СИНТЕЗ 4-АМІНО-1-АРИЛПІРАЗОЛІВ НА ОСНОВІ ЕТИЛ 2‑ЦІАНО‑2‑(2‑АРИЛГІДРАЗИНІЛІДЕН)АЦЕТАТІВ
Анотація
Описано метод отримання низки нових 3,5-дизаміщених 4-аміно-1‑арилпіразолів. Показано, що взаємодія етил 2-ціано-2-(2-арилгідразиніліден) ацетатів з галогенокетонами відбувається за наявності основи в умовах реакції Дікмана-Торпа. Етил 2-ціано-2-(2-арилгідразиніліден)ацетати одержано реакцією азосполучення під час взаємодії арилдіазонієвих солей з етил 2‑ціаноацетатом.
Ключові слова: 4-амінопіразоли, арендіазонію хлориди, реакція азосполучення, реакція Торпа-Циглера.
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Malvar D. do C., Ferreira R. T., de Castro R. A., de Castro L. L., Freitas A. C. et al. Antinociceptive, anti-inflammatory and antipyretic effects of 1.5-diphenyl-1H-Pyrazole-3-carbohydrazide, a new heterocyclic pyrazole derivative // Life sci. 2014. Vol. 95, No. 2. P. 81–88. DOI: https://doi.org/10.1016/j.lfs.2013.12.005
Taher A. T., Mostafa Sarg M. T., El-Sayed Ali N. R., Hilmy Elnagdi N. Design, Synthesis, Modeling Studies and Biological Screening of Novel Pyrazole Derivatives as Potential Analgesic and Anti-inflammatory Agents // Bioorg. Chem. 2019. Vol. 89. P. 103023. DOI: https://doi.org/10.1016/j.bioorg.2019.103023
Bekhit A. A., Nasralla S. N., El-Agroudy E. J., Hamouda N., El-Fattah A. A. et al. Investigation of the anti-inflammatory and analgesic activities of promising pyrazole derivative // Eur. J. Pharm. Sci. 2022. Vol.168. P. 106080. OI: https://doi.org/10.1016/j.ejps.2021.106080
Verma R., Verma S. K., Rakesh K. P., Girish Y. R., Ashrafizadeh M. et al. Pyrazole-based analogs as potential antibacterial agents against methicillin-resistance staphylococcus aureus (MRSA) and its SAR elucidation // Eur. J. Med. Chem. 2021. Vol. 212. P. 113134. DOI: https://doi.org/10.1016/j.ejmech.2020.113134
El Shehry M. F., Ghorab M. M., Abbas S. Y., Fayed E. A., Shedid S. A. et al. Quinoline derivatives bearing pyrazole moiety: Synthesis and biological evaluation as possible antibacterial and antifungal agents // Eur. J. Med. Chem. 2018. Vol. 143. P. 1463–1473. DOI: https://doi.org/10.1016/j.ejmech.2017.10.046
Yu B., Zhou S., Cao L., Hao Z., Yang D. et al. Design, Synthesis, and Evaluation of the Antifungal Activity of Novel Pyrazole-Thiazole Carboxamides as Succinate Dehydrogenase Inhibitors // J. Agric. Food Chem. 2020. Vol. 68. P. 7093–7102. DOI: https://doi.org/10.1021/acs.jafc.0c00062
Wang X., Wang A., Qiu L., Chen M., Lu A. et al. Expedient Discovery for Novel Antifungal Leads Targeting Succinate Dehydrogenase: Pyrazole-4-formylhydrazide Derivatives Bearing a Diphenyl Ether Fragment // J. Agric. Food. Chem. 2020. Vol. 68. P. 14426–14437. DOI: https://doi.org/10.1021/acs.jafc.0c03736
El-Naggar A. M., Hassan A., Elkaeed E. B., Alesawy M. S., Al-Karmalawy A. A. Design, synthesis, and SAR studies of novel 4-methoxyphenyl pyrazole and pyrimidine derivatives as potential dual tyrosine kinase inhibitors targeting both EGFR and VEGFR-2 // Bioorg. Chem. 2022. Vol. 123. P. 105770. DOI: https://doi.org/10.1016/j.bioorg.2022.105770
Yan W., Zhang L., Lv F., Moccia M., Carlomagno F. et al. Discovery of pyrazolo-thieno[3,2-d]pyrimidinylamino-phenyl acetamides as type-II pan-tropomyosin receptor kinase (TRK) inhibitors: Design, synthesis, and biological evaluation // Eur. J. Med. Chem. 2021. Vol. 216. P. 113265. DOI: https://doi.org/10.1016/j.ejmech.2021.113265
Achary R., Mathi G. R., Lee D. H., Yun C. S., Lee C. O. et al. Novel 2,4-diaminopyrimidines bearing fused tricyclic ring moiety for anaplastic lymphoma kinase (ALK) inhibitor. Bioorg. Med. Chem. Lett. 2017. Vol. 27. P. 2185–2191. DOI: https://doi.org/10.1016/j.bmcl.2017.03.073
Rai G., Brimacombe K. R., Mott B. T., Urban D. J., Hu X. et al. Discovery and Optimization of Potent, Cell-Active Pyrazole-Based Inhibitors of Lactate Dehydrogenase (LDH) // J. Med. Chem. 2017. Vol. 60. P. 9184–9204. DOI: https://doi.org/10.1021/acs.jmedchem.7b00941
