vestichИзвестия Национальной академии наук Беларуси. Серия химических наукProceedings of the National Academy of Sciences of Belarus, Chemical Series1561-83312524-2342The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1561-8331-2024-60-2-145-152vestich-881Research ArticleОРГАНИЧЕСКАЯ ХИМИЯORGANIC CHEMISTRYСинтез N-арил- и пиридинзамещенных производных валина, лейцина и изолейцинаSynthesis of N-aryl and pyridine-substituted derivatives of valine, leucine and isoleucineАкишинаЕ. А.AkishinaЕ. А.

Акишина Екатерина Александровна – научный сотрудник

ул. Сурганова, 13, 220072, Минск

Akishina Ekaterina A. – Researcher

13, Surganov Str., 220072, Minsk

che.semenovaea@mail.ruКнижниковВ. А.KnizhnikovV. А.

Книжников Валерий Алексеевич – доктор химических наук

Knizhnikov Valeriy A. – D. Sc. (Chemistry)

ПоповаЛ. А.PopovaL. А.

Попова Людмила Александровна – старший научный сотрудник

ул. Сурганова, 13, 220072, Минск

Popova Ludmila A. – Senior Researcher

13, Surganov Str., 220072, Minsk

КаранкевичЕ. Г.KarankevichЕ. G.

Каранкевич Елена Григорьевна – кандидат химических наук, заведующий лабораторией

ул. Сурганова, 13, 220072, Минск

Karankevich Elena G. – Ph. D. (Chemistry), Head of the Laboratory

13, Surganov Str., 220072, Minsk

extract@ifoch.bas-net.byИнститут физико-органической химии Национальной академии наук БеларусиInstitute of Physical Organic Chemistry of the National Academy of Sciences of Belarus202424052024602145152Copyright © Акишина Е.А., Книжников В.А., Попова Л.А., Каранкевич Е.Г., 20242024Акишина Е.А., Книжников В.А., Попова Л.А., Каранкевич Е.Г.Akishina Е.А., Knizhnikov V.А., Popova L.А., Karankevich Е.G.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vestichem.belnauka.by/jour/article/view/881

Разработан препаративный метод синтеза N-арил- и пиридинзамещенных производных валина, лейцина, изолейцина посредством конденсации натриевых солей аминокислот с бензальдегидом, салициловым альдегидом, п-хлорбензальдегидом, 3-пиридинкарбальдегидом, ванилином и последующим восстановлением боргидридом натрия.

A preparative method for the synthesis of N-aryl- and pyridine-substituted valine, leucine, isoleucine derivatives by condensation of amino acids sodium salts with benzaldehyde, salicylaldehyde, vanillin, p-chlorobenzaldehyde, 3-pyridinecarbaldehyde and subsequent reduction with sodium borohydride has been developed.

