Condensation of β-Oxoanilide 1 with active methylene derivatives 2a,b afforded the pyridine derivative 5, and with crotononitrile afforded the pyridine 8. Compounds 9 and 11a-c were obtained by reaction of 1 with malononitrile dimer and arylidinemalononitrile 10a-10c. In contrast, when compound 1 reacted with ethoxymethylen malononitrile afforded the pyridine derivative 13. On the other hand, treatment of 1 with anthranilic acid gave the quinoline derivative 14. Also, reactions of 1 with isothiocyanate derivatives afforded compounds 16-18. The reaction of 1 with chalcone derivative afforded the pyridine derivative 22. Treatment of compound 1 with thiourea produced pyrimidine derivative 23. Furthermore, compound 1 converted into pyrimidinethione 24a and pyrimidinone 24b on treatment with a mixture of aromatic aldehydes and thiourea or urea respectively. Reaction of 24a with hydrazonyl halide, thiosemicarbazide and arylidinecyanothioacetamide afforded compounds 26, 28 and 29. Compound 29 was treated with chloroacetonitrile to afford compound 30. Six compounds from the newly synthesized were screened for antibacterial and antifungal activity against bacteria Staphylococcus aureus, Bacillus cereus and Klebsiella pneumonia and fungi Aspergillus flavus and Aspergillus ochraceous, respectively. Some of the tested compounds showed significant antimicrobial activity. IR, 1 H NMR, mass spectral data, and elemental analysis elucidated the structures of all the newly synthesized compounds.
The novel cyanothioformamides 2a-d were prepared by treatment of isothiocyanatosulfonamides 1a-d with potassium cyanide at room temperature. Cyclocondensation of compounds 2b,c with phenyl isocyanate as electrophile furnished the corresponding imidazolidines 3a,b. The reactivity of compound 3a towards some nitrogen nucleophiles was investigated. Thus, the thiosemicarbazone 4 and imidazo[4,5-b]quinoxaline 6 were synthesized by condensation of compound 3a with thiosemicarbazide and o-phenylenediamine, respectively. Treatment of 3a with hydrochloric acid afforded compound 7. Our investigation was extended to include the reactivity of cyanothioformamide 2 towards o-aminophenol, anthranilic acid, and o-phenylenediamine and yielded the corresponding heterocycles 9, 11 and 13 derivatives, respectively. Structures of the synthesized compounds were established by their elemental analysis and spectral data.
A new series of quinoline derivatives 5–12 were efficiently synthesized via one-pot multicomponent reaction (MCR) of resorcinol, aromatic aldehydes, β-ketoesters, and aliphatic/aromatic amines under solvent-free conditions. All products were obtained in excellent yields, pure at low-cost processing, and short time. The structures of all compounds were characterized by means of spectral and elemental analyses. In addition, all the synthesized compounds 5–12 were in vitro screened for their antioxidant and antibacterial activity. Moreover, in silico molecular docking studies of the new quinoline derivatives with the target enzymes, human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, were achieved to endorse their binding affinities and to understand ligand–enzyme possible intermolecular interactions. Compound 9 displayed promising antioxidant and antibacterial activity, as well as it was found to have the highest negative binding energy of -9.1 and -9.3 kcal/mol for human NAD (P)H dehydrogenase (quinone 1) and DNA gyrase, respectively. Further, it complied with the Lipinski’s rule of five, Veber, and Ghose. Therefore, the quinoline analogue 9 could be promising chemical scaffold for the development of future drug candidates as antioxidant and antibacterial agents.
In this study different Mixtures of natural plants (Artemisia monosperma Del. and Phlomis floccose L.) in different proportions and different concentrations of the mixture are used to obtain new natural dyes and applying them to woolen fabric using microwave radiation and then studying the effect of extraction time and the pH of the dyeing bath on the strength of color and then studying the fastness of these dyes against light and Washing and perspiration
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