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  • Title: Lead optimization of 2-(piperidin-3-yl)-1H-benzimidazoles: identification of 2-morpholin- and 2-thiomorpholin-2-yl-1H-benzimidazoles as selective and CNS penetrating H₁-antihistamines for insomnia.
    Author: Ravula SB, Yu J, Tran JA, Arellano M, Tucci FC, Moree WJ, Li BF, Petroski RE, Wen J, Malany S, Hoare SR, Madan A, Crowe PD, Beaton G.
    Journal: Bioorg Med Chem Lett; 2012 Jan 01; 22(1):421-6. PubMed ID: 22153347.
    Abstract:
    The structure-activity relationships of 2-(piperidin-3-yl)-1H-benzimidazoles, 2-morpholine and 2-thiomorpholin-2-yl-1H-benzimidazoles are described. In the lead optimization process, the pK(a) and/or logP of benzimidazole analogs were reduced either by attachment of polar substituents to the piperidine nitrogen or incorporation of heteroatoms into the piperidine heterocycle. Compounds 9a and 9b in the morpholine series and 10g in the thiomorpholine series demonstrated improved selectivity and CNS profiles compared to lead compound 2 and these are potential candidates for evaluation as sedative hypnotics.
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