ABSTRACT
A library of bis(azolyl)sulfonamidoacetamides was prepared by the reaction of azolylsulfonylamines with azolylchloroacetamides in the presence of pyridine/4-(dimethylamino)pyridine (DMAP) under ultrasonication. The reaction proceeded well with DMAP, resulting in a higher yield of the products. The antimicrobial activity of the compounds indicated that N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl)amino}-2-oxoethyl)sulfamoyl]-4-phenylthiazol-2-yl}benzamide (22a), N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chlorophenyl)thiazol-2-yl}benzamide (22c), and N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chloro-phenyl)-1H-imidazol-2-yl}benzamide (24c) exhibited a low minimal inhibitory concentration (MIC) against Bacillus subtilis, equal to the standard drug, chloramphenicol. Compounds 22c and 24c also showed low MICs against Aspergillus niger, equal to the standard drug, ketoconazole. The molecular properties of the synthesized molecules were studied to identify druglikeness properties of the target compounds. On the basis of molecular properties prediction, 19a, 19b, 20b, 20c, 21a-c, 22b, 22c, and 23a-c can be treated as drug candidates.
Subject(s)
Acetamides/pharmacology , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Sulfonamides/pharmacology , Acetamides/chemical synthesis , Acetamides/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Aspergillus niger/drug effects , Bacillus subtilis/drug effects , Chloramphenicol/pharmacology , Ketoconazole/pharmacology , Microbial Sensitivity Tests , Structure-Activity Relationship , Sulfonamides/chemical synthesis , Sulfonamides/chemistryABSTRACT
A convenient and facile methodology for N-sulfonylation of heteroaryl amines with ethyl chlorosulfonylacetate in the presence of dispersed sodium in THF under ultrasonication is reported. The corresponding heteroaryl sulfonamido esters are directly condensed with heteroaryl amines to get amido sulfonamido heteroaromatics in the presence of a mild base in THF under ultrasonication. Utilization of easy reaction conditions, shorter reaction times, and isolation of products in high yields under ultrasonication make this process as economically viable. The compounds 12c, 12d, 12f and 13f are potential antibacterial agents against B. subtilis and the compounds 12f, 13c and 13f are potential antifungal agents against A. niger.
Subject(s)
Amides/pharmacology , Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Heterocyclic Compounds/pharmacology , Sulfonamides/pharmacology , Ultrasonics , Amides/chemical synthesis , Amides/chemistry , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Aspergillus niger/drug effects , Bacillus subtilis/drug effects , Dose-Response Relationship, Drug , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/chemistry , Microbial Sensitivity Tests , Molecular Structure , Structure-Activity Relationship , Sulfonamides/chemical synthesis , Sulfonamides/chemistryABSTRACT
Benzylidenehydrazinyl imidazoles (3) are prepared from 2-hydrazinyl imidazoles (2) on treatment with hydrazine. The imine functionality in 3 is utilized to develop 5'-aryl-N-(4-aryl-1H-imidazol-2-yl)-1H-1,2,3-triazol-1-amines (5) by 1,3-dipolar cycloaddition of diazomethane followed by aromatization with I2 in DMSO. Compounds 3 are also explored to prepare 4'-aryl-1-(4-aryl-1H-imidazol-2-ylamino)-3-chloroazetidin-2-ones (6) on treatment with chloroacetyl chloride. The Molinspiration calculations predicted that 3, 5 and 6 have molecular hydrophobicity, conformational flexibility, good intestinal absorption and bioactivity scores. The chloro, bromo and nitro substituted imidazolyl azetidinones (6c, 6d, 6f) and nitro substituted imidazolyl triazole (5f) exhibited excellent antibacterial activity on B. subtilis, whereas chloro and nitro substituted imidazolyl triazoles (5c, 5f) showed prominent antifungal activity on A. niger.
