An Efficient One‐Pot Synthesis of Highly Substituted Pyridone Derivatives and Their Antimicrobial and Antifungal Activity

Abstract

A series of carboxamide and cyano functionalized pyridone derivatives 4a-q have been synthesized via one-pot synthesis of various aldehydes 1a-q, acetoacetanilide 2, and cyanoacetamide 3. The reaction was simple and afforded pyridone derivatives in good yield, 89 to 93%. The novel pyridone derivatives were achieved by Hantzch one-pot synthesis. Moreover, the synthesized compounds were screened against Gram-positive and Gram-negative bacteria and fungi for their activity. Among them, compound 4c shows highest inhibition at 4.25 mm against Staphylococcus aureus and 3.75 mm against Escherichia coli Grampositive and Gram-negative bacteria, respectively.

Efficient synthesis and biological evaluation of some new series of pyridine derivatives: Promising and potent new class of anticancer agents

“…The IR spectra for compounds 2-4 revealed the disappearance of absorption bands at 3148, 1629 cm À1 that representing NH and C=O groups also 1 H NMR confirmed the absence of singlet signal at δ 12.68 ppm corresponding to NH proton and displayed singlet signal at δ 5.21 ppm for CH 2 protons, singlet signal at δ 4.21 ppm referring to O-CH 3 protons and (triplet signal at δ 1.53-1.55 ppm, quartet signal at δ 4.67-4.69 ppm for CH 3 -CH 2 protons, respectively) for compounds 2-4. In addition, 13 C NMR showed the disappearance of signal that characteristic of C=O group at δ 162.5 ppm and showed the appearance of signals at δ 50.9 and 54.5 ppm characteristic for CH 2 and O-CH 3 , respectively and signals at 14.5, 63.2 ppm for ethyl group. As well as the mass spectrum showed a molecular ion peak at m/z 339 (M + ; 46%), at m/z 314 (M + ; 89%) and at m/z 328 (M + ; 100%) for compounds 2-4, respectively.…”

“…The IR (KBr, v max cm À1 ) of compound 5 showed absorption bands at 1772 cm À1 , 1629 cm À1 characteristic for (C=O, acetyl) and (C=O, pyridine), respectively and its 1 H NMR showed three singlet signals at δ 2.39, 2.42, 2.46 ppm representing the presence of three methyl groups and 13 C NMR displayed signals at δ 21.03, 21.48, 21.52 ppm for (3CH 3 ), at δ 159.9 for (C=O, pyridine) and at δ 168.3 for (C=O, acetyl). Hydrolysis of nicotinonitrile 1a was performed in the presence of conc.…”

“…Furthermore, pyridine derivatives of different heterocyclic compounds have shown an important pharmacological properties like antifungal, antitubercular, antibacterial, antimicrobial, insecticidal. [10,11] It was reported that heterocyclic pyridine derivatives have a broad range of significant biological activities such as antimicrobial, [12][13][14][15] antiviral, [16][17][18] antioxidant, [19][20][21] cytotoxic with anticancer, and antitumor activities. [22][23][24][25][26][27][28] The desire for pyridine and its derivatives has further increased over the last 50 years by the discovery of many bioactive compounds containing pyridine by several companies.…”

“…[29,30] From this point of view, in this study we synthesized some of novel pyridine derivatives using the pyridine-3-carbonitrile 1a-c as a key starting material. The new synthesized compounds were identified by infrared spectroscopy (FTIR), Nuclear Magnetic Resonance ( 1 H-NMR, 13 C-NMR), Mass spectrometry (MS), and elemental analysis also their physical properties were determined such as color and melting point. In addition, their cytotoxicity was evaluated against three cancer cell lines including breast (MCF-7), colon (HCT-116), and ovarian (SKOV3), and all results were discussed.…”

Synthesis of some new Aryl-azo derivatives clubbed with Pyridone and evaluating their Biological Broadcast.

“…Where, 2-pyridone skeleton "dominant tautomer of 2-hydroxypyridine" is correspondingly existent in DNA and RNA particles [8]. Meanwhile, Pyridone analogues have pharmaceutical and an extensive assortment of pharmacological efficacies [9]. They display antibacterial [10], antifungal [11], anti-HIV [12], anticancer activities [13].…”