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Abstract
A series of novel pyridine and fused pyridine derivatives have been prepared starting from 6-(3,4-dimethylphenyl)-2-hydrazinyl-4-(thiophen-2-yl)-pyridine-3-carbonitrile 1 which on treatment with appropriate formic acid, acetic acid/acetic anhydride, benzoyl chloride and/or carbon disulfide afforded the corresponding triazolopyridine derivatives 2–5. Also, treatment of hydrazide 1 with diethyloxalate, chloroacetyl chloride, chloroacetic acid and/or 1,2-dichloroethane yielded the corresponding pyridotriazine derivatives 7–10. Further transformation of compound 1 with a different active methylene group, namely acetyl acetone, diethylmalonate, ethyl cyanoacetate, ethyl benzoylacetate and/or ethyl acetoacetate, produced the pyridine–pyrazole hybrid derivatives 11–15. These newly synthesized compounds (1–15) were subjected to in silico molecular docking screenings towards GlcN-6-P synthase as the target protein. The results revealed moderate to good binding energies of the ligands on the target protein. All the newly prepared products exhibited antimicrobial and antioxidant activity.
Highlights
Pyridine derivatives have received great attention because of their presence in various drugs and biologically active molecules [1,2,3,4]
In the course of our investigation, we have found that 6-(3,4-dimethylphenyl)-2-hydrazinyl4-(thiophen-2-yl)-pyridine-3-carbonitrile [62] is an excellent building block for the synthesis of a numerous heterocyclic ring systems
This study focused on the synthesis of new nicotinonitrile derivatives which were synthesized and characterized using spectral and elemental analyses
Summary
Pyridine derivatives have received great attention because of their presence in various drugs and biologically active molecules [1,2,3,4]. We found that heterocyclic compounds implicate the pyridine nucleus and showed wide promising biological activities such as anti-cancer [5,6,7], anti-oxidant [8,9], anti-microbial [5,9,10] and anti-viral [2] activities. The literature reports that pyridine derivatives are potent anti-inflammatory [11,12,13,14], Ca2+ channel antagonists [15], anti-cancer [16,17,18], anti-plasmodial [19], anti-microbial [20,21], anti-malarial [22] anti-biotic [23], analgesic [24,25], anti-oxidant [26] agents. Pyrazole hybrid heterocyclic compounds were reported as anti-bacterial [41,42,43,44], anti-inflammatory [42,43,44,45,46], anti-oxidant [46,47], anti-cancer [48,49,50] agents, etc
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