），3'，3''-二甲基-3,5-双[（E）-的1 H和13 C NMR光谱噻吩基亚甲基]哌啶丁-4-酮（1b），5'，5″-二溴-3,5-双[（E）-噻吩基亚甲基]哌啶丁-4-酮（1c），其1-甲基衍生物2a – c和3 ，5-双[（E）-噻吩基亚甲基] -2r，6c-二苯基哌啶-4-酮（3a）。对于选定的化合物，已记录了2D光谱。光谱数据用于研究这些分子的构型和构象。根据空间，电子和磁各向异性效应来讨论化学位移。噻吩环和苯基的磁各向异性效应是值得注意的。2b的1 H– 1 H COZY光谱表明，可以进行多达7个键的长距离1 H– 1 H偶联。2b的HMBC光谱显示C-2和C-6以及这些碳原子上的质子的磁非等价性。

  DOI：

  10.1016/j.saa.2010.12.062

文献信息

• A highly efficient method for solvent-free synthesis of bis(arylmethylidene)piperidinones
  作者：M. Saeed Abaee、Mohammad M. Mojtahedi、Roholah Sharifi、M. MehdiZahedi

  DOI：10.1002/jhet.5570440639

  日期：2007.11

  remarkably efficient double crossed aldol condensation of piperidin-4-one with various aromatic aldehydes is described at room temperature in the presence of diethylamine and lithium perchlorate under solvent-free conditions. Excellent yields of 3,5-bis(arylmethylidene)piperidinones are achieved in a facile one-pot general procedure. Structure of the products is determined by spectroscopic methods and elemental

  在室温下，在无溶剂条件下，在二乙胺和高氯酸锂的存在下，哌啶-4-酮与各种芳族醛的高效双酚醛缩合反应非常有效。通过简单的一锅通用方法即可获得3,5-双（芳基亚甲基）哌啶酮的优异收率。产品的结构通过光谱方法和元素分析确定。
• Synthetic Approaches to Cytotoxic Amidophosphates, Aminophosphonates, and Aminobisphosphonates with 3,5-Bis(arylidene)piperid-4-one Framework
  作者：Mikhail V. Makarov、Evgenia S. Leonova、Ekaterina V. Matveeva、Ekaterina Yu. Rybalkina、Gerd-Volker Röschenthaler、Tatiana V. Timofeeva、Irina L. Odinets

  DOI：10.1080/10426507.2010.514308

  日期：2011.3.31

  bisphosphonates having a 3,5-bis(arylidene)piperid-4-one backbone have been elaborated starting from piperid-4-ones functionalized with phosphorus motives followed by aldol-crotonic condensation with a range of (hetero)aromatic aldehydes or via introduction of the corresponding phosphorus function into the preformed NH-3,5-bis(arylidene)piperid-4-ones. Combination of phosphorus-containing moieties possessing inherent

  摘要 一些新型酰胺磷酸酯、ω-氨基膦酸酯和具有 3,5-双（亚芳基）哌啶-4-one 骨架的双膦酸酯的简便合成方法已经从用磷动机功能化的哌啶-4-酮开始阐述，然后是醛醇-巴豆与一系列（杂）芳香醛缩合或通过将相应的磷官能团引入预先形成的 NH-3,5-双（亚芳基）哌啶-4-酮。具有固有生物活性和细胞毒性 3,5-双（亚芳基）哌啶-4-one 部分的含磷部分的组合导致化合物对人癌细胞系 Caov3、A549、Scov3、PC3、KB 3-1 具有高抗肿瘤活性和 KB 8-5（IC50 在 1-80 μM 范围内）。
• 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。
• Synthesis, characterization and structure–activity relationship of novel N-phosphorylated E,E-3,5-bis(thienylidene)piperid-4-ones
  作者：Michael V. Makarov、Evgeniya S. Leonova、Ekaterina Yu. Rybalkina、Paul Tongwa、Victor N. Khrustalev、Tatiana V. Timofeeva、Irina L. Odinets

  DOI：10.1016/j.ejmech.2009.11.041

  日期：2010.3

  In order to design the agents with improved antitumor activity of 3,5-bis(thienylidene)piperid-4-one type, E,E-N-phosphoryl-3,5-bis(thienylidene)piperid-4-ones 6a-c and E,E-N-omega-phosphorylalkyl-3,5-bis-(thienylidene)piperid-4-ones 7a-c were obtained via the direct phosphorylation of the parent NH-3,5-bis(thienylidene)piperid-4-one and by condensation of preformed N-phosphorylalkyl substituted piperidones with thiophene 2-carbaldehyde, respectively. The structures of the compounds were elucidated by H-1, P-31 C-13 NMR along with a single crystal X-ray diffraction analysis. Under the action of visible light thermodynamically more stable E,E-isomers slowly undergo photochemical conversion in CDCl3 solution to the corresponding E,Z-isomers and E,Z-N-methyl-3,5-bis(thienylidene)piperid-4-one 5 was isolated in individual state. The importance of phosphorylation for cytotoxic properties of 3,5bis(thienylidene)piperid-4-ones towards human carcinoma cell lines Caov3, Scov3, and A549 and influence of olefin configuration on antitumor activity were demonstrated. (C) 2009 Elsevier Masson SAS. All rights reserved.
• Curcumin analogues as possible anti-proliferative & anti-inflammatory agents
  作者：A.-M. Katsori、M. Chatzopoulou、K. Dimas、C. Kontogiorgis、A. Patsilinakos、T. Trangas、D. Hadjipavlou-Litina

  DOI：10.1016/j.ejmech.2011.03.060

  日期：2011.7

  A series of novel curcumin analogues has been designed, synthesized and tested in vitro/in vivo as potential multi-target agents. Their anti-proliferative and anti-inflammatory activities were studied. Compounds 1b and 2b were stronger inhibitors of soybean lipoxygenase (LOX) than curcumin. Analogue 1b was also the most potent aldose reductase (ALR2) inhibitor. Two compounds, (1a and 1f) exhibited in vivo anti-inflammatory activity comparable to that of indomethacin, whereas derivative 1i exhibited even higher activity. The derivatives were also tested for their anti-proliferative activity using three different human cancer cell lines. Compounds 1a, 1b, 1d and 2b exhibited significant growth inhibitory activity as compared to curcumin, against all three cancer cell lines. Lipophilicity was determined as R-M values using RPTLC and theoretically. The results are discussed in terms of the structural characteristics of the compounds. Docking simulations were performed on LOX and ALR2 inhibitor 1b and curcumin. Compound 1b is well fitted in the active site of ALR2, binding to the ALR2 enzyme in a similar way to curcumin. Allosteric interactions may govern the LOX-inhibitor binding. (C) 2011 Elsevier Masson SAS. All rights reserved.