ABSTRACT
The present investigation reports an easy access to a library of novel spiro-oxindole-pyrrolizine or pyrrolo[1,2-c]thiazole fused coumarin hybrid heterocycles through a one-pot sequential four-component reactions of 2,2-dimethyl-1,3-dioxane-4,6-dione, salicylaldehydes, isatins, and cyclic α-amino acids under ultrasound irradiation.
Subject(s)
Combinatorial Chemistry Techniques/methods , Coumarins/chemical synthesis , Ultrasonics/methods , Amino Acids/chemistry , Coumarins/chemistry , Heterocyclic Compounds/chemical synthesis , Indicators and Reagents , Models, Molecular , Molecular Conformation , Spiro Compounds/chemistryABSTRACT
A series of novel hybrid heterocycles comprising arylidene thiazolidine-2,4-dione and 1-cyclopropyl-2-(2-fluorophenyl)ethanone were synthesized. These compounds were evaluated for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv in High Throughput Screen. Most of the hybrid arylidene thiazolidine-2,4-diones displayed moderate to good activity with MIC of less than 50 µM. Compound 1m exhibited maximum potency being 5.87 fold more active at EC50 and 6.26 fold more active at EC90 than the standard drug pyrimethamine.
Subject(s)
Anti-Bacterial Agents/pharmacology , Mycobacterium tuberculosis/drug effects , Thiazolidinediones/pharmacology , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Dose-Response Relationship, Drug , Microbial Sensitivity Tests , Molecular Structure , Structure-Activity Relationship , Thiazolidinediones/chemical synthesis , Thiazolidinediones/chemistryABSTRACT
An efficient one-pot four-component domino protocol for the combinatorial synthesis of novel 1,4-dihydropyrano[2,3-c]pyrazol-6-amines has been achieved. This transformation presumably occurs via cyclization-Knoevenagel condensation-Michael addition-tautomerism-intramolecular O-cyclization-elimination sequence of reactions. The significant features of this reaction include expedient one-pot process, short reaction time, no column chromatographic purification, excellent yield, and readily available starting materials.
Subject(s)
Amines/chemical synthesis , Combinatorial Chemistry Techniques/methods , Pyrazoles/chemical synthesis , Amines/chemistry , Cyclization , Pyrans/chemical synthesis , Pyrans/chemistry , Pyrazoles/chemistry , StereoisomerismABSTRACT
The 1,3-dipolar cycloaddition of azomethine ylide derived in situ from the reaction of acenaphthylene-1,2-dione and 1,3-thiazolane-4-carboxylic acid to various exocyclic dipolarophiles synthesized from trans-androsterone and trans-dehydroandrosterone afforded a library of novel spiro[5'.2â³]acenaphthylene-1â³-one-spiro[16.6']-(7'-aryl)-tetrahydro-1H-pyrrolo [1,2-c][1,3]thiazolo-trans-androsterone/dehydroandrosterone hybrid heterocycles respectively. These reactions proceeded stereo-specifically affording a single isomer of the 16-spiro steroids in excellent yields.