Subject(s)
Anti-Infective Agents/chemical synthesis , Azetidines/chemistry , Schiff Bases/chemistry , Triazoles/chemistry , Anti-Infective Agents/pharmacology , Azetidines/pharmacology , Fungi/drug effects , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Imidazoles/chemistry , Microbial Sensitivity Tests , Protein Kinases/chemistry , Protein Kinases/metabolism , Schiff Bases/pharmacology , Structure-Activity Relationship , Triazoles/pharmacologyABSTRACT
Amino-linked benzoxazolyl/benzothiazolyl/benzimidazolyl quinazolines were prepared and their antimicrobial activity studied. The nitro-substituted benzothiazolyl quinazoline (8f) may be a potential antibacterial agent against Staphylococcus aureus and nitro-substituted benzimidazolyl quinazoline (9f) may be a potential antifungal agent against Aspergillus niger.
Subject(s)
Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Aspergillus niger/drug effects , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Quinazolines/chemistry , Amines/chemistry , Anti-Infective Agents/chemistry , Benzimidazoles/chemistry , Benzothiazoles/chemistry , Benzoxazoles/chemistry , Microbial Sensitivity Tests , Staphylococcus aureus/drug effectsABSTRACT
A new class of N-azole substituted thiomorpholine derivatives were prepared and their antioxidant and cytotoxic activities were studied. The methyl substituted oxazolyl thiomorpholine dioxide 9b exhibited radical scavenging activity greater than the standard ascorbic acid. On the other hand, the thiazolyl thiomorpholine 10c having a chloro substituent on the aromatic ring was identified as a remarkable lead molecule for cytotoxic activity against A549 and HeLa cells, with IC50 values of 10.1 and 30.0 µM, respectively.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Antioxidants/chemical synthesis , Antioxidants/pharmacology , Azoles/chemical synthesis , Azoles/pharmacology , Morpholines/chemical synthesis , Morpholines/pharmacology , Cell Proliferation/drug effects , Cell Survival/drug effects , Dose-Response Relationship, Drug , HeLa Cells , Humans , Inhibitory Concentration 50 , Molecular Structure , Structure-Activity RelationshipABSTRACT
A variety of bis heterocycles, oxazolyl/thiazolyl/imidazolyl oxadiazoles having a styryl sulfonylmethyl group at the 5-position of oxadiazole and tris heterocycles having a pyrrolyl/pyrazolyl sulfonylmethyl group at the 5-position of oxadiazole were prepared adopting simple and versatile synthetic methodologies. All the compounds were screened for their antioxidant activities. Compound 5b displayed radical scavenging activity in all the three methods greater than the standard ascorbic acid, whereas compounds 8b and 14b showed activities equal to the standard ascorbic acid.
Subject(s)
Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/pharmacology , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/pharmacology , Ascorbic Acid/pharmacology , Benzothiazoles/chemistry , Biphenyl Compounds/chemistry , Drug Design , Molecular Structure , Nitric Oxide/chemistry , Picrates/chemistry , Structure-Activity Relationship , Sulfonic Acids/chemistryABSTRACT
A new class of mono and bis heterocycles-styrylsulfonylmethyl 1,3,4-oxadiazoles, pyrazolyl/isoxazolyl-1,3,4-oxadiazoles were prepared and studied their antioxidant activity. The compound methyl substituted 2-(p-methylphenylamino-sulfonylmethyl)-5-[Z-(p-methylstyrylsulfonylmethyl)]-1,3,4-oxadiazole displayed slightly higher antioxidant activity than the standard ascorbic acid.
