Use of formylindolylacetic acid as a reagent at the stage of preparing the glycosides of bis(indolyl)furan-2,5-diones and dioxane as solvent increased yields from 5 – 10% to 60 – 63%, decreased the duration of the reaction from 6 h to 2 h, and significantly simplified extraction of products adequate for use at the next stage of photochemical oxidation to furancarbazole derivatives. New data are presented on the cytotoxic activity of the indocarbazole N-glycosides synthesized here, covering a wide range of cell structures and giving a more complete view of the antiproliferative properties of the compounds synthesized.
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References
S. Deslandes, S. Chassaing, and E. Delfourne, Mar. Drugs., 7(4), 754 – 786 (2009).
C. Asche and M. Demeunynck, Anticancer Agents Med. Chem., 7(2), 247 – 267 (2007).
Tanaka Seichi, Mitsuru Ohkubo, and Kojiri Katsuhise, J. Antibiot., 45(11), 1797 – 1798 (1992).
M. Ohkubo, Hiroshi Kawamoto, Toshiyuki Ohno, et al., Tetrahedron, 53(2), 585 – 592 (1997).
D. E. Nattleton, T. W. Doel, B. Kinshnan, et al., Tetrahedron Let., 25, 4011 – 4014 (1985).
T. Kaneko, H. Wong, J. Utzig, et al., J. Antibiot, 13, 125 – 127 (1990).
A. Atsushi Akao, Shouichi Hiraga, and Takehiko Iida, Tetrahedron, 57, 8917 – 8923 (2001).
M. Prudhomme, Cur. Med. Chem., 7(12), 1189 – 1212 (2000).
Kojiri Katsuhisa, Suzuki Hajime, Kondo Hisao, et al., Patent US 5, 437, 996, Chem. Abstr., 123, 167736q (1995).
Kojiri Katsuhisa, Suzuki Hajime, Kondo Hisao, et al., Patent EP 602, 597, Chem. Abstr., 121, 229009z (1994).
Kin Sing Lam, Daniel K. Schroeder, Jaqueline Marie Mattei, et al., Patent EP 445, 736, Chem. Abstr., 116, 82213x (1992).
Kin Sing Lam, Daniel K. Schroeder, Jaqueline Marie Mattei, et al., Patent US 5, 468, 849, Chem. Abstr., 123, 216075q (1995).
T. Kaneko, H. Wong, K. T. Okamoto, et al., Tetrahedron Let., 26, 4015 – 4018 (1985).
F. Anison, L. Belin, P. Moreau, et al., J. Med. Chem., 40, 3456 – 3465 (1997).
I. Alonso, G. Garcia-Minoz, R. Madronero, J. Het. Chem., 7(6), 1435 – 1437 (1970).
M. Gallant, J. T. Link, and S. Danishefsky, J. Org. Chem., 58, 343 – 349 (1993).
Mitsunoby O. and Yamada Y., Bul. Chem. Soc. Japan., 40, 2380 – 2382 (1967).
A. A. Bakhmedova, L. D. Garaeva, O. V. Goryunova, et al., Bioorgan. Khim., 23(8), 667 – 674 (1997).
S. Ya. Mel'nik, A. A. Bakhmedova, L. D. Garaeva, et al., Bioorgan. Khim.,22(10 – 11), 832–837 (1996).
O. V. Goryunova, G. M. Zakharchuk, O. S. Zhukova, et al., Bioorgan. Khim.,40(1), 12 – 19 (2014).
M. N. Preobrazhenskaya and N. N. Suvorov, Zh. Obshch. Khim., 30(7), 2434 – 2435 (1960).
A. A. Magnin, A. M. Stephen, and R. J. H. Davies, Tetrahedron, 28, 3069 – 3085 (1972).
M. N. Preobrazhenskaya and I. A. Korbukh, “The synthesis and reactions of pyrrole, pyrazole, triazole, indole, indazole, and benzotriazole nucleosides and nucleotides”, in: Chemistry of Nucleosides and Nucleotides, L. B. Townsend (ed.), Plenum Press, New York (1993), Vol. 3, pp. 1 – 105.
M. R. Boyl, Princip. Pract. Oncol., 2, 23 – 40 (1989).
R. U. Khabriev, Handbook for the Experimental (Preclinical) Study of New Pharmacological Substances [in Russian], Moscow (2005).
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 53, No. 7, pp. 13 – 17, July, 2019.
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Éktova, L.V., Goryunova, O.V., Eremina, V.A. et al. An Improved Method for the Synthesis of the of Indole[2,3-a]Pyrrolo[3,4-c]Carbazole-5,6-Dione N-Glycosides and their Cytotoxic Activity. Pharm Chem J 53, 604–609 (2019). https://doi.org/10.1007/s11094-019-02046-4
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DOI: https://doi.org/10.1007/s11094-019-02046-4