1638769-15-9Relevant academic research and scientific papers
Synthesis and reactions of new chiral linear dipeptide candidates using nalidixic acid as starting material
Khalifa, Nagy M.,Naglah, Ahmed M.,Al-Omar, Mohamed A.,Amr, Abd El-Galil E.
, p. 728 - 736 (2014/07/07)
A series of dipeptide heterocyclic derivatives 4-15 were synthesized using methyl 2-{[(1-ethyl- 7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridin-3-yl)carbonyl] amino}-3-ethylbutanoate (3) as starting material. Treatment of 3 with L-phenylalanine methyl ester hydrochloride afforded the corresponding dipeptide methyl ester derivative 4, which was treated with hydrazine hydrate to afford the dipeptide acid hydrazide 5. Compound 5 was coupled with aldehyde and acetophenone derivatives to afford the corresponding Schiff bases 6a-f. The hydrazide derivative 5 was reacted with ethyl acetoacetate or acetone to give compounds 7 and 8, respectively. Reaction of 5 with carbon disulfide at different conditions afforded compounds 9 and 10, which were treated with hydrazine hydrate to give the 1-amino-2-dipeptido-1,3,4-triazole derivative 11. In addition, 5 was reacted with phenyl isothiocyanate to give the thiosemicarbazide derivative 12, which was cyclized with sodium hydroxide to the dipeptido 1-phenyl-1,3,4-triazole derivative 13. Finally, treatment of 13 with methyl iodide afforded the S-methyl derivative 14, which was reacted with hydrazine hydrate to give the hydrazine derivative 15.
