3',3''-dimethyl-3,5-bis[(E)-thienylmethylene]piperidin-4-one | 1312614-71-3

• 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: 3',3''-dimethyl-3,5-bis[(E)-thienylmethylene]piperidin-4-one
• 英文别名: 3,5-bis((3-methylthiophen-2-yl)methylene)piperidin-4-one；(3E,5E)-3,5-bis[(3-methylthiophen-2-yl)methylidene]piperidin-4-one
• CAS: 1312614-71-3
• 化学式: C₁₇H₁₇NOS₂
• 分子量: 315.46
• InChiKey: PRPSJGMNBHDXDR-FNCQTZNRSA-N

物化性质

• 熔点：
  172 °C(Solv: ethanol (64-17-5))
• 沸点：
  527.0±50.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  85.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲基噻吩醛 、 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80%的产率得到3',3''-dimethyl-3,5-bis[(E)-thienylmethylene]piperidin-4-one
  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

• 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.