Abstract
New potential biologically active derivatives, in which the sterically hindered pyrocatechol moiety is linked through a 2-thioacetyl covalent bridge to a number of secondary amines, pharmacophore γ-aminobutyric acid, and 2-amino-4-dimethylamino-1,3,5-triazine, were synthesized. The structures of most of the synthesized compounds were studied by X-ray diffraction.
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V. K. Promonenkov, K. I. Kobrakov, M.-G. A. Shvehgeimer, V. A. Rudenko, M. V. Shimanskaya, L. Ya. Leitis, Sredstva zashchity rasteniy na osnove galogenpiridinov [Plant Protection Agents Based on Halopyridines], in Itogi nauki i tekhniki. Ser. Organicheskaya khimiya [Results of Science and Technology. Ser. Organic Chemistry], Volume 16, ed. M. I. Kabachnik, Moscow, VINITI, 1990, p. 314 (in Russian).
V. D. Strelkov, L. V. Dyadyuchenko, I. G. Dmitrieva, Sintez novykh gerbitsidnykh antidotov dlya podsolnechnika [Synthesis of New Herbicide Antidotes for Sunflower], Krasnodar, Prosveshchenie-Yug, 2014, p. 53 (in Russian).
V. V. Zakharychev, A. V. Kuzenkov, A. M. Martsynkevich, Chem. Heterocycl. Compd. (Engl. Transl.), 2020, 56, 1491.
E. V. Babaev, Rev. J. Chem. (Engl. Transl.), 2011, 1, 161.
E. V. Babaev, Chem. Heterocycl. Compd. (Engl. Transl.), 2016, 52, 666.
J. M. Blackburn, J. L. Roizen, Asian J. Org. Chem., 2019, 8, 920.
K. Undheim, T. Benneche, Adv. Heterocycl. Chem., 1995, 62, 305.
V. V. Dotsenko, D. S. Buryi, D. Yu. Lukina, S. G. Krivokolysko, Russ. Chem. Bull., 2020, 69, 1829.
M. A. Bastrakov, A. K. Fedorenko, A. M. Starosotnikov, Russ. Chem. Bull., 2020, 69, 394.
M. A. Bastrakov, A. M. Starosotnikov, I. V. Fedyanin, I. L. Dalinger, Chem. Heterocycl. Compd. (Engl. Transl.), 2021, 57, 95.
Y. G. Shtyrlin, A. S. Petukhov, A. D. Strelnik, N. V. Shtyrlin, A. G. Iksanova, M. V. Pugachev, R. S. Pavelyev, M. S. Dzyurkevich, M. R. Garipov, K. V. Balakin, Russ. Chem. Bull., 2019, 68, 911.
F. Vuillermet, J. Bourret, G. Pelletier, J. Org. Chem., 2021, 86, 388.
V. P. Litvinov, V. V. Dotsenko, S. G. Krivokolysko, Russ. Chem. Bull., 2005, 54, 864.
E. A.-G. Bakhite, Phosphorus, Sulfur, Silicon, Relat. Elem., 2003, 178, 929.
V. P. Litvinov, V. V. Dotsenko, S. G. Krivokolysko, Adv. Heterocycl. Chem., 2007, 93, 117.
O. V. Ershov, M. A. Shishlikova, M. Yu. Ievlev, M. Yu. Belikov, V. N. Maksimova, Tetrahedron, 2019, 75, 130465.
M. A. Gouda, J. Heterocycl. Chem., 2011, 48, 1.
C. R. Hardy, Adv. Heterocycl. Chem., 1984, 36, 343.
V. P. Litvinov, Russ. Chem. Rev., 2004, 73, 637.
E. V. Babaev, V. L. Alifanov, A. V. Efimov, Russ. Chem. Bull., 2008, 57, 845.
N. M. Tverdokhleb, G. E. Khoroshilov, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 56.
D. A. Ponomarenko, G. E. Khoroshilov, D. A. Krasnikov, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 560.
N. M. Tverdokhleb, G. E. Khoroshilov, V. V. Dotsenko, Tetrahedron Lett., 2014, 55, 6593.
G. E. Khoroshilov, N. M. Tverdokhleb, V. S. Brovarets, E. V. Babaev, Tetrahedron, 2013, 69, 4353.
N. M. Tverdokhleb, G. E. Khoroshilov, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 1141.
N. M. Tverdokhleb, G. E. Khoroshilov, R. I. Zubatyuk, O. V. Shishkin, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 720.
G. Khoroshilov, I. Demchak, T. Saraeva, Synthesis, 2008, 1541.
G. E. Khoroshilov, T. A. Saraeva, K. Yu. Kuznetsov, Chem. Heterocycl. Compd. (Engl. Transl.), 2008, 44, 895.
O. V. Ershov, I. N. Bardasov, Chem. Heterocycl. Compd. (Engl. Transl.), 2017, 53, 1178.
V. V. Dotsenko, S. G. Krivokolysko, A. M. Semenova, Chem. Heterocycl. Compd. (Engl. Transl.), 2018, 54, 989.
V. P. Litvinov, S. V. Roman, V. D. Dyachenko, Russ. Chem. Rev., 2000, 69, 201.
V. P. Litvinov, Khimiya naftiridinov [Chemistry of Naphthyridines], Moscow, Ekonomika, 2008, p. 88 (in Russian).
Pat. PPR 145164; RZhKhim. [Chem. Ref. J.], 1989, 24 N 316 P (in Russian).
Pat. PPR 139253; RZhKhim. [Chem. Ref. J.], 1988, 12 N 174 P (in Russian).