Joshi G., Sharma M., Kalra S., Gavande N. S., Singh S., Kumar R. Design, synthesis, biological evaluation of 3,5-diaryl-4,5-dihydro-1H-pyrazole carbaldehydes as non-purine xanthine oxidase inhibitors: Tracing the anticancer mechanism via xanthine oxidase inhibition // Bioorg. Chem. 2021. Bioorg. Chem. 2022. Vol. 107. P. 104620. DOI: 10.1016/j.bioorg.2020.104620
Mousavi S., Zare S., Mirzaei M., Feizi A. Novel Drug Design for Treatment of COVID-19: A Systematic Review of Preclinical Studies // Can. J. Infect. Dis. Med. Microbiol. 2022. Vol. 2022. P. 2044282. DOI: https://doi.org/10.1155/2022/2044282
Khan M. F., Alam M. M., Verma G., Akhtar W., Akhter M., Shaquiquzzaman M. The therapeutic voyage of pyrazole and its analogs: A review // Eur. J. Med. Chem. 2016. Vol. 120. P. 170–201. DOI: https://doi.org/10.1016/j.ejmech.2016.04.077
15. Wang C.-R., Wang Z.-F., Shi L., Wang Z.-C., Zhu H.-L. Design, synthesis, and biological evaluation of pyrazole derivatives containing acetamide bond as potential BRAFV600E inhibitors // Bioorg. Med. Chem. Lett. 2018. Vol. 28(14). P. 2382–2390. DOI: https://doi.org/10.1016/j.bmcl.2018.06.028
Strohecker D. J., Lynch V. M., Holliday B. J., Jones R. A. Synthesis and electronic investigation of mono- and di-substituted 4-nitro- and 4-amino-pyrazol-1-yl bis(pyrazol-1-yl)pyridine-type ligands and luminescent Eu(III) derivatives // Dalton Trans. 2017. Vol. 46(24). P. 7733–7742. DOI: https://doi.org/10.1039/C7DT01153A
Corre L. L., Dasso Lang M. C., Garbay C., Gravier-Pelletier C. et al. Synthesis of Multifunctionalized 2-Iminothiazolidin-4-ones and Their 2-Arylimino Derivatives // Synthesis. 2016. Vol. 48. P. 4569–4579. DOI: http://dx.doi.org/10.1055/s-0035-1562521
Babu S. S., Muthuraja P., Yadav P., Gopinath P. Aryldiazonium Salts in Photoredox Catalysis – Recent Trends // Adv. Synth. Catal. 2021. Vol. 363. P. 1782–1809. DOI: https://doi.org/10.1002/adsc.202100136
Batsyts S., Shehedyn M., Goreshnik E. A., Obushak M. D., Schmidt A., Ostapiuk Y. V. 2-Bromo-2-chloro-3-arylpropanenitriles as C-3 Synthons for the Synthesis of Functionalized 3-Aminothiophenes // Eur. J. Org. Chem. 2019. Vol. 48. 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. DOI: https://doi.org/10.1055/s-0040-1719849
Bazel Y., Sidey V., Fizer M., Fedyshyn O., Vojteková V., Reiffová K., Ostapiuk Y., Tymoshuk O. Palladium determination with a new dye PNBTAN: Structural, UV-VIS, and DFT study // J. Mol. Struct. 2021. Vol. 1246. P. 131150. DOI: https://doi.org/10.1016/j.molstruc.2021.131150
Fedyshyn O., Bazel Y., Fizer M., Sidey V., Imrich J. et al. Spectroscopic and computational study of a new thiazolylazonaphthol dye 1-[(5-(3-nitrobenzyl)-1,3-thiazol-2-yl)diazenyl]naphthalen-2-ol // J. Mol. Liquids. 2020. Vol. 304. P. 112713. DOI: https://doi.org/10.1016/j.molliq.2020.112713
Kravets M., Shehedyn M., Ostapiuk Y. Synthesis of 5-aryl-1H-pyrazol-3-amines // Visnyk Lviv Univ. Ser. Chem. 2017. Vol. 58. P. 270–274.
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. P. 4575–4579. DOI: https://doi.org/10.1021/acs.orglett.2c01677
Finiuk N., Ostapiuk Y., Hreniukh V., Shalai Y., Matiychuk V. et al. Evaluation of antiproliferative activity of pyrazolothiazolopyrimidine derivatives.s // Ukr. Biochem. J. 2018. Vol. 90. P. 25–32. DOI: https://doi.org/10.15407/ubj90.02.025
Rydchuk P., Мarchyshyn М., Shevchuk L., Barabash O., Ostapiuk Yu. Spectrophotometry of 1-(1-methyl-1Н-pyrazol-3-il-azo)-naphtalen-2-ol // Visnyk Lviv Univ. Ser. Chem. 2020. Vol. 61. P. 189–197. DOI: http://dx.doi.org/10.30970/vch.6101.189
Singh U. P., Bhat H. R., Verma A., Kumawat M. K., Kaur R. et al. Phenyl hydrazone bearing pyrazole and pyrimidine scaffolds: design and discovery of a novel class of non-nucleoside reverse transcriptase inhibitors (NNRTIs) against HIV-1 and their antibacterial properties // RSC Adv. 2013. Vol. 3. P. 17335–17348. DOI: https://doi.org/10.1039/C3RA41604F
Ismail M. M. F., Abdulwahab H. G., Elnagdi M. H. Design, synthesis, and in vitro anticancer screening of novel pyrazolinyl-pyrazole/1, 2, 3-triazole hybrids // Heterocycl J. Chem. 2020. Vol. 57. P. 3584–3596. DOI: https://doi.org/10.1002/jhet.4076
DOI: http://dx.doi.org/10.30970/vch.6501.205
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