We have developed a method for the synthesis of novel selenophene-containing polycyclic heterocycles, derivatives of selenopheno[3,2-c]- and selenopheno[2,3-c]quinolones. The cytotoxic activity of these compounds was studied in vitro. The molecular structure of 3-bromo-5-methyl-2-(piperidin-2-ylmethyl)selenopheno[3,2-c]quinolin-4(5H)-one was confirmed by X-ray analysis.
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V. Gressler, C. Z. Stüker, G. de O. C. Dias, I. I. Dalcol, R. A. Burrow, J. Schmidt, L. Wessjohann, and A. F. Morel, Phytochemistry, 69, 994 (2008).
T. Sripisut, T. Ritthiwigrom, T. Promgool, K. Yossathera, S. Deachathai, W. Phakhodee, S. Cheenpracha, and S. Laphookhieo, Phytochem. Lett., 5, 379 (2012).
A. Gafter-Gvili, A. Fraser, M. Paul, M. D. van de Wetering, L. C. M. Kremer, and L. Leibovici, Antibiotic Prophylaxis for Bacterial Infections in Afebrile Neutropenic Patients Following Chemotherapy, Wiley Online Library (2009), DOI: 10.1002/14651858.CD004386.pub3.
B. S. Jayashree, S. Thomas, and Y. Nayak, Med. Chem. Res., 19, 193 (2010).
D. E. King, R. Malone, and S. H. Lilley, Am. Fam. Physician, 61, 2741 (2000).
T. Ohashi, Y. Oguro, T. Tanaka, Z. Shiokawa, S. Shibata, Y. Sato, H. Yamakawa, H. Hattori, Y. Yamamoto, S. Kondo, M. Miyamoto, H. Tojo, A. Baba, and S. Sasaki, Bioorg. Med. Chem., 20, 5496 (2012).
K. Goerlitzer, B. Gabriel, P. Frohberg, I. Wobst, G. Drutkowski, J. Wiesner, and H. Jomaa, Pharmazie, 59, 439 (2004).
A. V. Polishchuk, E. T. Karaseva, M. A. Medkov, and V. E. Karasev, Proceedings of Far Eastern Division of Russ. Acad. Sci., No. 2, 128 (2005).
Y.-L. Chen, US Pat. Appl. 6656949.
J. E. Spallholz, Bull. Selenium-Tellurium Develop. Assoc., 1 (2001).
H. Arvilommi, K. Poikonen, I. Jokinen, O. Muukkonen, L. Räsänen, J. Foreman, and J. K. Huttunen, Infect. Immun., 41, 185 (1983).
R. Bohm, Pharmazie, 42, 793 (1987).
P. Arsenyan, K. Rubina, I. Shestakova, and I. Domracheva, Eur. J. Med. Chem., 42, 635 (2007).
M. S. Shahabuddin, M. Nambiar, B. Choudhary, G. M. Advirao, and S. C. Raghavan, Invest. New Drugs, 28, 35 (2010).
V. Yu. Mortikov, V. P. Litvinov, A. M. Shestopalov, Yu. A. Sharanin, E. E. Apenova, G. A. Galegov, I. I. Abdullaev, T. B. Asadullaev, and F. I. Abdullaev, Khim.-Farm. Zh., 25, 5, 41 (1991). [Pharm. Chem. J., 25, 312 (1991).]
S. E. Bahaie, M. G. Assy, and M. M. Hassanier, Pharmazie, 45, 791 (1990).
J. R. Hwu, L.-L. Lai, G. H. Hakimelahi, and H. Davari, Helv. Chim. Acta, 77, 1037 (1994).
T. Ventslavskaia, L. Stazhadze, and V. Korzhova, Farmakol. Toksikol. (Moscow), 47, 38 (1984).
A. Kudrin and L. Zaidler, Farmakol. Toksikol. (Moscow), 31, 41 (1968).
V. G. Beylin, O. P. Goel, A. D. Sercel, and H. D. H. Showalter, US Pat. Appl. 4806654.
J. Zakrzewski and M. Krawczyk, Bioorg. Med. Chem. Lett., 21, 514 (2011).
S. Leycks and M. Parnham, Agents Actions, 30, 426 (1990).
P. Arsenyan, I. Shestakova, K. Rubina, I. Domracheva, A. Nesterova, K. Vosele, O. Pudova, and E. Lukevics, Eur. J. Pharmacol, 465, 229 (2003).
P. Arsenyan, E. Paegle, S. Belyakov, I. Shestakova, E. Jaschenko, I. Domracheva, and J. Popelis, Eur. J. Med. Chem., 46, 3434 (2011).
N. C. Becknell, J. A. Lyons, L. D. Aimone, J. A. Gruner, J. R. Mathiasen, R. Raddatz, and R. L. Hudkins, Bioorg. Med. Chem. Lett., 21, 7076 (2011).
Report of the International Workshop on in vitro Methods for Assembling Acute Systemic Toxicity, NIH Publication, No. 01-4499 (2001), p. 12.
D. J. Fast, R. C. Lynch, and R. W. Leu, J. Leucocyt. Biol., 52, 255 (1992).
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 64, 112 (2008).
S. Maskay, C. J. Gilmore, C. Edwards, N. Stewart, and K. Shankland, maXus. Computer Program for the Solution and Refinement of Crystal Structures, Bruker Nonius, MacScience, The University of Glasgow (1999).
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*Dedicated to Academician J. Stradiņš on the occasion of his 80th birthday.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1804-1811, November, 2013.
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Arsenyan, P., Vasiljeva, J., Shestakova, I. et al. The Synthesis and Cytotoxic Properties of Selenopheno[3,2-c]- and Selenopheno-[2,3-c]quinolones*. Chem Heterocycl Comp 49, 1674–1680 (2014). https://doi.org/10.1007/s10593-014-1419-1
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DOI: https://doi.org/10.1007/s10593-014-1419-1