Subject(s)
Antioxidants/chemistry , Antioxidants/pharmacology , Oxadiazoles/chemistry , Oxadiazoles/pharmacology , Antioxidants/chemical synthesis , Biphenyl Compounds/chemistry , Hydrogen Peroxide/chemistry , Methylation , Nitric Oxide/chemistry , Oxadiazoles/chemical synthesis , Picrates/chemistry , Pyrazoles/chemical synthesis , Pyrazoles/chemistry , Pyrazoles/pharmacology , Sulfones/chemical synthesis , Sulfones/chemistry , Sulfones/pharmacologyABSTRACT
A new class of sulfonamidomethane pyrrolyl-oxadiazoles/thiadiazoles and pyrazolyl-oxadiazoles/thiadiazoles was prepared from arylsulfonylaminoacetic acid hydrazides and E-cinnamic acid. The lead compounds were tested for antimicrobial and cytotoxic activities. The thiadiazole compounds having chloro substituent on the aromatic ring 4c, 8c and 10c exhibited comparable antibacterial activity against Pseudomonas aeruginosa and also antifungal activity against Penicillium chrysogenum. The styryl oxadiazole compound 3c showed appreciable cytotoxic activity on A549 lung carcinoma cells which can be used as a lead compound in the future studies.
Subject(s)
Anti-Infective Agents/chemical synthesis , Heterocyclic Compounds/chemistry , Oxadiazoles/chemical synthesis , Sulfonamides/chemistry , Anti-Infective Agents/pharmacology , Anti-Infective Agents/toxicity , Cell Line, Tumor , Cell Survival/drug effects , Heterocyclic Compounds/pharmacology , Heterocyclic Compounds/toxicity , Humans , Microbial Sensitivity Tests , Oxadiazoles/chemistry , Oxadiazoles/toxicity , Penicillium chrysogenum/drug effects , Pseudomonas aeruginosa/drug effects , Structure-Activity Relationship , Sulfonamides/chemical synthesis , Sulfonamides/toxicity , Thiadiazoles/chemistryABSTRACT
A variety of sulfonamidomethane linked 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were prepared and tested for antioxidant activity. The methyl substituted arylsulfonylaminomethyl-1,3,4-oxadiazole 9b showed excellent antioxidant activity.
Subject(s)
Antioxidants/chemical synthesis , Oxadiazoles/chemistry , Thiadiazoles/chemistry , Antioxidants/chemistry , Hydrogen Peroxide/chemistry , Nitric Oxide/chemistry , Oxadiazoles/chemical synthesis , Oxidation-Reduction , Sulfonamides/chemistry , Thiadiazoles/chemical synthesisABSTRACT
A new class of acetamidomethylsulfonyl bis heterocycles-oxazolyl-1,3,4-oxadiazoles, -thiazolyl-1,3,4-oxadiazoles, and -imidazolyl-1,3,4-oxadiazoles were synthesized from the synthetic intermediates, methyl 2-((4-aryloxazol-2-ylcarbamoyl)methylsulfonyl)acetate, methyl 2-((4-arylthiazol-2-ylcarbamoyl)methylsulfonyl)acetate, and methyl 2-((4-aryl-1H-imidazol-2-ylcarbamoyl)methylsulfonyl)acetate. All the title compounds were tested for their antioxidant activity. The oxadiazolylmethylsulfonyloxazolylacetamide displayed excellent radical-scavenging activity when compared with the standard ascorbic acid.
Subject(s)
Antioxidants/chemical synthesis , Antioxidants/pharmacology , Imidazoles/chemical synthesis , Imidazoles/pharmacology , Oxadiazoles/chemical synthesis , Oxadiazoles/pharmacology , Ascorbic Acid/chemistry , Benzothiazoles/chemistry , Biphenyl Compounds/chemistry , Molecular Structure , Nitric Oxide/chemistry , Picrates/chemistry , Structure-Activity Relationship , Sulfonic Acids/chemistryABSTRACT
A new class of mono and bis heterocycles, sulfonylmethaneamido linked oxazoles, thiazoles, imidazoles, pyrrolyl oxazoles, pyrrolyl thiazoles and pyrrolyl imidazoles were prepared adopting simple and versatile synthetic methodologies. The compound chloro substituted imidazolyl styrylsulfonylacetamide is the most potent antimicrobial agent particularly against Pseudomonas aeruginosa and Penicillium chrysogenum.
