SYNTHESIS OF 4-AMINO-BENZO[F]ISOINDOLE DERIVATIVES BY REACTION 1-AMINO-2-ARYLISOINDOLES WITH MALEIMIDES: УДК 547.759.4

S. Krykun; T. Yegorova; I. Levkov; Z. Voitenko

Автор(и)

S. Krykun, Student Київський національний університет імені Тараса Шевченка
T. Yegorova, PhD Київський національний університет імені Тараса Шевченка
I. Levkov, PhD Київський національний університет імені Тараса Шевченка
Z. Voitenko, Professor Київський національний університет імені Тараса Шевченка

Ключові слова:

isoindole, rearrangement, bis-Michael adduct

Анотація

Investigated the reactivity of 1-amino-2-arylisoindoles, the main tautomeric forms for which is imine form. It is shown that the reaction of 1-amino-2-arylisoindoles with maleimides produces derivatives of 4-amino-benzo[f]isoindole. Developed two new methods for the synthesis of fluorescent derivatives of 4-amino-benzo[f]isoindole, which have several advantages relative described earlier in the literature: reaction speed, simple selection of products with high purity, better outputs.

Посилання

1. Snyder S.H. Drugs and the Brain / S.H. Snyder. – Scientific American Library: New York, 1986. – 228 p.

2. Crider A. M. Synthesis and anticancer activity of nitrosourea derivatives of phensuximide / A. M. Crider, T. M. Kolczynski, K. M. J. Yates // Med. Chem. – 1980 – V. 23. – P. 324–326.

3. Ando Y. Thalidomide Metabolism by the CYP2C Subfamily / Y. Ando, E. Fuse, W. D. Figg // Clin. Cancer Res. – 2002 – V. 8. – P. 1964–1973.

4. Freiberg C. Discovering the Mechanism of Action of Novel Antibacterial Agents through Transcriptional Profiling of Conditional Mutants / C. Freiberg, H. P. Fischer, N. A. Brunner // Antimicrob. Agents Chemother. – 2005 – V. 49. – P. 749 –759.

5. Andrimid, a new peptide antibiotic produced by an intracellular bacterial symbiont isolated from a brown planthopper / A. Fredenhagen, S. Y. Tamura, P. T. M. Kenny et al. // J. Am. Chem. Soc. – 1987. – V. 109. – P. 4409–4411.

6. Adamantyl maleimide induced changes in adhesion molecules and ROS are involved in apoptosis of human gastric cancer cells / J. J. Wang, T. Y. Liu, P. H. Yin et al. // Anticancer Res. – 2000. – V. 20, № 5A. – P. 3067–3073.

7. Pharmacology and biochemical profile of a new anorectic drug: mazindol / M.O. Carruba, F. Zambotti, L. Vicentini et al // Garattini S. Central Mechanisms of Anorectic Drugs / Garattini S. Samanin R (eds). –New York: Raven Press, 1978. – P. 145–164.

8. Benzo- and cyclohexanomazindol analogues as potential inhibitors of the cocaine binding site at the dopamine transporter / W.J. Houlihan, U.F. Ahmad, J. Koletar et al. // J. Med. Chem. – 2002. – V. 45, №19. – P. 4110–4118.

9. Benzo[f]isoindole derivatives from cycloaddition reaction of 2,4-dimethylpyrimido[2,1-a]isoindole and aleimides / Z. V. Voitenko, O. A. Pok-holenko, O. T. Ilkun et al. // C. R. Chimie. – 2006. – V. 9. – P. 1482–1487.

10. 4-Amino-benzo[f]isoindole derivatives: synthesis and fluorescence properties / I. V. Levkov, Z. V. Voitenko, O. A. Zaporozhets et al. // J. Chem. Res. – 2011. – № 4. – P. 209–213.

11. The Curtin-Hammett principle in action: 1-amino-3Н-isoindole in cycloaddition reactions / I. V. Levkov, O. V. Turov, O. V. Shishkin et al. // Tetrahedron. – 2010. – V. 66, № 2. – P. 508–512.

12. Reaction of 1-ethoxyisoindole with maleimide and its derivatives / I. V. Levkov, S. Cassel, Z. V. Voitenko et al. // Heterocycles. – 2012. – № 7. – P. 1671–1681.

13. 2-Substituted-isoindoles: a novel synthetic route and a study of the Diels-Alder and Michael reactions / Z. V. Voitenko, V. V. Sypchenko, I. V. Levkov et al. // J. Chem. Res. – 2011. – № 11. – P. 615–618.

14. Veber D. F. 1-Arylisoindoles / D. F. Veber, W. Lwowski // J. Am. Chem. Soc. – 1963. – V. 85, P. 646–647.