Zaki Yasser H, Al-Gendey Marwa S, Abdelhamid Abdou O
Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef, 62514, Egypt.
Department of Chemistry, Faculty of Science and Humanity Studies at Al-Quwayiyah, Shaqra University, Al-Quwayiyah, 11971, Saudi Arabia.
Chem Cent J. 2018 Jun 20;12(1):70. doi: 10.1186/s13065-018-0439-9.
Chalcones have a place with the flavonoid family and show a few very important pharmacological activities. They can used as initial compounds for synthesis of several heterocyclic compounds. The compounds with the backbone of chalcones have been reported to possess various biological activities.
Pyridine and thioamide derivatives were obtained from the reaction of 3-(furan-2-yl)-1-(p-tolyl)prop-2-en-1-one with the appropriate amount of malononitrile, benzoylacetonitrile, ethyl cyanoacetate and thiosemicarbazide in the presence of ammonium acetate. The reaction of 3,5-di(furan-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide with ethyl 2-chloro-3-oxobutanoate, 3-chloropentane-2,4-dione or ethyl chloroacetate produced thiazole derivatives. Pyrano[2,3-d]thiazole derivatives were obtained as well from thiazolone to arylidene malononitrile. The structures of the title compounds were clarified by elemental analyses, and FTIR, MS and NMR spectra. Some compounds were screened against various microorganisms (i.e., bacteria +ve, bacteria -ve and fungi). We observed that compounds (3a), (4a), (4d), (5), (7) and compound (8) exhibited high cytotoxicity against the MCF-7 cell line, with IC values of 23.6, 13.5, 15.1, 9.56, 14.2 and 23.5 μmol mL, respectively, while compound (9) was displayed the lowest values against MCF-7 cell lines.
Efficient synthetic routes for some prepared pyridines, pyrazoline, thioamide, thiazoles and pyrano[2,3-d]thiazole were created. Moreover, selected newly-synthesized products were evaluated for their antitumor activity against two carcinoma cell lines: breast MCF-7 and colon HCT-116 human cancer cell lines.
查耳酮属于黄酮类化合物，具有一些非常重要的药理活性。它们可作为合成几种杂环化合物的起始化合物。据报道，具有查耳酮骨架的化合物具有多种生物活性。
在乙酸铵存在下，3-(呋喃-2-基)-1-(对甲苯基)丙-2-烯-1-酮与适量的丙二腈、苯甲酰乙腈、氰基乙酸乙酯和硫代氨基脲反应，得到吡啶和硫代酰胺衍生物。3,5-二(呋喃-2-基)-4,5-二氢-1H-吡唑-1-碳硫酰胺与2-氯-3-氧代丁酸乙酯、3-氯戊烷-2,4-二酮或氯乙酸乙酯反应生成噻唑衍生物。噻唑酮与亚芳基丙二腈反应也得到了吡喃并[2,3-d]噻唑衍生物。通过元素分析、傅里叶变换红外光谱(FTIR)、质谱(MS)和核磁共振光谱(NMR)对标题化合物的结构进行了确证。对部分化合物针对多种微生物（即革兰氏阳性菌、革兰氏阴性菌和真菌）进行了筛选。我们观察到化合物(3a)、(4a)、(4d)、(5)、(7)和化合物(8)对MCF-7细胞系表现出高细胞毒性，IC值分别为23.6、13.5、15.1、9.56、14.2和23.5 μmol·mL，而化合物(9)对MCF-7细胞系表现出最低值。
建立了一些制备吡啶、吡唑啉、硫代酰胺、噻唑和吡喃并[2,3-d]噻唑的有效合成路线。此外，对选定的新合成产物针对两种癌细胞系：人乳腺癌MCF-7和结肠癌HCT-116癌细胞系进行了抗肿瘤活性评估。
