Please use this identifier to cite or link to this item: https://doi.org/10.1021/cc049910t
Title: Traceless solid-phase synthesis of nitrogen-containing heterocycles and their biological evaluations as inhibitors of neuronal sodium channels
Authors: Kong, K.-H.
Chen, Y. 
Ma, X. 
Wai, K.C. 
Lam, Y. 
Issue Date: Nov-2004
Source: Kong, K.-H., Chen, Y., Ma, X., Wai, K.C., Lam, Y. (2004-11). Traceless solid-phase synthesis of nitrogen-containing heterocycles and their biological evaluations as inhibitors of neuronal sodium channels. Journal of Combinatorial Chemistry 6 (6) : 928-933. ScholarBank@NUS Repository. https://doi.org/10.1021/cc049910t
Abstract: The preparation of pyrimidine-2-thione, pyrimidine-2-one, pyrimidine, and benzo[b][1,4]diazepine derivatives using traceless solid-phase sulfone linker strategy is described. Key steps involved are (i) sulfinate S-alkylation, (ii) sulfone anion alkylation with an epoxide, (iii) γ-hydroxyl sulfone → γ-ketosulfone oxidation, and (iv) traceless product release by a one-pot elimination-cyclization process. Elimination-cyclization was carried out under basic conditions with thiourea, methyl thiourea, methyl urea, guanidine hydrochloride, benzamidine hydrochloride and ortho-phenylene diamine. Twenty-three compounds were prepared, and 14 of them were evaluated by the Batrachotoxin (BTX) radioligand binding assay for their binding affinity to neuronal sodium channels. Compound 7c was found to be a potential neuronal sodium channels blocker.
Source Title: Journal of Combinatorial Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/53239
ISSN: 15204766
DOI: 10.1021/cc049910t
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