ABSTRACT
A three-component cascade method has been developed for the direct synthesis of polysubstituted pyridines. This strategy provides a very convenient route to pyridines using a variety of ß-bromo-α,ß-unsaturated aldehydes, 1,3-diketones, and ammonium acetate without any additional catalyst or metal salt under mild conditions. A variety of ß-ketoesters and 4-hydroxycoumarin were also used instead of 1,3-diketones for the diverse synthesis of polycyclic pyridines. One of the synthesized pyridines has been unambiguously established by a single crystal XRD study. All of the synthesized pyridine derivatives were evaluated for their antiproliferative properties in vitro against the human cancer cell lines HeLa, Me180, and ZR751. Compounds 4{4,1} and 4{2,4} showed significant cytotoxicity in the human breast cancer cell line ZR751 and cervical cancer cell line Me180, respectively, and a few other compounds were found to have moderate activities.
Subject(s)
Antineoplastic Agents/chemical synthesis , Pyridines/chemical synthesis , Antineoplastic Agents/pharmacology , Breast Neoplasms/drug therapy , Breast Neoplasms/pathology , Cell Line, Tumor , Cell Survival/drug effects , Cytotoxins/chemistry , Cytotoxins/pharmacology , Female , Humans , Polycyclic Compounds/chemical synthesis , Polycyclic Compounds/pharmacology , Pyridines/pharmacology , Uterine Cervical Neoplasms/drug therapy , Uterine Cervical Neoplasms/pathologyABSTRACT
A facile strategy for the synthesis of steroidal A- and D-ring fused pyrimidines has been accomplished in high yields via a one-pot reaction of steroidal ketones, aromatic aldehydes and amidine derivatives in presence of potassium tert-butoxide in refluxing ethanol. The generality of the reaction was also extended to non-steroidal ketones.
Subject(s)
Pyrimidines/chemistry , Steroids/chemistry , Aldehydes/chemistry , Amidines/chemistry , Butanols/chemistry , Catalysis , Ethanol/chemistry , Ketones/chemistry , TemperatureABSTRACT
The preparation of A-ring and D-ring fused steroidal quinolines is described from one-pot reaction of steroidal ß-bromovinylaldehydes and arylamines in solvent-free and catalyst-free condition under microwave irradiation. The antimicrobial activities of the compounds were tested by agar diffusion assay and broth macro dilution method. Compounds 7a, 7e and 7g-h showed promising in vitro activity when tested against fungal pathogen Aspergillus niger whereas compounds 7e-h and 7j showed promising activity when tested against fungal pathogen Candida albicans. Compounds 7c and 7f showed potent inhibition against the growth of Gram negative bacteria Pseudomonas aeruginosa and compounds 7e, 7g-h and 7j inhibited the growth of tested Gram positive bacteria Bacillus subtilis and Staphylococcus aureus.
Subject(s)
Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Green Chemistry Technology/methods , Microwaves , Quinolines/chemical synthesis , Quinolines/pharmacology , Steroids/chemistry , Anti-Infective Agents/chemistry , Bacteria/drug effects , Chemistry Techniques, Synthetic , Fungi/drug effects , Microbial Sensitivity Tests , Quinolines/chemistryABSTRACT
The preparation of ring-A fused pyrimidines at the steroidal 2,3-position is herein described. The novel steroidal pyrimidines were prepared from the solid phase three-component reaction of 2-hydroxymethylene-3-keto steroids, arylaldehydes and ammonium acetate under microwave irradiation.
