A synthesis of useful intermediate, 2-(azidomethyl)-5-bromobenzofuran starting from
5-bromobenzofuran-2-carboxylic acid is described. The reaction of 5-bromo-2-(iodomethyl)benzofuran
with sodium azide affords 2-(azidomethyl)-5-bromobenzofuran. 5-Bromo-2-(iodomethyl)benzofuran
was obtained from a combination of consecutive 5-bromobenzofuran-2-carboxylic acid reactions
involving NaBH4 reduction followed by the iodination of the resulting alcohol. The utility of
2-(azidomethyl)-5-bromobenzofuran has been demonstrated for the preparation of a novel series of
1-((5-bromobenzofuran-2-yl-)methyl)-4-substituted phenyl-1H-1,2,3-triazoles in excellent yields. The
newly synthesized compounds have been characterized and evaluated for antimicrobial activities against
Gram-negative and Gram-positive bacterial strains.
A series of 5-(5-bromobenzofuran-2-yl)-substituted 1,3,4-oxadiazole-
2-thiol derivatives (4a-d) and substituted benzylidene-3-methyl-1-
(5-bromobenzofuran-2-carbonyl)-1H-pyrazol-5(4H)-one derivatives
(6a-d) have been synthesized in good yields and characterized by IR
and NMR analyses. Auto Dock 4.0/ADT program was used to investigate
binding interaction of oxadiazole and pyrazole derivatives to
DNA GyrB. DNA gyrase of Mycobacterium tuberculosis (MTB) is a
type II topoisomerase and well-established and validated target for
the development of novel therapeutics. The search was based on the
Lamarckian genetic algorithm and the results were analyzed using
binding energy. Analysis was based on lowest docked energy and inhibition
constant values. Among the tested compounds 4b, 6b and 6c
derivatives of oxadiazole and pyrazole showed highest binding energy
with the lowest inhibition constant. From the observed results, it is
concluded that compounds 4b, 6b and 6c showed more affinity to
DNA GyrB protein.
Objective: To develop a novel, accurate, precise and linear reverse phase high performance liquid chromatographic (RP-HPLC) method for simultaneous quantitative estimation of ramipril, atorvastatin and clopidogrel in Atamra-CV tablet and validate as per international conference on harmonization (ICH) guidelines and to perform the force degradation studies using the developed method.Methods: In the present work, the good chromatographic separation was achieved isocratically using a shim-pack HPLC Kromasil 150 mm x 4.6 mm, 5 m. m. And mobile phase consisting of 0.05 M potassium dihydrogen orthophosphate pH 3 adjusted with orthophosphoric acid and acetonitrile in the ratio (52:48), at flow rate 1 ml/min and column temperature (30 °C). The effluents obtained were monitored at 210 nm with the UV-visible detector.Results: The retention time of ramipril, atorvastatin and clopidogrel was found to be 2.893 min, 5.012 min and 6.102 min respectively. The linearity of ramipril, atorvastatin and clopidogrel was found in the range of 25-150 % and the correlation coefficient for ramipril, atorvastatin and clopidogrel were>0.999. The high recovery values (98%-101%) indicate a satisfactory accuracy. The low percent relative standard deviation (% RSD) values in the precision study reveals that the method is precise. The three-drug samples were subjected to stress conditions of acidic and alkaline hydrolysis, oxidation, photolysis and thermal degradation. The proposed method proved to be stability-indicating by resolution of the analytes from their forced-degradation products.Conclusion: The developed method is novel, simple, precise, rapid, accurate and reproducible for simultaneous estimation of ramipril, atorvastatin and clopidogrel tablet dosage form. Hence the proposed method may find practical applications as a quality-control tool in the simultaneous analysis of the three drugs in combined dosage forms in quality-control laboratories. The proposed method was made use of photodiode array (PDA) as a tool for peak identification and purity confirmation.
The six benzofuran-oxadiazole derivatives (4a-d) and (5a-b) have been designed, synthesized, characterized and evaluated for antimicrobial activity. The key synthetic intermediate 5-bromo-N'-hydroxybenzofuran -2-carboxamidine (3) was prepared from 5-bromobenzofuran-2-carboxylic acid (1) in two consecutive steps involving reaction with NaN3, in presence of TEA, Xtalfluor-E, PPh3 in dry DCM at 0oC followed by the treatment of resulting carbonitrile (2) with hydroxylamine hydrochloride in presence of sodium methoxide under reflux in aqueous ethanol. Reaction of carboxamidine (3) with different aryl esters in presence of K2CO3 under reflux conditions in toluene afforded 3-(5-bromobenzofuran-2-yl)-5-substituted phenyl-1,2,4-oxadiazoles (4a-d) while the refluxion of a solution of carboxamidine (3) in dichloromethane with chloro/bromo acetyl chloride in presence of TEA and a catalytic amount of HBTU furnished 3-(5-bromobenzofuran-2-yl)-5-(chloromethyl)-1,2,4-oxadia zole (5a) and 3-(5-bromobenzofuran-2-yl)-5-(bromomethyl)-1,2,4-oxadiazole (5b).
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