СИНТЕЗ 5-ЗАМІЩЕНИХ 2-АМІНОСЕЛЕНАЗОЛІВ НА ОСНОВІ ПРОДУКТІВ ХЛОРАРИЛЮВАННЯ АКРОЛЕЇНУ

M. Ostapiuk, O. Barabash, M. Obushak, Yu. Ostapiuk


DOI: http://dx.doi.org/10.30970/vch.6701.139

Анотація


Описано метод отримання нових 2-аміно-5-(R-бензил)селеназолів хлорарилюванням акролеїну з подальшою циклізацією із селеносечовиною. Показано, що реакцію хлорарилювання акролеїну та взаємодію отриманих 3-арил-2-хлорпропаналів з селеносечовиною можна проводити як двостадійним синтезом, так і за однореакторною методикою.

 

Ключові слова: 2-аміноселеназоли, арендіазоній хлориди, реакція Меєрвейна.

Повний текст:

PDF

Посилання


Longtin R. A forgotten debate: Is selenocysteine the 21st amino acid? // J. Nat. Cancer Inst. 2004. Vol. 96. P. 504–505. DOI: https://doi.org/10.1093/jnci/96.7.504

Iwaoka M., Arai K. From sulfur to selenium. A new research arena in chemical biology and biological chemistry // Curr. Chem. Biol. 2013. Vol. 7. P. 2–24. DOI: https://doi.org/10.2174/2212796811307010002

Gandhil U. H., Nagaraja T. P., Prabhu K. S. Selenoproteins and their role in oxidative stress and inflammation // Curr. Chem. Biol. 2013. Vol. 7. P. 65–73. DOI: https://doi.org/10.2174/2212796811307010007

Refaay D. A., Ahmed D. M., Mowafy A. M., Shaaban S. Evaluation of novel multifunctional organoselenium compounds as potential cholinesterase inhibitors against Alzheimer’s disease // Med. Chem. Res. 2022. Vol. 31. P. 894–904. DOI: https://doi.org/10.1007/s00044-022-02879-x

Mamgain R., Kostic M., Singh F. V. Synthesis and antioxidant properties of organoselenium compounds // Curr. Med. Chem. 2023. Vol. 30. P. 2421–2448. DOI: https://doi.org/10.2174/0929867329666220801165849

Qiao J., Zhao C., Liu J., Du Y. Design and synthesis of selenazole-substituted ritonavir analogs // Bioorg. Med. Chem. Lett. 2018. Vol. 28. P. 2379–2381. DOI: https://doi.org/10.1016/j.bmcl.2018.06.027

Eibergen N. R., Im I., Patel N. Y., Hergenrother P. J. Identification of a novel protein synthesis inhibitor active against gram-positive bacteria // ChemBioChem. 2012. Vol. 13. P. 574–583. DOI: https://doi.org/10.1002/cbic.201100727

Marković S. B., Maciejewska N., Olszewski M. еt al. Study of the anticancer potential of Cd complexes of selenazoyl-hydrazones and their sulfur isosters // Eur. J. Med. Chem. 2022. Vol. 238. Art. 114449. DOI: https://doi.org/10.1016/j.ejmech.2022.114449

Wu T.-Y., Chen X.-C., Tang G.-X. et al. Development and characterization of benzoselenazole derivatives as potent and selective c-MYC transcription inhibitors // J. Med. Chem. 2023. Vol. 66. P. 5484–5499. DOI: https://doi.org/10.1021/acs.jmedchem.2c01808

Araškov J. B., Nikolić M., Armaković S. et al. Structural, antioxidant, antiproliferative and in-silico study of pyridine-based hydrazonyl–selenazoles and their sulphur isosteres // J. Mol. Struct. 2021. Vol. 1240. Art. 130512. DOI: https://doi.org/10.1016/j.molstruc.2021.130512

Al-Tamimi A.-M. S., Etxebeste-Mitxeltorena M., Sanmartín C. et al. Discovery of new organoselenium compounds as antileishmanial agents // Bioorg. Chem. 2019 Vol. 86. P. 339–345. DOI: https://doi.org/10.1016/j.bioorg.2019.01.069

Wang H., Yue Y., Zhao H. et al. Neuroprotective effects of 2-substituted 1,3-selenazole amide derivatives on amyloid-beta-induced toxicity in a transgenic caenorhabditis elegans model of Alzheimer’s disease // Neurotoxic. Res. 2021. Vol. 39. P. 841–850. DOI: https://doi.org/10.1007/s12640-020-00321-x

Šmelcerović A., Tomović K., Šmelcerović Ž. et al. Xanthine oxidase inhibitors beyond allopurinol and febuxostat; an overview and selection of potential leads based on in silico calculated physico-chemical properties, predicted pharmacokinetics and toxicity // Eur. J. Med. Chem. 2017. Vol. 135. P. 491–516. DOI: https://doi.org/10.1016/j.ejmech.2017.04.031

