Synthesis and Biological Evaluation of Amino Chalcone Derivatives as Antiproliferative Agents

Chalcone is a common scaffold found in many biologically active compounds. The chalcone scaffold was also frequently utilized to design novel anticancer agents with potent biological efficacy. Aiming to continue the research of effective chalcone derivatives to treat cancers with potent anticancer activity, fourteen amino chalcone derivatives were designed and synthesized. The antiproliferative activity of amino chalcone derivatives was studied in vitro and 5-Fu as a control group. Some of the compounds showed moderate to good activity against three human cancer cells (MGC-803, HCT-116 and MCF-7 cells) and compound 13e displayed the best antiproliferative activity against MGC-803 cells, HCT-116 cells and MCF-7 cells with IC₅₀ values of 1.52 μM (MGC-803), 1.83 μM (HCT-116) and 2.54 μM (MCF-7), respectively which was more potent than the positive control (5-Fu). Further mechanism studies were explored. The results of cell colony formatting assay suggested compound 10e inhibited the colony formation of MGC-803 cells. DAPI fluorescent staining and flow cytometry assay showed compound 13e induced MGC-803 cells apoptosis. Western blotting experiment indicated compound 13e induced cell apoptosis via the extrinsic/intrinsic apoptosis pathway in MGC-803 cells. Therefore, compound 13e might be a valuable lead compound as antiproliferative agents and amino chalcone derivatives worth further effort to improve amino chalcone derivatives’ potency.     

微波干法合成查尔酮

查尔酮的化学名为1,3-二苯基丙烯酮,以它为母体的天然化合物存在于红花、甘草等多种天然植物中,是植物体内合成黄烷酮的重要中间体,其自身也具有抗过敏、抗溃疡、抗肿瘤等药理作用[1-3].     

无溶剂、无催化剂条件下合成1,4,5,6,7,8-六氢喹啉-5-酮衍生物

无溶剂、无催化剂条件, 在NH₄OAc存在下以查尔酮和1,3-二酮为原料, 高产率地合成1,4,5,6,7,8-六氢喹啉-5-酮衍生物. 该方法具有反应条件温和、操作简单和环境友好等优点. 并通过IR, ¹H NMR, 元素分析和X衍射确证产物的结构.     

含松香骨架的手性氮杂冠醚的合成及其在不对称Michael 加成反应中的应用

以松香为原料, 合成了4个手性氮杂冠醚: N-脱氢松香基单氮杂-12-冠-4、N-脱氢松香基单氮杂-15-冠-5、N-脱氢松香基单氮杂-18-冠-6和N-降解脱氢松香基单氮杂-12-冠-4, 并用于催化不对称查尔酮Michael加成反应, 发现这些手性氮杂冠醚可以有效地催化2-硝基丙烷与查尔酮的不对称Michael加成, Michael加成产物ee最高达35%.     

新型D-π-A芘基查尔酮衍生物的合成与超快光学吸收响应

设计并合成了两种新型查尔酮衍生物1-(2,5-二甲氧基苯基)-3-(芘-1-基)丙烯酮（a）和1-(3,4-二甲氧基苯基)-3-(芘-1-基)丙烯酮（b）,其结构经IR, ¹HNMR, ¹³CNMR, LC-MS等表征。测定了化合物的紫外(UV-Vis)和荧光(FL)谱图,并对a和b进行了理论计算和热特性研究。在B3LYP/6-311+G(d,p)理论水平上对化合物a和b进行了结构优化。前线轨道分析表明：a和b分子的能隙分别为3.24 eV和3.08eV,存在分子内电荷转移现象。飞秒Z-扫描结果显示：a和b在515 nm和532 nm处表现出反饱和吸收与超快光学响应。热性能、理论计算和非线性吸收实验结果一致表明：化合物a和b在非线性光学领域有潜在应用前景。      

Synthesis and Biological Activity of 4-Hydroxy-3-(1,5-diaryl-3-oxo-pent-4-enyl)chromen-2-ones

The substituted warfarin acid chalcones have been prepared by condensation of warfarin acid and aromatic/aliphatic aldehyde using aq. NaOH as catalyst. The method is simple, cost‐effective and gives good yield in a short reaction time. All the compounds synthesized have been characterized by IR, NMR and Mass spectra. A new series of 4‐hydroxy‐3‐(3‐oxo‐1,5‐diaryl‐3‐oxo‐pent‐4‐enyl)‐chromen‐2‐ones were synthesized and submitted to biological activity. Result of the biological screening showed the compounds 3b , 3h being the most effective among the various treatments in antimicrobial screening. Compounds 3c , 3d , 3k and 3l showed moderate activity against the microorganisms tested. Compounds 3e , 3h have shown good antifungal activity.     

Synthesis and Antimicrobial Studies of Some Quinolinylpyrimidine Derivatives

The quinolinylpyrimidine derivatives were prepared by the condensation of quinolinyl chalcones with urea (or thiourea) under basic conditions by using both conventional and microwave heating. Their IR, ¹H NMR, ¹³C NMR, mass spectra and CHN analyses confirmed the prepared compounds. The newly prepared quinolinylpyrimidine derivatives were screened for antimicrobial activities against the bacterial strains viz. S. aureus, Shigella, Salmonela, P. aeroginosa, B. Subtilus and E. coli and found considerably active against S. aureus, P. aeroginosa and E. coli.     

用碲ylide合成杂环查尔酮,二烯酮和杂环烯类衍生物

最近,我们用碳酸钾作碱从碲盐在含微量甲酰胺的乙腈中,手室温条件下十分简便地合成了2-或2,4-不饱和腈,酮,酯和酰胺。杂环查尔酮和5-硝基呋喃烯类化合物都是具有生理活性的化合物。为扩大碲ylide的应用并研究杂环基团引入对碲ylide反应活性的影     

基于辛可宁的几种手性季铵盐的合成及对查尔酮的催化不对称环氧化

手性相转移催化剂;合成;醚化;不对称环氧化;查尔酮     

Semi‐synthesis and NMR spectral assignments of flavonoid and chalcone derivatives

Previous investigations of the aerial parts of the Australian plant Eremophila microtheca and Syzygium tierneyanum resulted in the isolation of the antimicrobial flavonoid jaceosidin ( 4 ) and 2′,6′‐dihydroxy‐4′‐methoxy‐3′,5′‐dimethyl chalcone ( 7 ), respectively. In this current study, compounds 4 and 7 were derivatized by acetylation, pivaloylation, and methylation reactions. The final products, 5,7,4′‐triacetoxy jaceosidin ( 10 ), 5,7,4′‐tripivaloyloxy jaceosidin ( 11 ), 5,7,4′‐trimethoxy jaceosidin ( 12 ), 2′,6′‐diacetoxy‐4′‐methoxy‐3′,5′‐dimethyl chalcone ( 13 ), 2′‐hydroxy‐4′‐methoxy‐6′‐pivaloyloxy‐3′,5′‐dimethyl chalcone ( 14 ), and 2′‐hydroxy‐4′,6′‐dimethoxy‐3′,5′‐dimethyl chalcone ( 15 ) were all fully characterized by NMR and MS. Derivatives 10 and 13 have been previously reported but were only partially characterized. This is the first reported synthesis of 11 and 14 . The natural products and their derivatives were evaluated for their antibacterial and antifungal properties, and the natural product, jaceosidin ( 4 ) and the acetylated derivative, 5,7,4′‐triacetoxy jaceosidin ( 10 ), showed modest antibacterial activity (32–128 µg/ml) against Staphylococcus aureus strains. Copyright © 2016 John Wiley & Sons, Ltd.