валинлейцинизолейциноснования Шиффагидроксибензальдегиды3-пиридинкарбальдегидп-хлорбензальдегидvalineleucineisoleucineSchiff baseshydroxybenzaldehydes3-pyridinecarbaldehydep-chlorobenzaldehydeReferencesБизунок, Н. А. Фармакодинамические взаимодействия N-замещенных производных L-пролина и клеточных модуляторов разного типа действия на модели Fc-гамма-R-зависимого фагоцитоза / Н. А. Бизунок // Вес. Нац. акад. навук Беларусі. Сер. мед. навук. – 2012. – № 1. – С. 53–62.Bizunok N. A. Pharmacodynamic interactions of N-substituted derivatives of L-proline and cellular modulators of various types of action on the model of Fc-gamma-R-dependent phagocytosis. Vestsi Natsyyanal’nai akademii navuk Belarusi. Serуya medуtsуnskikh navuk = Proceedings of the National Academy of Sciences of Belarus. Medical series, 2012, no 1, pp. 53–62 (in Russian).The role of a Schiff base scaffold, N-(2-hydroxy acetophenone) glycinate-in overcoming multidrug resistance in cancer / A. Ganguly [et al.] // Eur. J. Pharm. Sci. – 2014. – Vol. 51. – P. 96–109. https://doi.org/10.1016/j.ejps.2013.09.003Ganguly A., Chakraborty P., Banerjee K., Choudhuri S. K. The role of a Schiff base scaffold, N-(2-hydroxy acetophenone) glycinate-in overcoming multidrug resistance in cancer. Eur. J. Pharm. Sci., 2014, vol. 51, pp. 96–109. https://doi.org/10.1016/j.ejps.2013.09.003Amino Acids in the Development of Prodrugs / N. Vale [et al.] // Molecules. – 2018. – Vol. 23, № 9. – P. 2318. https://doi.org/10.3390/molecules23092318Vale N., Ferreira A., Matos J., Fresco P., Gouveia M. J. Amino Acids in the Development of Prodrugs. Molecules, 2018, vol. 23, no. 9, pp. 2318. https://doi.org/10.3390/molecules23092318Al-Garawi, Z. S. M. Synthesis and Characterization of New Amino Acid-Schiff Bases and Studies their Effects on the Activity of ACP, PAP and NPA Enzymes (in vitro) / Z. S. M. Al-Garawi, I. H. R. Tomi, A. H. R. Al-Daraji // E-J. Chem. – 2012. – Vol. 9, № 2. – P. 962–969. https://doi.org/10.1155/2012/218675Al-Garawi Z. S. M., Tomi I. H. R., Al-Daraji A. H. R. Synthesis and Characterization of New Amino Acid-Schiff Bases and Studies their Effects on the Activity of ACP, PAP and NPA Enzymes (in vitro). E-Journal of Chemistry, 2012, vol. 9, no. 2, pp. 962–969. https://doi.org/10.1155/2012/218675Arunadevi, A. Biological response of Schiff base metal complexes incorporating amino acids – a short review / A. Arunadevi, N. Raman // J. Coord. Chem. – 2020. – Vol. 73, № 15. – P. 2095–2116. https://doi.org/10.1080/00958972.2020.1824293Arunadevi A., Raman N. Biological response of Schiff base metal complexes incorporating amino acids – a short review. Journal of Coordination Chemistry, 2020, vol. 73, no. 15, pp. 2095–2116. https://doi.org/10.1080/00958972.2020.1824293.NMR studies of solvent-assisted proton transfer in a biologically relevant Schiff base: Toward a distinction of geometric and equilibrium H-bond isotope effects / S. Sharif [et al.] // J. Am. Chem. Soc. – 2006. – Vol. 128, № 10. – P. 3375–3387. https://doi.org/10.1021/ja056251vSharif S., Denisov G. S., Toney M. D., Limbach H. H. NMR studies of solventassisted proton transfer in a biologically relevant Schiff base: Toward a distinction of geometric and equilibrium H-bond isotope effects. Journal of the American Chemical Society, 2006, vol. 128, no. 10, pp. 3375–3387. https://doi.org/10.1021/ja056251vБензоидно-хиноидная