Synthesis and Cytotoxic Activity of Indolo[2,3-a]Pyrrolo[3,4-c]Carbazole-5,7-Dione N-Glycosides Substituted on the Maleimide Nitrogen Atom

Reactions of indolo[2,3- a ]furano[3,4- c ]carbazole-5,7-diones with hydrazine hydrate, hydroxylamine hydrochloride, and formyl hydrazine produced the corresponding N -6-substituted indolopyrrolocarbazole glycosides with the carbohydrate residues L-arabinose, D-galactose, D-xylose, and D-ribose. The...

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Published in:Pharmaceutical chemistry journal 2020-08, Vol.54 (5), p.455-458
Main Authors: Ektova, L. V., Eremina, V. A., Tikhonova, N. I., Plikhtyak, I. L., Medvedeva, L. A., Yartseva, I. V., Moiseeva, N. I., Golubeva, I. S., Yavorskaya, I. P., Bud’ko, A. P., Tarasova, O. I., Pugacheva, R. B.
Format: Article
Language:English
Subjects:
Leukemia
Medicine
Monosaccharides
Nitrogen
Organic Chemistry
Pharmacology/Toxicology
Pharmacy
Resveratrol
Sugars
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Summary:Reactions of indolo[2,3- a ]furano[3,4- c ]carbazole-5,7-diones with hydrazine hydrate, hydroxylamine hydrochloride, and formyl hydrazine produced the corresponding N -6-substituted indolopyrrolocarbazole glycosides with the carbohydrate residues L-arabinose, D-galactose, D-xylose, and D-ribose. The obtained compounds were studied in vitro and in vivo and showed significant antiproliferative activity against HCT-116 cells (IC 50 = 10 –6 – 10 –7 M) and high antitumor effects on Ehrlich ascites tumor and P-388 lymphocytic leukemia models. The lifespan increase of animals in the first model ranged from 540 – 495% to 172 – 132%; in the second model, from 80 – 83% to 120 – 93%.
ISSN:0091-150X
1573-9031
DOI:10.1007/s11094-020-02222-x