Subject(s)
Anti-Bacterial Agents/pharmacology , Azoles/pharmacology , Penicillium chrysogenum/drug effects , Pseudomonas aeruginosa/drug effects , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Azoles/chemical synthesis , Azoles/chemistry , Dose-Response Relationship, Drug , Microbial Sensitivity Tests , Molecular Structure , Structure-Activity RelationshipABSTRACT
A new O-prenylated flavonol, 3',4'-dimethoxy-7-(γ,γ-dimethylallyloxy)flavonol (1), together with three known compounds, 2'-hydroxy-3,4-dimethoxychalcone (2), biochanin A (3) and kaempferol-3-O-ß-D-glucopyranoside (4), were isolated from the roots of Sophora interrupta Bedd. The structure of compound 1 was elucidated by extensive 1D and 2D NMR spectral studies.
Subject(s)
Flavonols/isolation & purification , Plant Extracts/analysis , Plant Roots/chemistry , Sophora/chemistry , Flavonols/chemistry , Hexanes , India , Magnetic Resonance Spectroscopy , Molecular Structure , PrenylationABSTRACT
A new class of mono- and bis-heterocycles, 2-arylsulfonylaminosulfonylmethyl-5-styrylsulfonylmethyloxadiazoles, pyrazolyl oxadiazoles, and isoxazolyl oxadiazoles, were synthesized and tested for their antioxidant activity. The styrylsulfonylmethyloxadiazole 5b showed good antioxidant activity when compared with the standard ascorbic acid.
Subject(s)
Antioxidants/chemical synthesis , Heterocyclic Compounds/chemical synthesis , Antioxidants/chemistry , Antioxidants/pharmacology , Biphenyl Compounds/chemistry , Free Radicals/chemistry , Heterocyclic Compounds/chemistry , Heterocyclic Compounds/pharmacology , Hydrogen Peroxide/chemistry , Molecular Structure , Nitric Oxide/chemistry , Oxidation-Reduction , Picrates/chemistry , Structure-Activity RelationshipABSTRACT
Two new flavonoids, (2S)-3',4',5'-trimethoxyflavanone (1) and 2'-hydroxy-2,4-dimethoxy-4'-O-[(E)-3,7-dimethyl-2,6-octadienyl]chalcone (2), together with a known pterocarpene, flemichapparin B (3), and a known rotenoid, dehydrodeguelin (4), were isolated from the seeds of Derris scandens. Their structures were determined by means of extensive 1D and 2D NMR spectral studies.
Subject(s)
Derris/chemistry , Flavanones/chemistry , Flavonoids/chemistry , Seeds/chemistry , Flavanones/isolation & purification , Flavonoids/isolation & purification , Magnetic Resonance Spectroscopy , Plant Extracts/chemistry , Spectrometry, Mass, Electrospray Ionization , Spectrophotometry, Infrared , Spectrophotometry, UltravioletABSTRACT
A series of novel heterocycles, bisbenzoxazolyl/benzothiazolyl/benzimidazolyl pyrazoles/isoxazoles/pyrimidines were synthesized and evaluated for their antioxidant activity. The bisbenzoxazolylisoxazole 10 exhibited good antioxidant activity when compared with the standard ascorbic acid.
Subject(s)
Drug Design , Free Radical Scavengers/chemical synthesis , Heterocyclic Compounds/chemical synthesis , Benzothiazoles , Biphenyl Compounds/chemistry , Free Radical Scavengers/chemistry , Free Radical Scavengers/pharmacology , Heterocyclic Compounds/chemistry , Heterocyclic Compounds/pharmacology , Molecular Structure , Nitric Oxide/chemistry , Picrates/chemistry , Structure-Activity Relationship , Sulfonic Acids/chemistry , Thiazoles/chemistryABSTRACT
The reactivity of gem cyanoester ketene dithiolates towards the development of a variety of heterocycles was studied and tested for antioxidant property. The compounds bis benzoxazolylmethylthiomethylene pyrazoles and isoxazoles displayed excellent radical scavenging activity when compared with the standard ascorbic acid.
