{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,5]],"date-time":"2026-06-05T03:18:57Z","timestamp":1780629537987,"version":"3.54.1"},"reference-count":27,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2022,11,22]],"date-time":"2022-11-22T00:00:00Z","timestamp":1669075200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceuticals"],"abstract":"<jats:p>Here, we investigated the reaction of 1,3-dipolar cycloaddition of 1,3-diazido-2-nitro-2- azapropane (DANP) to propargyl alcohol over a copper-based catalyst and identified the optimum reaction conditions that enable the synthesis of 2-nitro-1,3-bis(4,4\u2032-dihydroxymethyl)-1,2,3-triazolyl-2-azapropane (1) in more than 84% yield. The reaction between DANP, 1,5-diazido-3-nitrazapentane, and phenylacetylene produced the respective 1,2,3-triazole derivatives in 83% and 71% yields, respectively. The structures of the resultant compounds were validated by infrared and NMR spectroscopies and elemental analysis. The structure of 1 was proved by single-crystal X-ray diffraction. This study demonstrated that 1 exhibits a dose-dependent antiarrhythmic activity towards calcium-chloride-induced arrhythmia and refers to Class III: moderately hazardous substances.<\/jats:p>","DOI":"10.3390\/ph15121443","type":"journal-article","created":{"date-parts":[[2022,11,22]],"date-time":"2022-11-22T05:25:45Z","timestamp":1669094745000},"page":"1443","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Investigation of 1,4-Substituted 1,2,3-Triazole Derivatives as Antiarrhythmics: Synthesis, Structure, and Properties"],"prefix":"10.3390","volume":"15","author":[{"given":"Elena O.","family":"Shestakova","sequence":"first","affiliation":[{"name":"Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), 659322 Biysk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7853-6118","authenticated-orcid":false,"given":"Sergey G.","family":"Il\u2019yasov","sequence":"additional","affiliation":[{"name":"Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), 659322 Biysk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Irina A.","family":"Shchurova","sequence":"additional","affiliation":[{"name":"Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), 659322 Biysk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2674-5708","authenticated-orcid":false,"given":"Vera S.","family":"Glukhacheva","sequence":"additional","affiliation":[{"name":"Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), 659322 Biysk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dmitri S.","family":"Il\u2019yasov","sequence":"additional","affiliation":[{"name":"Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), 659322 Biysk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Egor E.","family":"Zhukov","sequence":"additional","affiliation":[{"name":"Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences (IPCET SB RAS), 659322 Biysk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arkady O.","family":"Bryzgalov","sequence":"additional","affiliation":[{"name":"Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences (NIOCh SB RAS), 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tatiana G.","family":"Tolstikova","sequence":"additional","affiliation":[{"name":"Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences (NIOCh SB RAS), 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuri V.","family":"Gatilov","sequence":"additional","affiliation":[{"name":"Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences (NIOCh SB RAS), 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,11,22]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1002\/prep.201200146","article-title":"Synthesis, crystalstructure, andthermalbehaviorsof 3-nitro-1,5-bis(4,4\u2019-dimethylazide)-1,2,3-triazolyl-3-azapentane (NDTAP)","volume":"38","author":"Wang","year":"2013","journal-title":"Propellants Explos. Pyrotech."},{"key":"ref_2","first-page":"2098","article-title":"Synthesis of 1,2,3-triazoles starting from heterocyclic \u03b1-nitrazides","volume":"11","author":"Katorov","year":"2012","journal-title":"Russ. Chem. Bull."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1197","DOI":"10.1007\/s10593-019-02601-7","article-title":"Synthesis of 1-(adamantan-1-yl)-1H-1,2,3-triazolesand their salts by adamantylation in AdOH\u2013HClO4 and AdOH\u2013H2SO4 systems","volume":"55","author":"Sukhanov","year":"2019","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2097","DOI":"10.1016\/j.tetlet.2007.01.130","article-title":"One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal acetylenes and in situ generated azides","volume":"48","author":"Odlo","year":"2007","journal-title":"Tetrahed. Lett."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"444","DOI":"10.1007\/s10593-014-1496-1","article-title":"Prediction of the biological activity spectra of organic compounds using the Pass Online web resource","volume":"50","author":"Filimonov","year":"2014","journal-title":"Chem. Heterocycl. Comp."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3109\/14756360903524304","article-title":"Pharmacological significance of triazole scaffold","volume":"26","author":"Kharb","year":"2011","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"857","DOI":"10.1080\/17460441.2016.1210125","article-title":"Discovery of novel anti-HIV agents via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry-based approach","volume":"11","author":"Gao","year":"2016","journal-title":"Expert Opin. Drug Discov."