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ABSTRACT:
Purpose: The article is aimed to synthesize, characterize and screen the biological activity of a series of N-(((5-(3- chloro-2-oxo-4-(4-(trifluoromethyl)phenyl)azetidin-1-yl)quinolin-8-yl)oxy)methyl)substitutedcarboxamide (4a-e) / N- (((5-(4-oxo-2-(4-(trifluoromethyl)phenyl) thiazolidin-3-yl)quinolin-8-yl)oxy)methyl)substitutedcarboxamide (5a-e) / N-(((5-(5-(4-(trifluoromethyl)phenyl)-1H-tetrazol-1-yl)quinolin-8-yl)oxy)methyl)substituted-1-carboxamide (6a-e).
Methods: The newly synthesized compounds were characterized by elemental analysis and IR, 1H-NMR, 13C NMR and Mass spectral data. The antimicrobial activity of the novel compounds was screened by agar disc diffusion method.
Results: 4b, 4c, 5b, 6b and 6c have shown better antibacterial and anti fungal activity than other compounds of the series.
KEYWORDS: Quinoline, ureides, azetidin-2one, thiazolidin-4-one, tetrazole.
INTRODUCTION:
Ureido derivatives are one of the oldest classes of bioactives, widely used as anti-infective agents. Many of them exhibit antibacterial1-4, antimicrobial5-6, anti-viral activities7-9. Azetidin-2-ones are very important class of compounds possessing wide range of biological activities such as antimicrobial10,11, pesticidal12, antitumor13, antitubercular14, anticancer15, cytotoxic16-18, enzyme inhibitors19, elastase inhibitors20 and cholesterol absorption inhibitors21. 4-thiazolidinones moiety is associated with variety of biological activities including antifungal22, antiinflammatory23, anticonvulsant24, antitubercular25, antihistaminic26. Tetrazoles and its derivatives are used for biological activities such as anti-inflammatory27, antibacterial28, antifungal29, analgesic30, anticonvulsant31, anticancer32 and antihypertensive33 activities.
Hence it was thought worthwhile to synthesise some new congeners of ureides by incorporating the quinoline, azetidin-2-one, thiazolidin-4-one and tetrazole moieties in a single molecular frame work.
EXPERIMENTAL:
Melting points were determined on open capillaries using a cintex melting point apparatus. T.L.C analyses were performed on precoatedsilicagel (E-Merck Kieselgel 60F254) plates and visualisation was done by exposing to iodine vapour. Solvents were purified by standard procedures before use. IR Spectra were recorded in KBr on Perkin- Elmer Spectrum BX series FT-IR spectrometer. 1H-NMR spectrum were recorded on DRX 300MHz Bruker spectrometers using TMS as internal standard (chemical shifts in δ ppm). 13C-NMR Spectra were recorded on a Brucker 75MHz spectrometer. Mass spectra were scanned on a varian MATCH-7 at 70ev. Elemental analysis was carried out on a carlo erba 106 and Perkin-Elmer Analyser. All the chemicals used in the present investigation were purchased from Sigma-aldrich, India.
Reagents and Conditions:
(i) THF / MeOH / H2O in 1:1:1 ratio, 2N NaOH, reflux, 6- 7h. (ii) Isobutyl chloroformate, acetone, TEA, Aq NaN3, - 150C, 20-30 minutes (iii) Benzene, reflux, 16h.
General procedure for the synthesis of acids by esters hydrolysis (2a-c)
In the present investigation the required synthons...