Jain V. K., Priyadarsini K. I. Selenium compounds as promising antiviral agents // New J. Chem. 2024. Vol. 48. P. 6534–6552. DOI: https://doi.org/10.1039/D3NJ05180C

Leyssen P., Van Lommel A., Drosten C. et al. A novel model for the study of the therapy of Flavivirus infections using the Modoc virus // Virology. 2001. Vol. 279. P. 27–37. DOI: https://doi.org/10.1006/viro.2000.0723

Paragas J., Whitehouse C. A., Endy T. P., Bray M. A simple assay for determining antiviral activity against Crimean-Congo hemorrhagic fever virus // Antivir. Res. 2004. Vol. 62. P. 21–25. DOI: https://doi.org/10.1016/j.antiviral.2003.11.006

Chung D.-H., Sun Y., Parker W. B. et al. Ribavirin reveals a lethal threshold of allowable mutation frequency for Hantaan virus // J. Virol. 2007. Vol. 81. P. 11722–11729. DOI:https://doi.org/10.1128/JVI.00874-07

Roth J. P., Li J. K.-K., Smee D. F. et al. A recombinant, infectious human parainfluenza virus type 3 expressing the enhanced green fluorescent protein for use in high-throughput antiviral assays // Antivir. Res. 2009. Vol. 82. P. 12–21. DOI: https://doi.org/10.1016/j.antiviral.2009.01.001

Dzedulionytė K., Voznikaitė P., Bieliauskas A. et al. Methyl 2-Amino-4-[1-(tert-butoxycarbonyl)azetidin-3-yl]-1,3-selenazole-5-carboxylate // Molbank 2021. No.2. M1207. DOI: https://doi.org/10.3390/M1207

Schwartz Radatz C., Lange Coelho F., Sangiogo Gil E. et al. Ground and excited-state properties of 1,3-benzoselenazole derivatives: A combined theoretical and experimental photophysical investigation // J. Mol. Struc. 2020. Vol. 1207. Art. 127817. DOI: https://doi.org/10.1016/j.molstruc.2020.127817

Nishina A., Sekiguchi A., Fukumoto R.-H., Koketsu M. et al. Selenazoles (selenium compounds) facilitate survival of cultured rat pheochromocytoma PC12 cells after serum-deprivation and stimulate their neuronal differentiation via activation of Akt and mitogen-activated protein kinase, respectively // Biochem. Biophys. Res. Commun. 2007. Vol. 352. P. 360–365. DOI: https://doi.org/10.1016/j.bbrc.2006.11.025

Poerschke R. L., Moos P. J. Thioredoxin reductase 1 knockdown enhances selenazolidine cytotoxicity in human lung cancer cells via mitochondrial dysfunction // Biochem. Pharmacol. 2011. Vol. 81. P. 211–221. DOI: https://doi.org/10.1016/j.bcp.2010.09.024

Angeli A., Trallori E., Ferraroni M., Di Cesare Mannelli L. et al. Discovery of new 2, 5-disubstituted 1,3-selenazoles as selective human carbonic anhydrase IX inhibitors with potent anti-tumor activity // Eur. J. Med. Chem. 2018. Vol. 157. P. 1214–1222. DOI: https://doi.org/10.1016/j.ejmech.2018.08.096

Laczkowski K., Misiura K., Biernasiuk A., Malm A. Discovery and Evaluation of Efficient Selenazoles with High Antifungal Activity Against Candida spp. Med. Chem. 2015. Vol. 11. P. 118–127.

Laczkowski K. Z., Biernasiuk A., Baranowska-Laczkowsky A., Zielinska S. et al. Synthesis, antimicrobial and anticonvulsant screening of small library of tetrahydro-2H-thiopyran-4-yl based thiazoles and selenazoles // J. Enzym. Inhib. Med. Chem. 2016. Vol. 31. P. 24–39. DOI: https://doi.org/10.1080/14756366.2016.1186020

Kuchar J., Reinhold K., Rösgen V., Nöthling N. et al. Synthesis, Reactivity and Antimicrobial Activity of a Series of 2-Arylamino-1,3-selenazoles // Molecules 2021. Vol. 26. 7695. DOI: https://doi.org/10.3390/molecules26247695

Vahter J., Viht K., Uri A., Manoharan G. B. et al. Thiazole- and selenazole-comprising high-affinity inhibitors possess bright microsecond-scale photoluminescence in complex with protein kinase CK2 // Bioorg. Med. Chem. 2018. Vol. 26. P. 5062–5068. DOI: https://doi.org/10.1016/j.bmc.2018.09.003

