Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines.

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Ansari FL, Iftikhar F, Ihsan-Ul-Haq, Mirza B, Baseer M, Rashid U

Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines.

Bioorg Med Chem. 2008 Aug 15;16(16):7691-7. doi: 10.1016/j.bmc.2008.07.009. Epub 2008 Jul 9.

PubMed ID

18650096 [ View in PubMed

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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.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Galantamine	Acetylcholinesterase	IC 50 (nM)	500	N/A	N/A	Details