таутомерия азометинов и их структурных аналогов. LIII. Имины 5-гидрокси- и 5-гидрокси-6-нитро-2,3-дифенилбензо[b]фуран-4-карбальдегидов / Е. Н. Шепеленко [и др.] // ЖОрХ. – 2007. – Т. 43, № 4. – С. 561–565. https://doi.org/10.1134/S1070428007040124Shepelenko E. N., Tsukanov A. V., Revinskii Yu. V., Dubonosov A. D., Bren’ V. A., Minkin V. I. Benzoid-quinoid tautomerism of Schiff bases and their structural analogs: LIII. Schiff bases derived from 5-hydroxy- and 5-hydroxy-6- nitro-2,3-diphenyl-1-benzofuran-4-carbaldehydes. Russian Journal of Organic Chemistry, 2007, vol. 43, no. 4, pp. 559–563 (in Russian). https://doi.org/10.1134/S1070428007040124Synthesis, Identification and Antibacterial Activities of Amino Acid Schiff Base Cu(II) Complexes with Chlorinated Aromatic Moieties / N. Otani [et al.] // Appl. Microbiol. – 2022. – Vol. 2, № 2. – P. 438–448. https://doi.org/10.3390/applmicrobiol2020032.Otani N., Fayeulle A., Nakane D., Léonard E., Akitsu T. Synthesis, Identification and Antibacterial Activities of Amino Acid Schiff Base Cu(II) Complexes with Chlorinated Aromatic Moieties. Appl. Microbiol., 2022, vol. 2, no. 2, pp. 438-448. https://doi.org/10.3390/applmicrobiol2020032Saikumari, N. Synthesis and characterization of amino acid Schiff base and its copper (II) complex and its antimicrobial studies / N. Saikumari // Materials Today: Proceedings. – 2021. – Vol. 47, № 9. – P. 1777–1781. https://doi.org/10.1016/j.matpr.2021.02.607.Li L.–J., Wang C., Tian C.,Yang X.-Y., Hua X.-X., Du J.-L. Water-soluble platinum(II) complexes of reduced amino acid Schiff bases: synthesis, characterization, and antitumor activity. Research on Chemical Intermediates, 2012, vol. 39, no. 2, pp. 733–746. https://doi.org/10.1007/s11164-012-0593-ySynthesis of Amino Acid Schiff Base Nickel (II) Complexes as Potential Anticancer Drugs In Vitro / Y. Li [et al.] // Bioinorg. Chem. Appl. – 2020. – Vol. 2020. https://doi.org/10.1155/2020/8834859Pervaiz M., Ahmad I., Yousaf M., Kirn S., Munawar A., Saeed Z., Adnan A., Gulzar T., Kamal T., Ahmad A., Rashid A. Synthesis, spectral and antimicrobial studies of amino acid derivative Schiff base metal (Co, Mn, Cu, and Cd) complexes. Spectrochimica Acta, Part A, 2019, vol. 206, pp. 642–649. https://doi.org/10.1016/j.saa.2018.05.057Water-soluble platinum(II) complexes of reduced amino acid Schiff bases: synthesis, characterization, and antitumor activity / L.–j. Li [et al.] // Res. Chem. Intermed. – 2012. – Vol. 39, № 2. – P. 733–746. https://doi.org/10.1007/s11164-012-0593-yLi L.-J., Wang C., Tian C., Yang X.-Y., Hua X.-X., Du J.-L. Water-soluble platinum(II) complexes of reduced amino acid Schiff bases: synthesis, characterization, and antitumor activity. Res. Chem. Intermed., 2012, vol. 39, no. 2, pp. 733–746. https://doi.org/10.1007/s11164-012-0593-ySynthesis, spectral and antimicrobial studies of amino acid derivative Schiff base metal (Co, Mn, Cu, and Cd) complexes. / M. Pervaiz [et al.] // Spectrochim. Acta, Part A. – 2019. – Vol. 206. – P. 642–649. https://doi.org/10.1016/j.saa.2018.05.057Pervaiz M., Yousaf M., Ahmad I., Munawar A., Saeed Z., Adnan A., Gulzar T., Kirn S., Kamal T., Ahmad A. Synthesis, spectral and antimicrobial studies of amino acid derivative Schiff base metal (Co, Mn, Cu, and Cd) complexes. Spectrochim. Acta, Part A., 2019, vol. 