RESUMEN
Synthesis of N- and O-acyl derivatives of DL-serine and threo-DL-phenylserine was accomplished by a regioselective acylation of the corresponding amino acid. The residues introduced into amino acid structure contain hydrophobic long chain or aromatic, namely lauroyl, myristoyl and phenylacetyl moieties. The fungicidal activity against six strains of fungi was studied. Several compounds were found to be effective against growth of fungi, and O-myristoyl-DL-serine 2 and N-phenylacetyl-threo-DL-phenylserine 8 completely inhibited the growth of the mycelium of the fungus Verticillium dahliae.
Asunto(s)
Aminoácidos/síntesis química , Aminoácidos/farmacología , Antifúngicos/síntesis química , Hidroxiácidos/síntesis química , Hidroxiácidos/farmacología , Aminoácidos/química , Antifúngicos/farmacología , Aspergillus niger/efectos de los fármacos , Botrytis/efectos de los fármacos , Hongos/efectos de los fármacos , Fusarium/efectos de los fármacos , Hidroxiácidos/química , Pruebas de Sensibilidad MicrobianaRESUMEN
Synthesis and evaluation of anti-inflammatory activity in rats with adjuvant arthritis of aryl sulfonyl derivatives of nonproteinogenic aromatic amino acids is reported. The studied compounds were synthesized by introducing residues of benzene-, p-toluene-, and p-bromobenzene sulfonic acids into threo-DL-phenylserine and erythro-DL-p-nitrophenylserine structures. From the set of 12 compounds tested in animal screening, N-(p-bromobenzenesulfonyl)-erythro-DL-p-nitrophenylserine ethyl ester 12 demonstrated the most pronounced anti-inflammatory activity. This compound inhibited inflammation process in polyarthritis phase by 53% (P < 0.001) though it was slightly toxic (LD50 > 6,000 mg kg(-1) for mice).