title: Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines.
abstract: Solid-phase synthesis of a parallel library of 3'-hydroxy-2,3-dihydrobenzothiazepines has been carried out through [4+3] annulation of alpha,beta-unsaturated ketones with aminothiophenol, using Wang resin as solid support. The synthesized compounds were evaluated for their potential as antibacterial, tumor inhibitors as well as acetyl- and butyrylcholinesterase inhibitors. None of the compounds showed any significant antibacterial activity. However, quite a few compounds showed significant potential as crown gall tumor inhibitors. These results reflect a strong exploratory potential in search of new benzothiazepines as source of anticancer agents. The results of the inhibition of cholinesterase revealed that benzothiazepines have a greater potential as butyrylcholinesterase inhibitors as compared to acetylcholinesterase. Moreover, the substitution of hydroxy group at C-3 in ring A led to increased activity when compared to unsubstituted- and 2'-OH substituted benzothiazepines.
authors.affiliation: Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan. fla_qau@yahoo.com
authors.forename: Farzana Latif
authors.initials: FL
authors.lastname: Ansari
authors.forename: Fatima
authors.initials: F
authors.lastname: Iftikhar
authors.lastname: Ihsan-Ul-Haq
authors.forename: Bushra
authors.initials: B
authors.lastname: Mirza
authors.forename: Mohammad
authors.initials: M
authors.lastname: Baseer
authors.forename: Umer
authors.initials: U
authors.lastname: Rashid
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002802:Cholinesterases / Q000378:metabolism; D020650:Combinatorial Chemistry Techniques; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D010941:Plant Tumors; D013841:Thiazepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C106746:1,5-benzothiazepine; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D002800:Cholinesterase Inhibitors; D013841:Thiazepines; D002802:Cholinesterases