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Mendeleev Communications, 2021, Volume 31, Issue 1, Pages 42–45
DOI: https://doi.org/10.1016/j.mencom.2021.01.012
(Mi mendc828)
 

This article is cited in 16 scientific papers (total in 16 papers)

Communications

Design and synthesis of pyrazolo[3,4-d]pyridazine 5,6-dioxides as novel NO-donors

A. S. Kulikova, M. A. Epishinaa, E. S. Zhilina, A. D. Shuvaevab, L. L. Fershtata, N. N. Makhovaa

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation
Abstract: A simple and effective protocol for the synthesis of 2H-pyrazolo[3,4-d]pyridazine 5,6-dioxides includes a transformation of accessible 3,4-diacetyl-5-methyl-1H-pyrazoles into the corresponding 1,4-dioximes followed by their N2O4- mediated oxidative cyclization. All transformations proceed under mild conditions in good to high yields. According to the Griess assay, synthesized 2H-pyrazolo[3,4-d]pyridazine 5,6-dioxides showed promising NO-donor profiles producing NO in a wide range of concentrations.
Keywords: NO-donors, oxidative cyclization, pharmacologically oriented compounds, 1,2,5-oxadiazoles, pyrazolo[3,4-d]pyridazine 5,6-dioxides, dinitrogen tetraoxide.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (4.4 Mb)


