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An efficient multigram synthesis of the potent histamine H3 antagonist GT-2331 and the reassessment of the absolute configuration.

Research paper by Huaqing H Liu, Francis A FA Kerdesky, Lawrence A LA Black, Michael M Fitzgerald, Rodger R Henry, Timothy A TA Esbenshade, Arthur A AA Hancock, Youssef L YL Bennani

Indexed on: 03 Jan '04Published on: 03 Jan '04Published in: Journal of Organic Chemistry



Abstract

GT-2331 is a potent histamine H(3) antagonist which has entered clinical trials. Efficient multigram syntheses of this compound and its enantiomer are described. The literature reports that GT-2331 is the dextrorotatory (+), more potent, enantiomer of 4-[2-(5,5-dimethylhex-1-ynyl)cyclopropyl]-1H-imidazole with the absolute configuration of (1R,2R)-1. However, we found that the dextrorotatory, more potent, enantiomer of 4-[2-(5,5-dimethylhex-1-ynyl)cyclopropyl]-1H-imidazole has the (1S,2S) absolute configuration. We suggest a reconsideration of the absolute configuration of GT-2331.