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2116","DOI":"10.1002\/ajoc.202000494","article-title":"Pentacycloundecane (PCUD) based cage frameworks as potential energetic materials: Syntheses and characterization","volume":"9","author":"Kotha","year":"2020","journal-title":"Asian J. Org. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"10136","DOI":"10.1016\/S0021-9258(18)99200-8","article-title":"The inhibition of receptor-mediated and voltage-dependent calcium entry by the antiproliferative L-651,582","volume":"266","author":"Hupe","year":"1991","journal-title":"J. Biol. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2952","DOI":"10.1021\/cr0783479","article-title":"Cu-catalyzed azide-alkyne cycloaddition","volume":"108","author":"Meldal","year":"2008","journal-title":"Chem. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"9528","DOI":"10.1039\/C5OB01457C","article-title":"Copper-catalysedazide-alkyne cycloadditions (CuAAC): An update","volume":"13","author":"Nicasio","year":"2015","journal-title":"Org. Biomol. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2837","DOI":"10.3390\/molecules20022837","article-title":"Solvent-free copper-catalyzedazide-alkyne cycloaddition under mechanochemical activation","volume":"20","author":"Rinaldi","year":"2015","journal-title":"Molecules"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2154","DOI":"10.1021\/acs.organomet.2c00246","article-title":"Copper-catalyzedazide-alkyne cycloaddition (CuAAC) by functionalized NHC-based polynuclear catalysts: Scope and mechanistic insights","volume":"41","author":"Gallegos","year":"2022","journal-title":"Organometallics"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1021\/ja0471525","article-title":"Copper (I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates","volume":"127","author":"Himo","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1302","DOI":"10.1039\/b904091a","article-title":"Copper-catalyzed azide-alkyne cycloaddition (CuAAC) and beyond: New reactivity of copper (I) acetylides","volume":"39","author":"Hein","year":"2010","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1002\/prep.201100067","article-title":"Preparationof 1,3-diazido-2-nitro-2-azapropanefrom urea","volume":"37","author":"Danilova","year":"2012","journal-title":"Propellants Explos. Pyrotech."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"17548","DOI":"10.1039\/D2NJ03521A","article-title":"Efficient Synthesis of N-(Chloromethyl)nitramines via TiCl4-Catalyzed Chlorodeacetoxylation","volume":"46","author":"Gribov","year":"2022","journal-title":"New J. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Zhang, S., Gao, Z., Lan, D., Jia, Q., Liu, N., Zhang, J., and Kou, K. (2020). Recent advances in synthesis and properties of nitrated-pyrazoles based energetic compounds. Molecules, 25.","DOI":"10.3390\/molecules25153475"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"13547","DOI":"10.1021\/acs.inorgchem.7b02277","article-title":"Energy and biocides storage compounds: Synthesis and characterization of energetic bridged bis(triiodoazoles)","volume":"56","author":"He","year":"2017","journal-title":"Inorg. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"4667","DOI":"10.1002\/ejic.201300382","article-title":"Advanced Open-Chain Nitramines as Energetic Materials: Heterocyclic-Substituted 1,3-Dichloro-2-nitrazapropane","volume":"2013","author":"Penger","year":"2013","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"8929","DOI":"10.1002\/chem.201300747","article-title":"Nitramines with varying sensitivities: Functionalized dipyrazolyl N-nitromethanamines as energetic materials","volume":"19","author":"Zhang","year":"2013","journal-title":"Chem. Eur. J."},{"key":"ref_22","unstructured":"Bottaro, J.C., Schmitt, R.J., Petrie, M.A., and Penwell, P.E. (2001). Energetic Nitramine-Linked Azoles and Hydroxylammonium Salts as Oxidizers, Initiators and Gas Generators. (6,255,512), U.S. Patent."},{"key":"ref_23","unstructured":"Karyakin, Y.V., and Angelov, I.I. (1974). Pure Chemical Substances, Khimiya Publisher. [4th ed.]. Available online: http:\/\/chemteq.ru\/library\/inorganic\/2024.html."},{"key":"ref_24","first-page":"2132","article-title":"A new method of preparing copper oxide from dinitrourea copper salt","volume":"640","author":"Kazantsev","year":"2014","journal-title":"ZAAC"},{"key":"ref_25","first-page":"118","article-title":"Synthesis of ammonium bis(N,N\u2019-dinitrourea)cuprate (II) and copper(II) nanooxide","volume":"1","author":"Rudakov","year":"2016","journal-title":"Polzunovskiy Vestn."},{"key":"ref_26","unstructured":"Simmons, R.L., and Young, M.B. (1984). Azidonitramine. (4,450,110), U.S. Patent."},{"key":"ref_27","unstructured":"Flanagan, J.E., Wilson, E.R., and Frankel, M.B. (1991). 1,5-Diazido-3-Nitrazapentane and Method of Preparation Thereof. (5,013,856A), U.S.Patent."}],"container-title":["Pharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1424-8247\/15\/12\/1443\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:23:18Z","timestamp":1760145798000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1424-8247\/15\/12\/1443"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,11,22]]},"references-count":27,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2022,12]]}},"alternative-id":["ph15121443"],"URL":"https:\/\/doi.org\/10.3390\/ph15121443","relation":{},"ISSN":["1424-8247"],"issn-type":[{"value":"1424-8247","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,11,22]]}}}