ABSTRACT
A library of quinazolinones was prepared by the one-pot three-component reaction of isatoic anhydride, ammonium salts/amines, and various electrophiles using aqueous hydrotropic solution as an efficient, economical, reusable, and green medium giving good to excellent yields of products in very short time. The method offers a versatile way for the development of diversity-oriented synthesis of quinazolinones.
Subject(s)
Quinazolinones/chemistry , Quinazolinones/chemical synthesis , Water/chemistry , Amines/chemistry , Ammonium Compounds/chemistry , Catalysis , Chemistry Techniques, Synthetic , Green Chemistry Technology , Oxazines/chemistryABSTRACT
A novel series of ferrocene tagged multi-functionalized 1,4-dihydropyrimidines is synthesized by base catalyzed cyclocondensation between ferrocenyl chalcones and amidines. The structures of synthesized compounds were established on the basis of (1)H NMR, (13)C NMR, FTIR spectroscopy as well as by mass spectrometry. The compounds were evaluated for in vitro anticancer activity. The most active compounds from the series displayed GI50 value equal to doxorubicin against the strain of human breast cancer cell line MDA-MB-435.
Subject(s)
Antineoplastic Agents/pharmacology , Breast Neoplasms/drug therapy , Ferrous Compounds/chemistry , Pyrimidines/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Breast Neoplasms/pathology , Cell Line, Tumor , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Humans , Metallocenes , Molecular Structure , Pyrimidines/chemical synthesis , Pyrimidines/chemistry , Structure-Activity RelationshipABSTRACT
Ultrasound promoted synthesis of ß-amino carbonyl compounds in aqueous hydrotropic medium at ambient temperature is reported. The remarkable features of the new procedure are shorter reaction time, excellent yields in aqueous medium, cleaner reaction profile and simple experimental and work-up procedure.
