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Uses of ethyl benzoyl acetate for the synthesis of thiophene, pyran, and pyridine derivatives with antitumor activities
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-08-03 , DOI: 10.1002/jhet.4112 Bishoy A. Ibrahim 1 , Rafat M. Mohareb 1
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-08-03 , DOI: 10.1002/jhet.4112 Bishoy A. Ibrahim 1 , Rafat M. Mohareb 1
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The N‐(arly)propanamide derivatives 3a,b were used for a series of heterocyclization reactions to give thiophene, pyran, and pyridine derivatives. Thus, these compounds underwent the Gewald's thiophene synthesis through their reactions with either malononitrile or ethyl cyanoacetate and elemental sulfur to afford compounds 6a‐f, respectively. In addition, they were subjected through a series of multicomponent reactions (MCRs) to give pyran and fused derivatives. The reactions of 3a,b with either malononitrile or ethyl cyanoacetate gave pyridine derivatives 14a‐d, respectively. The latter compounds afforded arylhydrazone derivatives 15a‐m through their reactions with any of the aromatic diazonium salts 15a‐c. The antitumor of the synthesized compounds against A549 (nonsmall cell lung cancer), H460 (human lung cancer), HT‐29 (human colon cancer), and MKN‐45 (human gastric cancer cancer) cancer cell lines together with foretinib as the positive control by a MTT assay was measured, and the results obtained showed that many compounds exhibited high potency against the six cancer cell lines.
中文翻译：
醋酸苯甲酰乙酯用于合成具有抗肿瘤活性的噻吩，吡喃和吡啶衍生物
所述ñ - （阿尔利）丙酰胺衍生物3A，3B被用于一系列heterocyclization反应，得到噻吩，吡喃和吡啶衍生物。因此，这些化合物通过与丙二腈或氰基乙酸乙酯和元素硫反应，分别进行了Gewald噻吩合成，得到化合物6a-f。另外，使它们经历一系列的多组分反应（MCR），得到吡喃和稠合衍生物。3a，b与丙二腈或氰基乙酸乙酯的反应分别得到吡啶衍生物14a-d。后者化合物可提供15a-m的芳基derivatives衍生物通过与任何芳族重氮盐15a-c反应。合成的化合物对A549（非小细胞肺癌），H460（人类肺癌），HT-29（人类结肠癌）和MKN-45（人类胃癌）癌细胞系的抗肿瘤作用与foretinib一起为阳性通过MTT测定法测定对照，并且获得的结果表明许多化合物对六种癌细胞系表现出高效力。
更新日期：2020-08-03
中文翻译：
醋酸苯甲酰乙酯用于合成具有抗肿瘤活性的噻吩，吡喃和吡啶衍生物
所述ñ - （阿尔利）丙酰胺衍生物3A，3B被用于一系列heterocyclization反应，得到噻吩，吡喃和吡啶衍生物。因此，这些化合物通过与丙二腈或氰基乙酸乙酯和元素硫反应，分别进行了Gewald噻吩合成，得到化合物6a-f。另外，使它们经历一系列的多组分反应（MCR），得到吡喃和稠合衍生物。3a，b与丙二腈或氰基乙酸乙酯的反应分别得到吡啶衍生物14a-d。后者化合物可提供15a-m的芳基derivatives衍生物通过与任何芳族重氮盐15a-c反应。合成的化合物对A549（非小细胞肺癌），H460（人类肺癌），HT-29（人类结肠癌）和MKN-45（人类胃癌）癌细胞系的抗肿瘤作用与foretinib一起为阳性通过MTT测定法测定对照，并且获得的结果表明许多化合物对六种癌细胞系表现出高效力。
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