Malinauskienė V., Kveselytė A., Dzedulionytė K., Bieliauskas A. et al. L-Proline and related chiral heterocyclic amino acids as scaffolds for the synthesis of functionalized 2-amino-1,3-selenazole-5-carboxylates // Chem. Heterocycl. Comp. 2018. Vol. 54. P. 469–473. DOI: https://doi.org/10.1007/s10593-018-2291-1

Liu H.-W., Fang Y., Wang S.-Y., Ji S.-J. Base-Promoted Multicomponent Reactions: A Synthesis of 2-Amino-1,3-selenazole Derivatives // J. Org. Chem. 2020. Vol. 85. P. 3508–3516. DOI: https://doi.org/10.1021/acs.joc.9b03234

Hassell-Hart S., Speranzini E., Srikwanjai S., Hossack E. et al. Synthesis of a Thiazole Library via an Iridium-Catalyzed Sulfur Ylide Insertion Reaction // Org. Lett. 2022. Vol. 24(43). P. 7924–7927. DOI: https://doi.org/10.1021/acs.orglett.2c02996

Erian A. W., Sherif S. M., Gaber H. M. The Chemistry of α-Haloketones and Their Utility in Heterocyclic Synthesis // Molecules 2003. Vol. 8. P. 793–865. DOI: https://doi.org/10.3390/81100793

Pravst I., Zupan M., Stavber S. Halogenation of ketones with N-halosuccinimides under solvent-free reaction conditions // Tetrahedron 2008. Vol. 64. P. 5191–5199. DOI: https://doi.org/10.1016/j.tet.2008.03.048

Meerwein H., Buchner E., van Emster K. Über die Einwirkung aromatischer Diazoverbindungen auf α,β-ungesättigte Carbonylverbindungen // J. Prakt. Chem. 1939. Vol. 152. P. 237–266. DOI: https://doi.org/10.1002/prac.19391520705

Kindt S., Heinrich M. R. Recent Advances in Meerwein Arylation Chemistry // Synthesis. 2016. Vol. 48. P. 1597–1606. DOI: 10.1055/s-0035-1561586

Mo F., Qiu D., Zhang L., Wang J. Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds // Chem. Rev. 2021. Vol. 121. P. 5741–5829. DOI: https://doi.org/10.1021/acs.chemrev.0c01030

Shukla C. A., Atapalkar R. S., Kulkarni A. A. Efficient Processing of Reactions Involving Diazonium Salts: Meerwein Arylation in an Impinging-Jet Reactor // Org. Process Res. Dev. 2020. Vol. 24. P. 1658–1664. DOI: https://doi.org/10.1021/acs.oprd.0c00271

Batsyts S., Shehedyn M., Goreshnik E. A., Obushak M. D. et al. 2-Bromo-2-chloro-3-arylpropanenitriles as C-3 Synthons for the Synthesis of Functionalized 3-Aminothiophenes // Eur. J. Org. Chem. 2019. Vol. 2019. P. 7842–7856. DOI: https://doi.org/10.1002/ejoc.201901512

Ostapiuk Y. V., Shehedyn M., Barabash O. V., Demydchuk B. et al. Bromoarylation of Methyl 2-Chloroacrylate under Meerwein Conditions for the Synthesis of Substituted 3-Hydroxythiophenes // Synthesis 2022. Vol. 54. P. 732–740.

Ostapiuk Y. V., Shehedyn M., Barabash O. V., Demydchuk B. et al. One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones // Synthesis 2022. Vol. 54(16). P. 3658–3666. DOI: 10.1055/s-0041-1738070

Ostapiuk Y. V., Barabash O. V., Ostapiuk M. Y., Kravets M. et al.2-(Methoxycarbonyl)thiophen-3-yl-diazonium Salts: Efficient Precursors for the Formation of C–C Bonds in Thiophene-Containing Heterocyclic Systems // Molecules. 2025. Vol. 30(18). Art. 3758. DOI: https://doi.org/10.3390/molecules30183758

Ostapiuk Y. V., Barabash O. V., Ostapiuk M. Y., Goreshnik E. et al. Thiocyanatoarylation of methyl vinyl ketone under Meerwein conditions for the synthesis of 2-aminothiazole-based heterocyclic systems // Org. Lett. 2022. Vol. 24(25). P. 4575–4579. DOI: https://doi.org/10.1021/acs.orglett.2c01677

Finiuk N., Klyuchivska O., Ivasechko I., Hreniukh V. et al. Proapoptotic effects of novel thiazole derivative on human glioma cells // Anti-Cancer Drugs. 2019. Vol. 30. P. 27–37.


Посилання

  • Поки немає зовнішніх посилань.