Subject(s)
Antioxidants/chemistry , Ethylenes/chemistry , Heterocyclic Compounds/chemistry , Ketones/chemistry , Sulfhydryl Compounds/chemistry , Antioxidants/chemical synthesis , Ascorbic Acid/chemistry , Heterocyclic Compounds/chemical synthesis , Isoxazoles/chemistry , Pyrazoles/chemistryABSTRACT
A new class of pyrrolyl/pyrazolyl arylaminosulfonylmethyl 1,3,4-oxadiazoles, 1,3,4-thiadiazoles, and 1,2,4-triazoles were prepared and tested for antimicrobial activity. Amongst the tested compounds, 5c displayed high antimicrobial activity.
Subject(s)
Anti-Infective Agents/chemistry , Anti-Infective Agents/pharmacology , Oxazoles/chemistry , Oxazoles/pharmacology , Thiadiazoles/chemistry , Thiadiazoles/pharmacology , Triazoles/chemistry , Triazoles/pharmacology , Anti-Infective Agents/chemical synthesis , Bacteria/drug effects , Bacterial Infections/drug therapy , Fungi/drug effects , Humans , Microbial Sensitivity Tests , Mycoses/drug therapy , Oxazoles/chemical synthesis , Thiadiazoles/chemical synthesis , Triazoles/chemical synthesisABSTRACT
A new class of hitherto unknown trisheterocycles, bisoxadiazolyl/bisthiadiazolyl pyrimidinetriones/thioxopyrimidinediones was prepared in a one-pot reaction and their antimicrobial activity was studied.
Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Pyrimidines/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Antifungal Agents/chemical synthesis , Antifungal Agents/chemistry , Heterocyclic Compounds/chemical synthesis , Heterocyclic Compounds/chemistry , Heterocyclic Compounds/pharmacology , Microbial Sensitivity Tests , Oxadiazoles/chemical synthesis , Oxadiazoles/chemistry , Oxadiazoles/pharmacology , Pyrimidines/chemical synthesis , Pyrimidines/chemistry , Structure-Activity RelationshipABSTRACT
A new class of sulfone-linked bis heterocycles, methyl-3-(4'-aryl-1'H-pyrazol-3'-ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (8), methyl-3-(1'-phenyl-3',5'-diaryl-1'H-pyrazol-4'-ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (9) and methyl-3-(3',5'-diarylisoxazol-4'-ylsulfonyl)-4-aryl-3H-pyrrole-3-carboxylate (10) were prepared by the regioselective reaction of methyl-3-aryl-2-(E-arylethenesulfonyl)acrylate (2) with tosylmethyl isocyanide followed by fuctionalization of olefin moiety with 1,3-dipolar reagents. The lead compounds were tested for their antimicrobial activity.
Subject(s)
Acrylates/chemistry , Anti-Bacterial Agents/chemical synthesis , Antifungal Agents/chemical synthesis , Isoxazoles/pharmacology , Pyrazoles/pharmacology , Pyrroles/pharmacology , Sulfones/chemistry , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Cyanides/chemistry , Isoxazoles/chemical synthesis , Isoxazoles/chemistry , Microbial Sensitivity Tests , Pyrazoles/chemical synthesis , Pyrazoles/chemistry , Pyrroles/chemical synthesis , Pyrroles/chemistry , Stereoisomerism , Structure-Activity RelationshipABSTRACT
A new class of bis heterocycles, oxazolyl/thiazolyl selenadiazoles, thiadiazoles and diazaphospholes were prepared from phenacylsulfonylacetic acid methyl ester and tested for their antimicrobial and antioxidant properties.