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Title: 2,3-Diphenyltetrahydrofurans (DPTF) - A new class of stereogenic diarylheterocycles as potential COX-2 inhibitors - Computational evaluation of COX-2-DPTF binding behaviour
Authors: Singh, Palwinder
Kaur, Pervinder
Kumar, Subodh
Keywords: Cyclooxygenase;NSAIDs;diphenyltetrahydrofurans;Stereogenic molecules;Dockings
Issue Date: Jul-2006
Publisher: NISCAIR-CSIR, India
IPC Code: Int.CI.8 C07D
Abstract: Based on the reported COX-2 selectivity of α,β-diarylheterocycles based NSAIDs' - a new class of 2,3-diphenyltetrahydrofurans (DPTF) possessing COOH, CH2OH or CH2NH2 groups at C-5 and three chiral centers C-2, C-3 and C-5 have been designed. In total 12 title compounds have been studied for their binding in the active sites of COX-2 and COX-1 enzymes. For comparison, the binding behavior of known COX-2 selective (rofecoxib, celecoxib, valdecoxib) and nonselective (aspirin, ibuprofen) drugs has also been studied. The trends of COX-2 selectivity of known NSAIDs' are parallel with their reported results. In general, DPTF derivatives show binding energies in COX-2 active site better than rofecoxib and comparable to aspirin and poor binding energies in COX-1 active sites pointing towards these molecules being selective COX-2 inhibitors. The stereochemistries at C-2, C-3 and C-5 carbons of DPTF derivatives considerably affect their bindings in the active sites of COX-1 and COX-2 and the COX-2 selectivity. The ligands with configuration (2S, 3R, 5S) show higher selectivity for COX-2 over COX-1 in comparison to other configurational isomers.
Page(s): 1692-1698
ISSN: 0042-6075
Appears in Collections:IJC-B Vol.45B(07) [July 2006]

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