[The synthesis and and study of cytotoxic activity of D-ribofuranosides and 2-deoxy-D-ribofuranosides of substituted bis(indolyl)furan, -pyrrole and indolo[2,3-alpha]carbazole derivatives].
1-(2,3,5-Tri-O-acetyl)-beta-D-ribofuranosyl indole, the key compound in the synthesis of glycosides with the bis(indole) aglycone, was obtained for the first time by the indoline-indole method. There were synthesized 3-(1-methylindol-3-yl)-4-(1-glycosylindol-3-yl)furan(or pyrrole)-2,5-diones containing the residue of beta-D-ribofuranose or 2-deoxy-beta-D-ribofuranose and analogous glycosides of indolo[2,3-a]furano(or pyrrolo)[3,4-c]carbazol-5,7-diones, which are structurally relative to the antitumor antibiotic rebeccamycin. Their cytotoxicities toward a number of human tumor cell lines were studied in vitro, and the carbazole N-glycosides were shown to be more active than the bis-(indole) glycosides. At the same time, the ribofuranosides were found to be less active than the corresponding ribopyranosides synthesized previously.
Garaeva
L D
LD
Blokhin Cancer Research Center, Russian Academy of Medical Sciences, Kashirskoe sh. 24, Moscow, 115478 Russia. chemsyn@mail.ru
Bakhmedova
A A
AA
Iartseva
I V
IV
Mel'nik
S Ia
SIa
Adanin
V M
VM
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001671:Biochemistry / Q000379:methods; D002227:Carbazoles / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007211:Indoles; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000617:Aminoglycosides; D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D002227:Carbazoles; D005663:Furans; D007211:Indoles; D011758:Pyrroles; C041514:carbazole; C053339:rebeccamycin
Sintez D-ribofuranozidov i 2-dezoksi-D-ribofuranozidov zameshchennykh bis(indolil)furana, -pirrola i indolo[2,3-alpha]karbazola i izuchenie ikh tsitotoksicheskikh svoĭstv.