[Acyclic nucleoside analogs: synthesis and cytotoxic properties of acyl derivatives of 3'(5')-amino-3'(5')-deoxy-2',3'-secoadenosine].
Interaction of 3'-amino-3'-deoxy-2',3'-secoadenosine with the N-hydroxysuccinimide esters of nicotinic or quinaldic acids and with 1-nitroanthraquinone-2-carboxylic acid in the presence of 2-ethoxy-1-ethoxy-carbonyl-1,2-dihydroquinoline led to the corresponding amides. To obtain 5'-modified 2',3'-secoadenosine analogs, 5'-deoxy-5'-nicotinoylamido-, 5'-deoxy-5'-(quinoline-2- carbonylamido)-, and 5'-deoxy-5'-[3-(3-indolyl)propionylamido]adenosine were subjected to the periodate oxidation--sodium borohydride reduction procedure. Structures of the synthesized compounds were was confirmed by 1H NMR spectroscopy, 2',3'-Diamino-2',3'-deoxy-, 3'-deoxy-3'-(quinoline-2-carbonylamido)-, and 5'-deoxy-5'-[3-(3-indolyl)propionylamido]-2',3'-secoadenosines+ ++ exhibited a cytotoxic effect on CaOv cells in vitro (CE50 10-30 microM).
Goriunova
O V
OV
Iartseva
I V
IV
Ivanova
T P
TP
Mashalova
N A
NA
Kikot'
B S
BS
Mel'nik
S Ia
SIa
D000215:Acylation; D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010051:Ovarian Neoplasms / Q000473:pathology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D000241:Adenosine
Atsiklicheskie analogi nukleozidov: sintez i tsitotoksicheskie svoĭstva atsil'nykh proizvodnykh 3'(5')-amino-3'(5')-dezoksi-2',3'-sekoadenozina.