N6-dipeptide derivatives of N12-ribosyl-indolo[2,3-a]carbazole

N 6-derivatives of N 12-indolo[2,3- a ]pirrolo[3,4- c ]carbazole-5,7-dione are synthesized as potential antitumor agents. The pyrrol N 6 atom of these compounds is included into the dipeptide residue of the general formula > N 6-(CH 2 ) n -CO-Ala/βAla-OMe ( n = 2 or 3). These compounds are synthe...

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Bibliographic Details
Published in:Russian journal of bioorganic chemistry 2014, Vol.40 (1), p.9-15
Main Authors: Goryunova, O. V., Zakharchuk, G. M., Zhukova, O. S., Fetisova, L. V., Kuzmina, N. E.
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biomedicine
Bioorganic Chemistry
Life Sciences
Organic Chemistry
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Summary:N 6-derivatives of N 12-indolo[2,3- a ]pirrolo[3,4- c ]carbazole-5,7-dione are synthesized as potential antitumor agents. The pyrrol N 6 atom of these compounds is included into the dipeptide residue of the general formula > N 6-(CH 2 ) n -CO-Ala/βAla-OMe ( n = 2 or 3). These compounds are synthesized by the reaction in DMF at 130°C between 13-methyl-12-(2,3,4-tri- O -acetyl-β-D-ribopyranosyl)indolo[2,3- a ]furano[3,4- c ]carbazole-5,7-dione and dipeptides containing the free N -terminal amino group. The nitrogen atom of the peptide amino group replaces O6 in the furan ring and is embedded as the N 6 imide nitrogen atom of pyrrol. The ability of the compounds obtained to inhibit the growth of the SKOV3 human ovarian carcinoma cells was studied. The only derivative containing the > N 6-(CH 2 ) 3 -CO- L -Ala-OMe radical showed the cytotoxic activity with an inhibitory concentration of IC 50 = 8 μM.
ISSN:1068-1620
1608-330X
DOI:10.1134/S106816201401004X