3'-deoxyribofuranose derivatives of 1-deaza and 3-deaza-adenosine and their activity as adenosine deaminase inhibitors.
2,6-Dichloro-1-deazapurine and 2,6-dichloro-3-deazapurine were coupled with 1,2-O-diacetyl-5-O-benzoyl-3-deoxy-beta-D-ribofuranose. Deprotection of the obtained compounds and reaction with liquid ammonia gave the desired 2-chloroadenine nucleosides, which were dechlorinated to afford the corresponding 1-deaza and 3-deazaadenosine derivatives. Biological studies performed on ADA from calf intestine showed that these new nucleosides are inhibitors of the enzyme.
Costanzi
S
S
Dipartimento di Biologia M.C.A., University of Camerino, I-62032, Camerino, Italy.
Lambertucci
C
C
Volpini
R
R
Vittori
S
S
Lupidi
G
G
Cristalli
G
G
D000241:Adenosine / Q000031:analogs & derivatives* / Q000494:pharmacology; D058892:Adenosine Deaminase Inhibitors; D000818:Animals; D002417:Cattle; D003855:Deoxyribose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D007422:Intestines / Q000201:enzymology; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013056:Spectrophotometry, Ultraviolet
D058892:Adenosine Deaminase Inhibitors; D004791:Enzyme Inhibitors; D003855:Deoxyribose; D000241:Adenosine