Abstract
A series of 5-alkyl-3-pyridylisoxazoles was synthesized using the 3-(3-pyridyl)isoxazole scaff old. All compounds of the series possessed antiaggregatory activity in the concentration range of 6•10–6–6•10–4 mol L–1. Analysis of the experimental data on the antiaggregatory activity revealed the presence of spatial constraints for the alkyl substituents in position 5 of the isoxazole ring. 5-Alkyl-3-(3-pyridyl)isoxazoles are rather selective for platelet membrane receptors.
Similar content being viewed by others
References
O. V. Demina, A. A. Khodonov, E. I. Sinauridze, V. I. Shvets, S. D. Varfolomeev, Russ. Chem. Bull., 2014, 63, 2092.
O. V. Demina, A. A. Khodonov, V. I. Shvets, S. D. Varfolomeev, Biol. Membrany [Biol. Membranes], 2002, 19, 115 (in Russian).
D. F. Woodward, R. L. Jones, S. Narumiya, Pharmacol. Rev., 2011, 63, 471.
T. Hirata, S. Narumiya, Chem. Rev., 2011, 111, 6209.
N. Nakahata, Pharmacol. Ther., 2008, 118, 18.
R. A. Coleman, W. L. Smith, S. Narumiya, Pharm. Rev., 1994, 46, 205.
R. A. Armstrong, Pharmacol. Ther., 1996, 72, 171.
M. Nakamura, T. Shimizu, Chem. Rev., 2011, 111, 6231.
B. Samuelsson, Biosci. Rep., 1983, 3, 793.
S. D. Varfolomeev, A. T. Mevkh, Biotechnol. Appl. Biochem., 1993, 17, Pt. 3, 291.
W. L. Smith, Y. Urade, P.-D. Jacobsson, Chem. Rev., 2011, 111, 5821.
O. V. Demina, Doctor of Sciences Thesis, Moscow State Institute of Fine Chemical Technology, Moscow, 2014, 598 pp. (in Russian).
Platelets in Hematologic and Cardiovascular Disorders, Eds P. Gresele, V. Fuster, J. A. Lopez, C. P. Page, J. Vermylen, Cambridge University Press, Cambridge, 2008, 511 pp.
C. Kontogiorgis, D. Hadjipavlou-Litina, Cur. Med. Chem., 2010, 17, 3162.
R. Soyka, B. D. Guth, H. M. Weisenberger, P. Luger, T. H. Muller, J. Med. Chem., 1999, 42, 1235.
R. L. Jones, M. A. Giembycz, D. E. Woodward, Brit. J. Pharmacol., 2009, 158, 104.
S. A. M. Reddy, J. Mudgal, P. Bansal, S. G. Vasanthraju, K. K. Srinivasan, C. M. Rao, N. G. Kutty, Bioorg. Med. Chem., 2011, 19, 384.
S. Das, S. Chandrasekhar, J. S. Yadav, R. Gree, Chem. Rev., 2007, 107, 3286.
H. Marusawa, H. Setoi, A. Kuroda, A. Sawada, J. Seki, Y. Motoyama, H. Tanaka, Bioorg. Med. Chem., 1999, 7, 2635.
M. Ohno, M. Miyamoto, K. Hoshi, T. Takeda, N. Yamada, A. Ohtake, J. Med. Chem., 2005, 48, 5279.
J. P. Murad, E. V. P. Espinosa, H. J. Ting, D. McClure, F. T. Khasawneh, Biochem. Biophys. Res. Commun., 2012, 421, 456.
Comprehensive Heterocyclic Chemistry, Eds A. R. Katritzky, C. W. Rees, Pergamon Press, Oxford, 1984, 1, 651 pp.
R. Huisgen, Angew. Chem., Int. Ed. Engl., 1963, 2, 565.
R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry, Ed. A. Padwa, J. Wiley, New York, 1984, 1, p. 1.
A. Sysak, B. Obminska-Mrukowicz, Eur. J. Med. Chem., 2017, 137, 292.
S. A. Lang, J. I. Lin, in Comprehensive Heterocyclic Chemistry, Eds A. R. Katritzky, C. W. Rees, K. T. Potts, Pergamon Press, Oxford, 1984, 6, Ch. 4.16, 1.
B. J. Wakefield, D. J. Wright, in Advances in Heterocyclic Chemistry, Eds A. R. Katritzky, A. J. Boulton, Academic Press, New York, 1979, 25, p. 147.
The Chemistry of Heterocyclic Compounds. Isoxazoles, Eds P. Grunanger, P. Vita-Finzi, John Wiley and Sons, New York, 1991, 49, Parts 1 and 2, p. 1.
P. Caramella, P. Grunanger, in 1,3-Dipolar Cycloaddition Chemistry, Ed. A. Padwa, J. Wiley, New York, 1984, 1, p. 291.
K. B. G. Torssell, in Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis. Novel Strategies in Synthesis, Ed. H. Feuer, VCH, Weinheim, 1988, Ch. 2, p. 55.
R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, Gazzetta Chim. Ital., 1989, 119, 253.
