[Synthesis and biological properties of pyrimidine 2'-deoxynucleosides modified by a residue of quinaldic acid].
O-Quinaldoyl derivatives of thymidine, 2'-deoxyuridine, and 5-trimethylsilyl-2'-deoxyuridine were synthesized. 5'-Deoxy-5'-(quinoline-2-carbonylamino)- and 5'-deoxy-5'-[(quinoline-2-carbonylamino)butyroylamino]thymidine were obtained by the reaction of 5'-amino-5'-deoxythymidine with pentafluorophenyl ester of quinaldic acid, or with 4-(quinoline-2-carbonylamino)butyric acid. Antiproliferative properties in respect to CaOv cells in vitro were found in most of the synthesized quinaldoyl derivatives of nucleosides (CE50 approximately 10(-5) M). 3'-O-Quinaldoylthymidine exhibited an antitumor activity in vivo. The interaction of 3'- and 5'-O-quinaldoyl- as well as 3',5'-di-O-quinaldoylthymidine with DNA was investigated by the method of fluorescent probes.
Ektova
L V
LV
Iartseva
I V
IV
Khorosheva
E V
EV
Ivanova
T P
TP
Iavorskaia
N P
NP
Mel'nik
S Ia
SIa
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D002645:Chickens; D004247:DNA / Q000737:chemistry / Q000187:drug effects; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006801:Humans; D009690:Nucleic Acid Conformation; D010051:Ovarian Neoplasms / Q000473:pathology; D011804:Quinolines / Q000737:chemistry*; D013936:Thymidine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D011804:Quinolines; C049107:xylure; D004247:DNA; C008898:quinaldic acid; D013936:Thymidine; D003857:Deoxyuridine
Sintez i biologicheskie svoĭstva pirimidinovykh 2'-dezoksinukleozidov, modifitsirovannykh ostatkom khinal'dinovoĭ kisloty.