W. A. Bolhofer, A. A. Deana, C. N. Habecker, J. M. Hoffman, N. P. Gould, A. M. Pietruszkiewicz, J. D. Prugh, M. L. Torchiana, E. J. Cragoe, Jr., R. Hirschmann, J. Med. Chem., 1983, 26, 538.
R. Skowroński, W. Strzyźewski, Pol. J. Chem., 1991, 65, 883.
Pat. PPR 139447; RZhKhim. [Chem. Ref. J.], 1988, 16 N 198 P (in Russian).
I. G. Dmitrieva, L. V. Dyadyuchenko, E. A. Kaigorodova, Izv. vuzov. Khimiya i khim. tekhnol. [Izv. Higher Inst. Chemistry and Chem. Technol.], 2005, 48, No. 12, 29 (in Russian).
I. G. Dmitrieva, L. V. Dyadyuchenko, L. D. Konyushkin, E. A. Kaigorodova, Izv. vuzov. Khimiya i khim. tekhnol. [Izv. Higher Inst. Chemistry and Chem. Technol.], 2006, 49, No. 8, 119 (in Russian).
L. V. Dyadyuchenko, I. G. Dmitrieva, N. A. Aksenov, V. V. Dotsenko, Chem. Heterocycl. Compd. (Engl. Transl.), 2018, 54, 964.
I. G. Dmitrieva, L. V. Dyadyuchenko, V. D. Strelkov, E. A. Kaigorodova, Chem. Heterocycl. Compd. (Engl. Transl.), 2009, 45, 1047.
L. V. Dyadyuchenko, I. G. Dmitrieva, D. Yu. Nazarenko, V. D. Strelkov, Chem. Heterocycl. Compd. (Engl. Transl.), 2014, 50, 1259.
V. V. Dotsenko, A. I. Ismiev, A. N. Khrustaleva, K. A. Frolov, S. G. Krivokolysko, E. A. Chigorina, A. P. Snizhko, V. M. Gromenko, I. S. Bushmarinov, R. K. Askerov, T. M. Pekhtereva, S. Yu. Suykov, E. S. Papayanina, A. V. Mazepa, A. M. Magerramov, Chem. Heterocycl. Compd. (Engl. Transl.), 2016, 52, 473.
V. V. Dotsenko, S. G. Krivokolysko, A. N. Chernega, V. P. Litvinov, Russ. Chem. Bull., 2003, 52, 969.
V. V. Dotsenko, E. A. Chigorina, S. G. Krivokolysko, Chem. Heterocycl. Compd. (Engl. Transl.), 2017, 53, 626.
A. M. Semenova, R. V. Oganesyan, V. V. Dotsenko, E. A. Chigorina, N. A. Aksenov, I. V. Aksenova, E. E. Netreba, Russ. J. Gen. Chem., 2019, 89, 19.
V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, A. N. Chernega, Chem. Heterocycl. Compd. (Engl. Transl.), 2007, 43, 599.
V. V. Dotsenko, K. A. Frolov, E. A. Chigorina, A. N. Khrustaleva, E. Yu. Bibik, S. G. Krivokolysko, Russ. Chem. Bull., 2019, 68, 691.
V. V. Dotsenko, A. N. Khrustaleva, K. A. Frolov, N. A. Aksenov, I. V. Aksenova, S. G. Krivokolysko, Russ. J. Gen. Chem., 2021, 91, 44.
A. I. Ismiyev, V. V. Dotsenko, N. A. Aksenov, I. V. Aksenova, A. M. Magerramov, Russ. Chem. Bull., 2020, 69, 1938.
V. V. Dotsenko, S. G. Krivokolysko, E. A. Chigorina, Russ. J. Gen. Chem., 2020, 90, 590.
V. V. Dotsenko, V. A. Dushenko, N. A. Aksenov, I. V. Aksenova, E. E. Netreba, Russ. J. Gen. Chem., 2019, 89, 1752.
E. A. Chigorina, A. V. Bespalov, V. V. Dotsenko, Russ. J. Gen. Chem., 2019, 89, 2018.
V. V. Dotsenko, D. S. Buryi, D. Yu. Lukina, A. N. Stolyarova, N. A. Aksenov, I. V. Aksenova, V. D. Strelkov, L. V. Dyadyuchenko, Monatsh. Chem., 2019, 150, 1973.
A. I. Ismiev, V. V. Dotsenko, N. A. Aksenov, G. Z. Mamedova, A. M. Magerramov, Russ. J. Gen. Chem., 2018, 88, 1533.
L. V. Dyadyuchenko, V. D. Strelkov, S. N. Mikhailichenko, V. N. Zaplishny, Chem. Heterocycl. Compd. (Engl. Transl.), 2004, 40, 308.
M. Mittelbach, Monatsh. Chem., 1985, 116, 689.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1368–1376, July, 2021.
The study was financially supported by the Ministry of Science and Higher Education of the Russian Federation (state assignment 0852-2020-0031 in the field of scientific research of the Southern Federal University, project No. FENW-2020-0031) using facilities of the Center of Collective Use of the Southern Federal University.
This paper does not contain descriptions of studies on animals or humans.
The authors declare no competing interests.
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Ukhin, L.Y., Kuz’mina, L.G., Alexeenko, D.V. et al. Synthesis, structure, and properties of 2-[(4,6-di-tert-butyl-2,3-dihydroxyphenyl)thio]acetic acid amides. Russ Chem Bull 70, 1368–1376 (2021). https://doi.org/10.1007/s11172-021-3225-0
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DOI: https://doi.org/10.1007/s11172-021-3225-0