F. A. Lakhvich, E. V. Koroleva, A. A. Akhrem, Chem. Heterocyclic Compd., 1989, 435.
C. J. Easton, C. M. M. Hughes, G. P. Savage, G. W. Simpson, in Advances in Heterocyclic Chemistry, Eds A. R. Katritzky, A. J. Boulton, Academic Press, New York, 1994, 60, 261.
K. V. Gothelf, K. A. Jorgensen, Chem. Rev., 1998, 98, 863.
P. Caramella, D. Reami, M. Falzoni, P. Quadrelli, Tetrahedron, 1999, 55, 7027.
R. P. Litvinovskaya, V. A. Khripach, Russ. Chem. Rev., 2001, 70, 464.
A. I. Kotyatkina, V. N. Zhabinsky, V. A. Khripach, Russ. Chem. Rev., 2001, 70, 730.
Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry: Toward Heterocycles and Natural Products. The Chemistry of Heterocyclic Compounds, Eds A. Padwa, W. H. Pearson, John Wiley and Sons, New York, 2002, 59, 952 pp.
T. M. V. D. Pinho e Melo, Current Org. Chem., 2005, 9, 925.
H. Pellissier, Tetrahedron, 2007, 63, 3235.
L. I. Belen´kii, in Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis. Novel Strategies in Synthesis, Ed. H. Feuer, John Wiley and Sons Inc., Hoboken, New Jersey, 2nd ed., 2008, p. 1.
D. Giomi, F. M. Cordero, F. Machetti, in Comprehensive Heterocyclic Chemistry III, Eds A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Pergamon Press, Oxford, 2008, 4, p. 365.
I. N. N. Namboothiri, N. Rastogi, in Synthesis of Heterocycles via Cycloadditions. I. Topics in Heterocyclic Chemistry, Eds R. R. Gupta, A. Hassner, Springer-Verlag, Berlin–Heidelberg, 2008, 12, p. 1.
K. M. L. Rai, in Synthesis of Heterocycles via Cycloadditions. II. Topics in Heterocyclic Chemistry, Eds R. R. Gupta, A. Hassner, Springer-Verlag, Berlin–Heidelberg, 2008, 13, p. 1.
S. Kanemasa, Heterocycles, 2010, 82, 87.
M. Kissane, A. R. Maguire, Chem. Soc. Rev., 2010, 39, 845.
O. V. Demina, P. V. Vrzhechsh, A. A. Khodonov, V. I. Kozlovsky, S. D. Varfolomeev, Russ. J. Bioorgan. Chem., 1995, 21, 933.
O. V. Demina, A. V. Laptev, A. Yu. Lukin, N. E. Belikov, M. A. Fomin, K. V. Zvezdin, A. A. Khodonov, S. D. Varfolomeev, V. I. Shvets, Vestn. MITKhT [Bull. Moscow State Institute of Fine Chemical Technology], 2010, 5, 47 (in Russian).
Y.-Y. Ku, T. Grieme, P. Sharma, Y.-M. Pu, P. Raje, H. Mo rton, S. King, Org. Lett., 2004, 3, 4185.
P. V. Vrzhechsh, O. V. Demina, S. I. Shram, S. D. Varfolomeev, FEBS Lett., 1994, 351, 168.
O. V. Demina, A. V. Laptev, A. Yu. Lukin, A. A. Khodonov, N. E. Belikov, M. A. Fomin, I. V. Gribkova, V. I. Shvets, S. D. Varfolomeev, Biochemistry (Moscow) Supplement Series A: Membrane and Cell Biology, 2011, 5, 227.
RF Pat. No. 2088229; Byul. Izobret. [Invent. Bull.], 1997, No. 24 (in Russian).
J. Wei, Y. Liu, S. Wang, J. Mol. Model., 2009, 15, 1185.
J. Hanson, J. M. Dogne, J. Ghiotto, A. L. Mordy, B. T. Kinsella, B. Pirotte, J. Med. Chem., 2007, 50, 3928.
E. Belgorede, R. Bossio, F. De Sio, S. Marcaccini, R. Perino, Heterocycles, 1983, 20, 501.
RF Pat. No. 2565754; Byul. Izobret. [Invent. Bull.], 2015, No. 29 (in Russian).
Platelets, 2nd ed., Ed. A. D. Michelson, 2007, Academic Press, Elsevier, Amsterdam–New York–London, 1334 p.
Author information
Authors and Affiliations
Corresponding author
Additional information
Based on the materials of the III Interdisciplinary Symposium on Medicinal, Organic, and Biological Chemistry and Pharmaceutics (MOBI-ChemPharma-2017; May 28—31, 2017; Sevastopol, Russia).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 0866–0877, May, 2018.
Rights and permissions
About this article
Cite this article
Demina, O.V., Belikov, N.E., Varfolomeev, S.D. et al. 3-Pyridylisoxazoles as prototypes of antiaggregatory agents. Russ Chem Bull 67, 866–877 (2018). https://doi.org/10.1007/s11172-018-2151-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-018-2151-2