The synthesis of new unsymmetrically substituted 1,4-dihydroisonicotinic acid bearing cyano and acetyl groups in positions 3 and 5 of the heterocycle has been developed. The methyl, ethoxycarbonylmethyl, and propionyloxymethyl esters of the acid have been obtained. The method of N-alkylation reaction of synthesized 1,4-dihydroisonicotinic acid esters has been elaborated.
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K. Bano, A. Ahmed, N. A. Ghafoor, A. Faiyaz, and N. Akhter, Pak. J. Biochem. Mol. Biol., 44, No. 3, 99 (2011), and references therein.
N. Edraki, A. R. Mehdipour, M. Khoshneviszadeh, and R. Miri, Drug Discovery Today, 14, 1058 (2009).
C. Safak and R. Simsek, Mini Rev. Med. Chem., 6, 747 (2006).
S. Goldmann and J. Stoltefuss, Angew. Chem., Int. Ed. Engl., 30, 1559 (1991).
A. Ashimori, T. Uchida, Y. Ohtaki, M. Tanaka, K. Ohe, C. Fukaya, M. Watanabe, M. Kagitani, and K. Yokoyama, Chem. Pharm. Bull., 39, 108 (1991).
Y. Tokuma and H. Noguchi, J. Chromatogr., A, 694, 181 (1995).
R. Peri, S. Padmanabhan, A. Rutledge, S. Singh, and D. J. Triggle, J. Med. Chem., 43, 2906 (2000).
S. Kongsamut, T. J. Kamp, R. J. Miller, and M. C. Sanguinetti, Biochem. Biophys. Res. Commun., 130, 141 (1985).
G. Franckowiak, M. Bechem, M. Schramm, and G. Thomas, Eur. J. Pharmacol., 114, 223 (1985).
A. Sobolev, M. C. R. Franssen, J. Poikans, G. Duburs, and A. Groot, Tetrahedron: Asymmetry, 13, 2389 (2002).
I. Stonans, I. Jansone, I. Jonane-Osa, E. Bisenieks, G. Duburs, I. Kalvins, B. Vigante, J. Uldrikis, I. Bruvere, L. Zuka, J. Poikans, and Z. Neidere, PCT Int. Appl., WO 2012010276; Chem. Abstr., 156, 230451 (2012).
I. Misane, G. Cebers, I. Liepa, M. Dambrova, S. Germane, V. Klusa, G. Duburs, and E. Bisenieks, Proc. Latv. Acad. Sci., Part B, № 5, 81 (1993).
M. N. Karpova, S. K. Germane, G. Tsebers, O. Y. Pankov, V. E. Klusha, G. Ya. Duburs, and E. A. Bisenieks, Bull. Exp. Biol. Med., 116, 1119 (1993).
I. Misane, V. Klusa, M. Dambrova, S. Germane, G. Duburs, E. Bisenieks, R. Rimondini, and S. O. Ögren, Eur. Neuropsychopharmacol., 8, 329 (1998).
M. A. S. Fernandes, M. S. Santos, J. A. F. Vicente, A. J. M. Moreno, A. Velena, G. Duburs, and C. R. Oliveira, Mitochondrion, 3, 47 (2003).
A. Velēna, A. Skujiņš, S. Svirskis, E. Bisenieks, J. Uldriķis, J. Poikāns, G. Duburs, and V. Kluša, Cell Biochem. Funct., 15, 211 (1997).
K. G. Watson, G. J. Bird, G. J. Farquharson, R. J. Conway, and P. G. Tucker, US Pat. Appl. 4631081; Chem. Abstr., 101, 110737 (1984).
F. Biellmann, H. J. Callot, and M. P. Goeldner, Tetrahedron, 26, 4655 (1970).
F. Biellmann and H. J. Callot, Tetrahedron, 26, 4799 (1970).
F. Biellmann and H. J. Callot, Tetrahedron, 26, 4809 (1970).
F. Biellmann and M. P. Goeldner, Tetrahedron, 27, 1789 (1971).
E. Sausin', V. K. Lusis, G. Ya. Dubur, and Yu. I. Beilis, Khim. Geterotsikl. Soedin., 1508 (1978). [Chem. Heterocycl. Compd., 14, 1226 (1978).]
A. Z. Zandersons, V. K. Lusis, D. Kh. Mutsenietse, and G. Ya. Dubur, Khim. Geterotsikl. Soedin., 81 (1987). [Chem. Heterocycl. Compd., 23, 66 (1987).]
S. Naveen, S. M. Anandalwar, J. S. Prasad, D. Manwar, A. Mishra, and A. Shah, J. Chem. Crystallogr., 38, 315 (2008).
G. Giorgi, M. F. A. Adamo, F. Ponticelli, and A. Ventura, Org. Biomol. Chem., 8, 5339 (2010).
S. Morales-Ríos, A. Martínez-Richa, Z. Hernándes-Gallegos, A. Hernándes-Barragán, R. Vera-Graziano, P. Joseph-Nathan, and Z. Naturforsch., 62b, 549 (2007).
R. S. Rathore, B. Palakshi Reddy, V. Vijayakumar, R. Venkat Ragavan, and T. Narasimhamurthy, Acta Crystallogr., Sect. B: Struct. Sci., B65, 375 (2009).
R. Fossheim, A. Joslyn, A. J. Solo, E. Luchowski, A. Rutledge, and D. J. Triggle, J. Med. Chem., 31, 300 (1988).
L. Fizer and M. Fizer, in: Reagents for Organic Synthesis [Russian translation], Vol. 1, Mir, Moscow (1970), p. 242.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 778–787, May, 2013.
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Goba, I., Turovska, B., Belyakov, S. et al. Synthesis of Novel Unsymmetrically Substituted 1,4-Dihydroisonicotinic Acid and its Derivatives. Chem Heterocycl Comp 49, 726–735 (2013). https://doi.org/10.1007/s10593-013-1304-3
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DOI: https://doi.org/10.1007/s10593-013-1304-3