Background Pyridines have been reported to possess various pharmacological activities. Results Sodium 3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-en-1-olate (2) and sodium 3-oxo-3-(3-oxo-3H-benzo[f]chromen-2-yl)prop-1-en-1-olate (7) were prepared and reacted with 2-cyano-N'-(1-aryl(heteryl)ethylidene)acetohydrazides 3a-d to produce 2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives 5a-d and 9a-d, respectively, in good yields. Also, 3a-d reacted with sodium (2-oxocyclopentylidene)methanolate (11a) or sodium (2-oxocyclohexylidene) methanolate (11b) to yield 2-oxo-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitriles 13a-d and 2-oxo-hexahydroquinoline-3-carbonitriles 13e-h, respectively. The mechanisms that account for the formation of the products are discussed. Additionally, the structures of all the newly synthesized products are confirmed, based on elemental analysis and spectral data. Several of the newly synthesized compounds are evaluated for their antitumor activity against HEPG2 and their structure activity relationship (SAR) was studied. Conclusions The results revealed that the pyridine derivatives 5c and 5d (IC50 = 1.46, 7.08 µM, respectively) have promising antitumor activity against liver carcinoma cell line (HEPG2), compared to the reference drug, doxorubicin.

中文翻译：

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新型 3-氰基吡啶的简便合成和抗增殖活性。

背景 据报道，吡啶具有多种药理活性。结果钠 3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-en-1-olate (2) 和钠 3-oxo-3-(3-oxo-3H-benzo[制备 f]chromen-2-yl)prop-1-en-1-olate (7) 并与 2-氰基-N'-(1-aryl(heteryl)ethyleneidene)acetohydrazides 3a-d 反应生成 2-oxo -1,2-二氢吡啶-3-腈衍生物 5a-d 和 9a-d 分别以良好的收率。此外，3a-d 与 (2-氧代亚环己基) 甲醇钠 (11a) 或 (2-氧代亚环己基) 甲醇钠 (11b) 反应生成 2-氧代-四氢-1H-环戊二烯[b]吡啶-3-甲腈 13a-d和 2-氧代-六氢喹啉-3-腈 13e-h，分别。讨论了解释产物形成的机制。此外，所有新合成产物的结构都得到确认，基于元素分析和光谱数据。评估了几种新合成的化合物对 HEPG2 的抗肿瘤活性，并研究了它们的构效关系 (SAR)。结论 结果表明，与参比药物阿霉素相比，吡啶衍生物 5c 和 5d（IC50 分别为 1.46、7.08 µM）对肝癌细胞系 (HEPG2) 具有良好的抗肿瘤活性。