期刊
TETRAHEDRON
卷 59, 期 38, 页码 7473-7480出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(03)01206-7
关键词
acylation; density functional theory; prodrugs; regioselectivity; sulfonamides
Acylation of antimalarial and bacteriostatic sulfonamides with N-protected amino acids and peptides was carried out using standard peptide coupling methods. These acylation reactions are regioselective for the N-4 nitrogen atom of diazine-containing sulfonamides. In contrast, only N-1 coupling was found for sulfisoxazole, an isoxazole-based sulfonamide. Computational studies suggest that a combination of geometrical, thermodynamic and electronic factors are responsible for the different reactivities reported. (C) 2003 Elsevier Ltd. All rights reserved.
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