ABSTRACT
An attractive approach for the preparation of spirocyclic benzofuran-furocoumarins has been developed through iodine-catalyzed cascade annulation of 4-hydroxycoumarins with aurones. The reaction involves Michael addition, iodination, and intramolecular nucleophilic substitution in a one-step process, and offers an efficient method for easy access to a series of valuable spirocyclic benzofuran-furocoumarins in good yields (up to 99%) with excellent stereoselectivity. Moreover, this unprecedented protocol provides several advantages, including readily available materials, an environmentally benign catalyst, a broad substrate scope, and a simple procedure.
ABSTRACT
An unprecedented protocol has been developed for the synthesis of 3,4-heterocycle-fused coumarins from 4-aminocoumarins and aurones through iodine-catalyzed cascade reactions. Dihydropyridine-fused coumarin, pyridine-fused coumarin, and pyrrole-fused coumarin derivatives were achieved in good yields with high selectivity when CH3CN, AcOH, and DMSO were used as the solvent, respectively. This protocol provides several advantages, such as easily available starting materials, high atom economy, friendly environment, and simple procedure.
ABSTRACT
A series of novel bisbenzofuran-imidazolium salts were designed and prepared. The in vitro antitumor activity of these derivatives was evaluated against a panel of human tumor cell lines (A549, HL-60, MCF-7, SMMC-7721 and SW480). Results demonstrated that 2-methyl-benzimidazole ring and substitution of the imidazolyl-3-position with a 4-methoxyphenacyl or 2-naphthylacyl substituent were important for promoting cytotoxic activity. Notably, compound 23 was found to be the most potent compound with IC50 values of 0.64-1.47 µM against five human tumor cell lines, and exhibited higher selectivity to MCF-7 and SW-480 cell lines with IC50 values 15.3-fold and 9.1-fold lower than DDP.
Subject(s)
Antineoplastic Agents/pharmacology , Benzofurans/pharmacology , Imidazoles/pharmacology , Antineoplastic Agents/chemical synthesis , Benzofurans/chemical synthesis , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Imidazoles/chemical synthesis , Molecular Structure , Structure-Activity RelationshipABSTRACT
A series of novel 3-benzylcoumarin-imidazolium salts were prepared and evaluated in vitro against a panel of human tumor cell lines. The results showed that the existence of 5,6-dimethyl-benzimidazole ring and substitution of the imidazolyl-3-position with a naphthylacyl group were vital for modulating cytotoxic activity. Notably, compound 38 was found to be the most potent derivative with IC50 values of 2.04-4.51 µM against five human tumor cell lines, while compound 34 were more selective to SW-480 cell lines with IC50 value 40.0-fold lower than DDP. Mechanism of action studies indicated that compound 38 can cause the G0/G1 phase cell cycle arrest and apoptosis in SMMC-7721 cell lines.
Subject(s)
Antineoplastic Agents/chemical synthesis , Coumarins/chemistry , Imidazoles/chemistry , Antineoplastic Agents/pharmacology , Apoptosis/drug effects , Cell Line, Tumor , Drug Design , Drug Screening Assays, Antitumor , G1 Phase Cell Cycle Checkpoints/drug effects , Humans , Salts/chemistry , Structure-Activity RelationshipABSTRACT
An iodine-catalyzed nucleophilic substitution reaction of xanthen-9-ol and thioxanthen-9-ol with indoles has been developed, providing an efficient procedure for the synthesis of xanthene/thioxanthene-indole derivatives with good to excellent yields. This protocol offers several advantages, such as short reaction times, green solvent, operational simplicity, easily available catalyst and mild reaction conditions. Moreover, this method showed good tolerance of functional groups and a wide range of substrates.
ABSTRACT
A simple and convenient synthesis of 3-salicyloylquinoline-4-carboxylic esters has been developed through an AlCl3-catalyzed reaction of easily available Baylis-Hillman adducts from chromones and isatin-derivatives. This reaction involves esterification, cyclization and ring opening in a one-step process, and provides an efficient approach for easy access to a series of valuable salicyloylquinoline derivatives with high yields. Moreover, this protocol offers several advantages, such as availability of starting materials, economic availability, operational simplicity and mild reaction conditions.