Nicotinonitrile as an essential scaffold in medicinal chemistry: an updated review (2015– present)

Abstract

Many studies have been carried out to find synthetic pathways to nicotinonitriles (3-cyanopyridines) and their analogs, which has resulted in a substantial amount of knowledge on their biological, therapeutic, and medical characteristics. Some of nicotinonitrile derivatives have emerged as marketed drugs such as bosutinib, milrinone, neratinib, and olprinone. In this review, we discuss the recently synthesized nicotinonitrile-based hybrids that possess important biological activity and will be useful for drug discovery and development.

New 6′-Amino-5′-cyano-2-oxo-1,2-dihydro-1′H-spiro[indole-3,4′-pyridine]-3′-carboxamides: Synthesis, Reactions, Molecular Docking Studies and Biological Activity

“…It is well known that the alkylation of pyridine-2-thiolates and related compounds proceed in a regiospecific way at the sulfur atom. The S-alkylation products have been proven to be multifunctional reagents for fine organic synthesis and were recognized as biologically active compounds (for reviews, see [ 1 , 6 , 9 , 10 , 11 , 90 , 91 , 92 ]).…”

“…As we can see, spiro[indole-3,4′-pyridines] 16a and 17a,b reduced the negative effect of 2,4-D on sunflower seedling hypocotyls by 16-33% and by 12-25% on sunflower seedling roots. 1 The differences are reliable at p = 0.95.…”

“…The signals in the 1 Nevertheless, the unambiguous assignment of signals in the NMR spectra of all tautomers and stereoisomers in the 17c,d system seems difficult. Additionally, the question of which tautomeric form of 17c,d is preferred in the solid state remains unclear; the presence of a strong absorption band at ν 1697-1701 cm −1 , which may be assigned to keto carbonyls, and the absence of band doubling indirectly indicate the preference of noncyclic forms.…”

“…Nicotinonitriles, nicotinamides and their partially saturated analogs represent a promising class of heterocyclic compounds with an interesting profile of biological activity (for reviews, see [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 ]). However, while nicotinonitriles have been fairly well studied, the related synthetic nicotinamides and 1,4-dihydronicotinamides have been less studied and require further investigation.…”

Design, synthesis and application of a magnetic H-bond catalyst in the preparation of new nicotinonitriles via cooperative vinylogous anomeric-based oxidation

“…These compounds have antibacterial, antifungal, antidepressant, anti-aging, anti-inammatory and anti-Alzheimer properties. [24][25][26] Also, the compounds that have pyridine nuclei in their structure have shown good medicinal properties. Pyridine derivatives have shown anti-inammatory properties and mediators involved in the inammatory process.…”