Ring opening reactions: synthesis of AICAR analogs as potential antimetabolite agents.
In an attempt to improve the AzA selectivity of the 2-(aryl)alkylthio derivatives of adenosine, we planned the synthesis of the corresponding derivatives of the 5-N-ethylcarboxamidoadenosine (NECA). For this purpose, we designed the synthesis of 2-mercapto-NECA to be pursued by means of an opening-closure method We obtained the open AICAR analog; however, ring closure efforts failed to give the desired compound. The newly synthesized AICAR derivative could potentially be endowed with antiviral or antitumoral activity.
Costanzi
S
S
Dipartimento di Scienze Chimiche, University of Camerino, Camerino, Italy.
Lambertucci
C
C
Portino
F R
FR
Volpini
R
R
Vittori
S
S
Cristalli
G
G
D019830:Adenosine-5'-(N-ethylcarboxamide) / Q000138:chemical synthesis / Q000494:pharmacology; D000620:Aminoimidazole Carboxamide / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000963:Antimetabolites / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D008956:Models, Chemical; D012265:Ribonucleotides / Q000138:chemical synthesis* / Q000494:pharmacology
D000963:Antimetabolites; D000970:Antineoplastic Agents; D000998:Antiviral Agents; D012265:Ribonucleotides; D019830:Adenosine-5'-(N-ethylcarboxamide); D000620:Aminoimidazole Carboxamide; C031143:AICA ribonucleotide