Citation: A. S. Kulikov, M. A. Epishina, E. S. Zhilin, A. D. Shuvaev, L. L. Fershtat, N. N. Makhova, “Design and synthesis of pyrazolo[3,4-d]pyridazine 5,6-dioxides as novel NO-donors”, Mendeleev Commun., 31:1 (2021), 42–45
Linking options:
  • https://www.mathnet.ru/eng/mendc828
  • https://www.mathnet.ru/eng/mendc/v31/i1/p42
  • This publication is cited in the following 16 articles:
    1. Yuriy M. Markitanov, Sergiy A. Siry, Vadim M. Timoshenko, Sergiy S. Mykhaylychenko, Alexandr I. Khyzhan, Eduard B. Rusanov, Svitlana V. Shishkina, Yuriy G. Shermolovich, “Trifluoromethylated 2H‐Thiete, 2,3‐Dihydrothiophenes and 3,4‐Dihydro‐2H‐thiopyranes S,S‐Dioxides in [3+2]‐Cycloaddition Reactions with Diazo Compounds and Nitrilimines”, ChemistrySelect, 9:35 (2024)  crossref
    2. Yuri A Sidunets, Valeriya G Melekhina, Leonid L Fershtat, “Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system”, Beilstein J. Org. Chem., 20 (2024), 2342  crossref
    3. Dmitry B. Vinogradov, Leonid L. Fershtat, “Energetic azine N-oxides: State-of-the-art achievements in the synthesis and performance”, Chemical Engineering Journal, 2024, 158859  crossref
    4. Zeinab A. Abdallah, Ahmed M. Abdelfattah, Ahmed A. M. Ahmed, “Synthesis and Characterization of Benzo[6,7]Cyclohepta[1,2‐b]Pyrazolo[4,3‐e]Pyridines”, Journal of Heterocyclic Chem, 2024  crossref
    5. V. N. Charushin, E. V. Verbitskiy, O. N. Chupakhin, D. V. Vorobyeva, P. S. Gribanov, S. N. Osipov, A. V. Ivanov, S. V. Martynovskaya, E. F. Sagitova, V. D. Dyachenko, I. V. Dyachenko, S. G. Krivokolylsko, V. V. Dotsenko, A. V. Aksenov, D. A. Aksenov, N. A. Aksenov, A. A. Larin, L. L. Fershtat, V. M. Muzalevskiy, V. G. Nenajdenko, A. V. Gulevskaya, A. F. Pozharskii, E. A. Filatova, K. V. Belyaeva, B. A. Trofimov, I. A. Balova, N. A. Danilkina, A. I. Govdi, A. S. Tikhomirov, A. E. Shchekotikhin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, Yu. N. Klimochkin, M. V. Leonova, I. M. Tkachenko, V. A.-o. Mamedov, V. L. Mamedova, N. A. Zhukova, V. E. Semenov, O. G. Sinyashin, O. V. Borshchev, Yu. N. Luponosov, S. A. Ponomarenko, A. S. Fisyuk, A. S. Kostyuchenko, V. G. Ilkin, T. V. Beryozkina, V. A. Bakulev, A. S. Gazizov, A. A. Zagidullin, A. A. Karasik, M. E. Kukushkin, E. K. Beloglazkina, N. E. Golantsov, A. A. Festa, L. G. Voskresenskii, V. S. Moshkin, E. M. Buev, V. Ya. Sosnovskikh, I, “The chemistry of heterocycles in the 21st century”, Russian Chem. Reviews, 93:7 (2024), RCR5125  mathnet  mathnet  crossref  isi  scopus
    6. Alexander D. Shuvaev, Egor S. Zhilin, Leonid L. Fershtat, “NOBF4-Mediated Assembly of the Sydnone Imine Scaffold in the Synthesis of Double Nitric Oxide Donors”, Synthesis, 55:12 (2023), 1863  crossref
    7. Irina A. Stebletsova, Alexander A. Larin, Ivan V. Ananyev, Leonid L. Fershtat, “Regioselective Synthesis of NO-Donor (4-Nitro-1,2,3-triazolyl)furoxans via Eliminative Azide–Olefin Cycloaddition”, Molecules, 28:19 (2023), 6969  crossref
    8. Jing Zhang, Yanze Jiang, Xiaojie Cheng, Yingjie Xie, Jianfeng Zhao, Jiena Weng, “Recent advances in versatile pyridazine-cored materials: principles, applications, and challenges”, J. Mater. Chem. C, 11:17 (2023), 5563  crossref
    9. V. A. Sereda, L. L. Fershtat, “Divergent oriented synthesis of 2H-1,2,3-triazoles via rearrangement of furoxanylhydrazones”, Mendeleev Commun., 33:6 (2023), 764–766  mathnet  crossref
    10. Ahmed A. M. Ahmed, Ahmed E. M. Mekky, Sherif M. H. Sanad, “New piperazine-based bis(thieno[2,3-b]pyridine) and bis(pyrazolo[3,4-b]pyridine) hybrids linked to benzofuran units: Synthesis and in vitro screening of potential acetylcholinesterase inhibitors”, Synthetic Communications, 52:6 (2022), 912  crossref
    11. Kseniia Yu Titenkova, Alexander V. Shaferov, Alexander A. Larin, Margarita A. Epishina, Alexander S. Kulikov, Ivan V. Ananyev, Leonid L. Fershtat, “Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles”, Tetrahedron, 103 (2022), 132563  crossref
    12. Valentina A. Kobelevskaya, Ludmila I. Larina, Alexandr V. Popov, “A Regioselective Synthesis of 5-chloro-1-vinyl- and 3-alkenyl-5-chloro-1H-pyrazoles”, Chem Heterocycl Comp, 58:11 (2022), 588  crossref
    13. Qi Zhang, Chunlin He, Siping Pang, “Synthesis of heterocyclic (triazole, furoxan, furazan) fused pyridazine di-N-oxides via hypervalent iodine oxidation”, New J. Chem., 46:30 (2022), 14324  crossref
    14. Ahmed A. M. Ahmed, Ahmed E. M. Mekky, Sherif M. H. Sanad, “New bis(pyrazolo[3,4-b]pyridines) and bis(thieno[2,3-b]pyridines) as potential acetylcholinesterase inhibitors: synthesis, in vitro and SwissADME prediction study”, J IRAN CHEM SOC, 19:11 (2022), 4457  crossref
    15. Leonid L. Fershtat, Egor S. Zhilin, “Recent Advances in the Synthesis and Biomedical Applications of Heterocyclic NO-Donors”, Molecules, 26:18 (2021), 5705  crossref
    16. Yuriy N. Markitanov, Vadim M. Timoshenko, Sergiy S. Mykhaylychenko, Eduard B. Rusanov, Alexandr I. Khyzhan, Yuriy G. Shermolovich, “[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with diazo compounds and nitrilimines – synthesis of pyrazolines and pyrazoles”, Chem Heterocycl Comp, 57:11 (2021), 1107  crossref
    Citing articles in Google Scholar: Russian citations, English citations
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