Synthesis and X-ray crystal structure study of the hydroxyurea and hydantoin derivatives of L-valine.
The novel hydroxyurea 5 derivative of L-valine was prepared by aminolysis of N-(1-benzotriazolecarbonyl)-L-valine cyclohexanemethylamide 4 with hydroxylamine. The corresponding hydantoin derivative 6 was synthesized by base catalyzed cyclization of the amide 4. The exact stereostructure of hydantoin derivative 6 has been determined by X-ray crystal structure analysis. The chiral atom of the hydantoin ring in 6 has S configuration what is in agreement with its configuration in the starting L-valine. The molecules of 6 are joined into infinite chains by N-H...O intermolecular hydrogen bond. The infinite chains are additionally linked by two C-H...O hydrogen bonds, thus forming two-dimensional network. The hydantoin derivative of L-valine 6 and its L-leucine analogue LH have similar packing arrangements, so they are homostructural.
Department of Medicinal Chemistry, Faculty of Pharmacy and Biochemistry, A. Kovacića 1, HR-10000 Zagreb, Croatia.
N
N
Opacić
B
B
Zorc
M
M
Cetina
D
D
Mrvos-Sermek
S
S
Raić-Malić
M
M
Mintas
D018360:Crystallography, X-Ray; D006827:Hydantoins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006860:Hydrogen Bonding; D006918:Hydroxyurea / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014633:Valine / Q000737:chemistry*
D006827:Hydantoins; D014633:Valine; D006918:Hydroxyurea