Synthesis and Antitumor Evaluation of Some New Fused and Binary Pyridines

Abstract

in Wiley Online Library (wileyonlinelibrary.com).Syntheses of some new heterocyclic compounds containing pyridone, thioxopyridine, halogenated-pyridinecarbonitriles, pyrazolopyridine, and pyridine derivatives were achieved. Besides, a modified synthetic method for the synthesis of 2-chloro-4,6-dimethyl-nicotinonitrile (3) through the reaction of acetylacetone and malononitrile as starting materials was implemented. The reaction of 2-chloronicotinonitrile 3 with substituted amines to 2-aminonicotinonitrile were also investigated. Fused or binary pyridines were tested for cytotoxicity against well-known established model Ehrlich ascites cells in vitro. Compound 13 exhibited a high antitumor activity compared with 5-fluorouracil.

A Comparative Study on the Structural and Vibrational Properties of Two Potential Antimicrobial and Anticancer Cyanopyridine Derivatives

“…In general, the calculated shifts for the 13 C nuclei are lower than the corresponding experimental values. Note that the calculated chemical shifts for the H nuclei of (2-OH) show a significant variation (0.81 ppm) than the (2-Cl) derivative (0.22 ppm), in relation to the corresponding experimental values [2]. Probably, the theoretical calculations do not correctly predict the hydrogen chemical shift of the H19 nucleus belonging to the OH group of (2-OH), as observed in Table S8, because that group is involved in intermolecular H-bonds.…”

“…Calculated HOMO and LUMO orbitals, energy band gap, chemical potential (μ), electronegativity (χ), global hardness (η), global softness (S) and global electrophilicity index (ω) for the two studied cyanopyridine derivatives. [2]. TMS as reference.…”

“…The stability of both derivatives were studied by means of second order perturbation energies E (2) (donor  acceptor) whose values are given in Table S5. Here, we considered only those contributions higher than 20 kJ/mol.…”

“…Márquez et al 2 from a theoretical point of view the structures and vibrational properties of the 2-hydroxy-4,6-dimethylpyridine-3-carbonitrile and 2-chloro-4,6-dimethylpyridine-3-carbonitrile compounds. These cyanopyridine derivatives play a very important role in the synthesis chemistry organic and, in medicine and pharmacology because these compounds present potential anticancer, antiarrhythmic, anticonvulsant, antiparkinsonian and antimicrobial activities [2]- [8]. Recently, Waly et al have reported the synthesis and antitumor evaluation of some new fused and binary pyridines together with a modified synthetic method for the synthesis of 2-chloro-4,6-dimethyl-nicotinonitrile [2].…”

“…These cyanopyridine derivatives play a very important role in the synthesis chemistry organic and, in medicine and pharmacology because these compounds present potential anticancer, antiarrhythmic, anticonvulsant, antiparkinsonian and antimicrobial activities [2]- [8]. Recently, Waly et al have reported the synthesis and antitumor evaluation of some new fused and binary pyridines together with a modified synthetic method for the synthesis of 2-chloro-4,6-dimethyl-nicotinonitrile [2]. In other studies, the synthesis and antiarrhythmic activities of some synthesized pyridine derivatives fused with thiophene ring were also reported while new pyridine derivatives were synthesized and evaluated as analgesic, anticonvulsant and anti-parkinsonian agents [4].…”