206, pp. 642–649. https://doi.org/10.1016/j.saa.2018.05.057Schiff base and reductive amination reactions of α-amino acids: a facile route toward N-alkylated amino acids and peptoid synthesis / X. Fu [et al.] // Polym. Chem. – 2018. – Vol. 9. – P. 4617–4624. https://doi.org/10.1039/c8py00924dFu X., Li Z., Wei J., Sun J., Li Z. Schiff base and reductive amination reactions of α-amino acids: a facile route toward N-alkylated amino acids and peptoid synthesis. Polymer Chemistry, 2018, vol. 9, pp. 4617–4624. https://doi.org/10.1039/c8py00924dTernary copper(II) complexes with amino acid chains and heterocyclic bases: DNA binding, cytotoxic and cell apoptosis induction properties / T. Ma [et al.] // J. Inorg. Biochem. – 2015. – Vol. 144. – P. 38–46. https://doi.org/10.1016/j.jinorgbio.2014.12.011Ma T., Xu J., Wang Y., Yu H., Yang Y., Liu Y., Ding W., Zhu W., Chen R., Ge Zh., Tan Y., Jia L., Zhu T. Ternary copper(II) complexes with amino acid chains and heterocyclic bases: DNA binding, cytotoxic and cell apoptosis induction properties. Journal of Inorganic Biochemistry, 2015, vol. 144, pp. 38–46. https://doi.org/10.1016/j.jinorgbio.2014.12.011Книжников, В. А. Азометины на основе натриевых солей валина и лейцина / В. А. Книжников, О. П. Азизбекян, В. М. Прищепенко // ЖОрХ. – 2003. – Т. 73, № 9. – С. 1529–1531. https://doi.org/10.1023/B:RUGC.0000015996.53534.48Knizhnikov V. A., Azizbekyan O. P., Prishchepenko V. M. Azomethines on the basis of sodium salts of valine and leucine. Russian Journal of General Chemistry, 2003, vol. 73, no. 9, pp. 1445–1447 (in Russian). https://doi.org/10.1023/B:RUGC.0000015996.53534.48Discovery of Novel N-(4-Hydroxybenzyl)valine Hemoglobin Adducts in Human Blood / A. Degner [et al.] // Chem. Res. Toxicol. – 2018. – Vol. 31. – P. 1305–1314. https://doi.org/10.1021/acs.chemrestox.8b00173Degner A., Carlsson H., Karlsson I., Eriksson J., Pujari S. S., Tretyakova N. Y., Törnqvist M. Å. Discovery of Novel N-(4-Hydroxybenzyl)valine Hemoglobin Adducts in Human Blood. Chemical Research in Toxicology, 2018, vol. 31, pp. 1305–1314. https://doi.org/10.1021/acs.chemrestox.8b00173Resolution of RacemicN-Benzyl α-Amino Acids by Liquid-Liquid Extraction: A Practical Method Using a Lipophilic Chiral Cobalt(III) Salen Complex and Mechanistic Studies / P. Dzygiel [et al.] // Eur. J. Org. Chem. – 2008. – Vol. 2008, iss. 7. – P. 1253–1264. https://doi.org/10.1002/ejoc.200701101Dzygiel P., Reeve T. B., Piarulli U., Krupicka M., Tvaroska I., Gennari C. Resolution of RacemicN-Benzyl α-Amino Acids by Liquid-Liquid Extraction: A Practical Method Using a Lipophilic Chiral Cobalt(III) Salen Complex and Mechanistic Studies. European Journal of Organic Chemistry, 2008, vol. 2008, iss. 7, pp. 1253–1264. doi:10.1002/ejoc.200701101Dubey, M. Sodium and Potassium Ion Directed Self-Assembled Multinuclear Assembly of Divalent Nickel or Copper andl-Leucine Derived Ligand / M. Dubey, R. R. Koner, M. Ray // Inorg. Chem. – 2009. – Vol. 48, № 19. – P. 9294–9302. https://doi.org/10.1021/ic9011444Dubey M., Koner R. R., Ray M. Sodium and Potassium Ion Directed Self-Assembled Multinuclear Assembly of Divalent Nickel or Copper andl-Leucine Derived Ligand. Inorganic Chemistry, 2009, vol. 48, no. 19, pp. 9294–9302. https://doi.org/10.1021/ic9011444

The authors declare that there are no conflicts of interest present.