Synthesis and antibacterial activity of thioglycolic amino acid derivatives and dipeptides containing the 2-methyl-3,4-dihydroquinazolin-4-one moiety.
3-(2'-Chloroethyl)-2-methyl-3,4-dihydroquinazolin-4-one (I) was reacted with sodio (sodium thioglycolate) in dry dioxane and yielded compound II. By using thionyl chloride, this compound was converted to the corresponding acid chloride (III). The prepared acyl chloride (III) was allowed to interact with different alpha-amino acids such as Gly, L-Ala, L-B-Phe, DL-Asp, L-Glu, L-Thr and L-Val to give new amino acid derivatives (IVa-g). A selected C-terminal derivative of glycine (IVa) was converted into acid chloride (V). The acid chloride formed was reacted with L-Ala, L-B-Phe, DL-Asp, L-Glu, L-Thr and L-Val and yielded the new dipeptides VIa-f. The structures of the synthesized compounds were elucidated by elemental analysis and IR spectra. The prepared peptides were tested for their antimicrobial activities by comparison with tetra-cycline as a reference compound.
Atta
F M
FM
Chemistry Department, Faculty of Science, Assiut University, Egypt.
D000595:Amino Acid Sequence; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004151:Dipeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008969:Molecular Sequence Data; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013864:Thioglycolates / Q000138:chemical synthesis* / Q000494:pharmacology
C090822:3-(2'-ethylthioglycolyl)-2-methyl-3,4-dihydroquinazolin-4-one; D000900:Anti-Bacterial Agents; D004151:Dipeptides; D011799:Quinazolines; D013864:Thioglycolates