Syntéza salicylanilidových proléčiv

• Main Author: Krátký, Martin
• Other Authors: Vinšová, Jarmila
• Format: Dissertation
• Language: Czech
• Published: 2008
• Online Access: http://www.nusl.cz/ntk/nusl-292588

KRÁTKÝ, Martin. Synthesis of Salicylanilide Prodrugs. Hradec Králové: Faculty of Pharmacy of Charles University, 2008. 75 pp. Diploma Thesis. This diploma thesis is concerned with synthesis of antibacterial prodrugs based on esters of salicylanilides with amino acids. First there are characterized prodrugs and their importance and then biological activities and application of salicylanilides. The main goal of this work was the synthesis of prodrugs of salicylanilides amino acids esters. Some synthesized compounds were evaluated especially for their activity against atypical Mycobacteria strains. These compounds possess antimycobacterial activity, but it is lower than initial salicylanilide 5-chloro- N-(3-chlorophenyl)-2-hydroxybenzamide. This diploma thesis acknowledges rearrangement after N-deprotection and α-amino group liberation of N-protected amino acids esters with salicylanilides to furnish diamides. The diamide was esterified by Z-amino acids (L-phenylalanine and glycine). These obtained esters were N- deprotected and the amino group was liberated. After this liberation there was described rearrangement to furnish probably triamides, analogously to furnishing of diamides. There are discussed two possible mechanisms of rearrangement - with forming of seven-membered benzoxazepinedione rings...