Neuroprotective Activity of (+)-(S)-2-[(1S,5R)-(3,7-Dioxo-2,4,6,8-Tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid

• Published in: Russian journal of bioorganic chemistry Vol. 38; no. 5; pp. 550 - 557
• Main Authors: Kravchenko, A. N., Baranov, V. V., Anikina, L. V., Vikharev, Yu. B., Bushmarinov, I. S., Nelyubina, Yu. V.
• Format: Journal Article
• Language: English
• Published: Dordrecht SP MAIK Nauka/Interperiodica 01-09-2012
• Subjects: Biochemistry; Biomedical and Life Sciences; Biomedicine; Bioorganic Chemistry; Life Sciences; Organic Chemistry; and (R,S)-N-carbamoylmethionine; racemate; R; S; 4,5-dihydroxyimidazolidine-2-one; diastereoselective synthesis; glycolurils; enantiomers; neuroprotective activity
• ISSN: 1068-1620; 1608-330X
• DOI: 10.1134/S106816201205007X

A study of the neurotropic, neuroprotective, and antioxidant action of the enantiomers and racemate of 2-[(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid synthesized in a stereoselective reaction of (
R
)-, (
S
)-, or (
R,S
)-
N
-carbamoylmethionine with 4,5-dihydroxyimidazolidine-2-one showed that only (+)-(
S
)-2-[(1
S
,5
R
)-(3,7-dioxo-2,4,6,8-tetraazabicyclo[3.3.0]oct-2-yl)]-4-methylthiobutanoic acid had neuroprotective properties. X-ray structure analysis showed that the predominating racemate of glycolurils is crystallized from aqueous solutions as a conglomerate. Antioxidant activity was not detected.