ABSTRACT
A series of azatricyclodiones and octahydro-benzo[f]isoindoles have been synthesized by (4+2) Diels-Alder cycloaddition of maleimides with furfuryl amine. Reaction of azatricyclodiones with isocyanates led to the respective ureides. All of the compounds were screened against a number of bacteria and fungi. One of the compounds (2) displayed moderate antitubercular activity while two compounds (2) and (4) inhibited the fungal growth at 25 µg/mL.
Subject(s)
Anti-Infective Agents/chemical synthesis , Aza Compounds/chemical synthesis , Isoindoles/chemical synthesis , Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Antitubercular Agents/chemical synthesis , Antitubercular Agents/chemistry , Antitubercular Agents/pharmacology , Aza Compounds/chemistry , Aza Compounds/pharmacology , Bacteria/drug effects , Cycloaddition Reaction , Fungi/drug effects , Isoindoles/chemistry , Isoindoles/pharmacology , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular StructureABSTRACT
A series of 2-sulfanyl-6-methyl-1,4-dihydropyrimidines (8-21) were synthesized in good yields by alkylation of 5-methyl-6-phenyl-2-thioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid ethyl esters (2-7) with different alkyl or aralkyl halides in the presence of a combination of anhydrous K(2)CO(3) and catalytic amount of tetrabutyl ammonium bromide. The title compounds were evaluated for their antifilarial activity against adult parasites of human lymphatic filarial parasite Brugia malayi (sub-periodic strain) in vitro and in vivo at various concentrations. One of the compounds (18) showed promising antifilarial activity.
Subject(s)
Brugia malayi/drug effects , Filaricides/chemical synthesis , Filaricides/pharmacology , Pyrimidines/chemical synthesis , Pyrimidines/pharmacology , Alkylation , Animals , Dose-Response Relationship, Drug , Filaricides/chemistry , Models, Molecular , Molecular Structure , Parasitic Sensitivity Tests , StereoisomerismABSTRACT
A total of 42 benzyl- and pyridylmethyl amines were synthesized either by reductive amination of aromatic/heteroaromatic aldehydes with amines or by conjugate addition of amines to the cinnamates followed by reduction of the ester group with lithium aluminium hydride to the respective propanolamines. All the synthesized compounds were evaluated against both avirulent and virulent strains of Mycobacterium tuberculosis. Many of the compounds exhibited MIC as low as 1.56microg/mL. Few of potent compounds were also evaluated against clinical isolates of MDR TB and found to be active at one or other concentrations with MIC as low as 3.12microg/mL.
Subject(s)
Amines/chemical synthesis , Amines/pharmacology , Antitubercular Agents/chemical synthesis , Antitubercular Agents/pharmacology , Drug Resistance, Multiple, Bacterial , Mycobacterium tuberculosis/drug effects , Amines/chemistry , Microbial Sensitivity Tests , Mycobacterium tuberculosis/classificationABSTRACT
Microwave-assisted extraction (MAE), ultrasound-assisted extraction (UAE) and conventional extraction of vanillin and its quantification by HPLC in pods of Vanilla planifolia is described. A range of nonpolar to polar solvents were used for the extraction of vanillin employing MAE, UAE and conventional methods. Various extraction parameters such as nature of the solvent, solvent volume, time of irradiation, microwave and ultrasound energy inputs were optimized. HPLC was performed on RP ODS column (4.6 mm ID x 250 mm, 5 microm, Waters), a photodiode array detector (Waters 2996) using gradient solvent system of ACN and ortho-phosphoric acid in water (0.001:99.999 v/v) at 25 degrees C. Regression equation revealed a linear relationship (r2 > 0.9998) between the mass of vanillin injected and the peak areas. The detection limit (S/N = 3) and limit of quantification (S/N = 10) were 0.65 and 1.2 microg/g, respectively. Recovery was achieved in the range 98.5-99.6% for vanillin. Maximum yield of vanilla extract (29.81, 29.068 and 14.31% by conventional extraction, MAE and UAE, respectively) was found in a mixture of ethanol/water (40:60 v/v). Dehydrated ethanolic extract showed the highest amount of vanillin (1.8, 1.25 and 0.99% by MAE, conventional extraction and UAE, respectively).
