{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,24]],"date-time":"2025-10-24T12:35:40Z","timestamp":1761309340229,"version":"build-2065373602"},"reference-count":41,"publisher":"MDPI AG","issue":"13","license":[{"start":{"date-parts":[[2024,7,3]],"date-time":"2024-07-03T00:00:00Z","timestamp":1719964800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004837","name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades (MICIU), Agencia Estatal de Investigaci\u00f3n (AEI)","doi-asserted-by":"publisher","award":["PID2020-116846GB-C21"],"award-info":[{"award-number":["PID2020-116846GB-C21"]}],"id":[{"id":"10.13039\/501100004837","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The present article describes the synthesis of an isonicotinate-derived meso-arylporphyrin, that has been fully characterized by spectroscopic methods (including fluorescence spectroscopy), as well as elemental analysis and HR-MS. The structure of an n-hexane monosolvate has been determined by single-crystal X-ray diffraction analysis. The radical scavenging activity of this new porphyrin against the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical has been measured. Its antifungal activity against three yeast strains (C. albicans ATCC 90028, C. glabrata ATCC 64677, and C. tropicalis ATCC 64677) has been tested using the disk diffusion and microdilution methods. Whereas the measured antioxidant activity was low, the porphyrin showed moderate but encouraging antifungal activity. Finally, a study of its effect on the germination of lentil seeds revealed interesting allelopathic properties.<\/jats:p>","DOI":"10.3390\/molecules29133163","type":"journal-article","created":{"date-parts":[[2024,7,3]],"date-time":"2024-07-03T06:04:18Z","timestamp":1719986658000},"page":"3163","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis, Characterization, X-ray Molecular Structure, Antioxidant, Antifungal, and Allelopathic Activity of a New Isonicotinate-Derived meso-Tetraarylporphyrin"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7586-1508","authenticated-orcid":false,"given":"Nour Elhouda","family":"Dardouri","sequence":"first","affiliation":[{"name":"Laboratory of Physical Chemistry of Materials (LR01ES19), Faculty of Science of Monastir, University of Monastir, Avenue de l\u2019Environment, Monastir 5019, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Soukaina","family":"Hrichi","sequence":"additional","affiliation":[{"name":"Laboratory of Physical Chemistry of Materials (LR01ES19), Faculty of Science of Monastir, University of Monastir, Avenue de l\u2019Environment, Monastir 5019, Tunisia"},{"name":"Laboratory of Medical and Molecular Parasitology-Mycology (LP3M), Faculty of Pharmacy, University of Monastir, LR12ES08, Monastir 5000, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Pol","family":"Torres","sequence":"additional","affiliation":[{"name":"Section of Organic Chemistry, Department of Inorganic and Organic Chemistry, Faculty of Chemistry, University of Barcelona, C. de Mart\u00ed i Franqu\u00e8s 1-11, 08028 Barcelona, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3145-0165","authenticated-orcid":false,"given":"Raja","family":"Cha\u00e2bane-Banaoues","sequence":"additional","affiliation":[{"name":"Laboratory of Medical and Molecular Parasitology-Mycology (LP3M), Faculty of Pharmacy, University of Monastir, LR12ES08, Monastir 5000, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alessandro","family":"Sorrenti","sequence":"additional","affiliation":[{"name":"Section of Organic Chemistry, Department of Inorganic and Organic Chemistry, Faculty of Chemistry, University of Barcelona, C. de Mart\u00ed i Franqu\u00e8s 1-11, 08028 Barcelona, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6088-4472","authenticated-orcid":false,"given":"Thierry","family":"Roisnel","sequence":"additional","affiliation":[{"name":"Institute of Chemical Sciences of Rennes, UMR 6226, University of Rennes 1, Beaulieu Campus, 35042 Rennes, France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8534-1944","authenticated-orcid":false,"given":"Ilona","family":"Turowska-Tyrk","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Wroc\u0142aw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hamouda","family":"Babba","sequence":"additional","affiliation":[{"name":"Laboratory of Medical and Molecular Parasitology-Mycology (LP3M), Faculty of Pharmacy, University of Monastir, LR12ES08, Monastir 5000, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3511-4676","authenticated-orcid":false,"given":"Joaquim","family":"Crusats","sequence":"additional","affiliation":[{"name":"Section of Organic Chemistry, Department of Inorganic and Organic Chemistry, Faculty of Chemistry, University of Barcelona, C. de Mart\u00ed i Franqu\u00e8s 1-11, 08028 Barcelona, Spain"},{"name":"Institute of Cosmos Science, University of Barcelona, C. de Mart\u00ed i Franqu\u00e8s 1-11, 08028 Barcelona, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6331-1397","authenticated-orcid":false,"given":"Albert","family":"Moyano","sequence":"additional","affiliation":[{"name":"Section of Organic Chemistry, Department of Inorganic and Organic Chemistry, Faculty of Chemistry, University of Barcelona, C. de Mart\u00ed i Franqu\u00e8s 1-11, 08028 Barcelona, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Habib","family":"Nasri","sequence":"additional","affiliation":[{"name":"Laboratory of Physical Chemistry of Materials (LR01ES19), Faculty of Science of Monastir, University of Monastir, Avenue de l\u2019Environment, Monastir 5019, Tunisia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,7,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1553","DOI":"10.1007\/s00432-015-1918-1","article-title":"In vitro and in vivo antitumor activity of a novel porphyrin-based photosensitizer for photodynamic therapy","volume":"141","author":"Chen","year":"2015","journal-title":"J. Cancer Res. Clin. Oncol."},{"key":"ref_2","first-page":"504","article-title":"Synthesis of some new porphyrins and their metalloderivatives as potential sensitizers in photo-dynamic therapy","volume":"10","author":"Rostami","year":"2015","journal-title":"Res. Pharm. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3827","DOI":"10.1002\/1099-0690(200211)2002:22<3827::AID-EJOC3827>3.0.CO;2-Z","article-title":"Photoinitiated Olefin Epoxidation with Molecular Oxygen, Sensitized by Free Base Porphyrins and Promoted by Hexacarbonylmolybdenum in Homogeneous Solution","volume":"2002","author":"Campestrini","year":"2002","journal-title":"Eur. J. Org. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"917","DOI":"10.3762\/bjoc.16.83","article-title":"Recent applications of porphyrins as photocatalysts in organic synthesis: Batch and continuous flow approaches","volume":"16","author":"Bartolomeu","year":"2020","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1793","DOI":"10.1002\/cbic.202000067","article-title":"Porphyrins as Colorimetric and Photometric Biosensors in Modern Bioanalytical Systems","volume":"21","author":"Kielmann","year":"2020","journal-title":"ChemBioChem"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2485","DOI":"10.1002\/elan.201800421","article-title":"Nitric Oxide Detection Using Electrochemical Third-generation Biosensors\u2014Based on Heme Proteins and Porphyrins","volume":"30","author":"Gomes","year":"2018","journal-title":"Electroanalysis"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"157720","DOI":"10.1016\/j.apsusc.2023.157720","article-title":"A free base porphyrin as an effective modifier of the cathode interlayer for organic solar cells","volume":"635","author":"Tang","year":"2023","journal-title":"Appl. Surf. Sci."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"86","DOI":"10.1002\/cssc.201701441","article-title":"Near-Infrared-Absorbing Metal-Free Organic, Porphyrin, and Phthalocyanine Sensitizers for Panchromatic Dye-Sensitized Solar Cells","volume":"11","author":"Brogdon","year":"2018","journal-title":"ChemSusChem"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1039\/C7CC08099A","article-title":"Conformational control of nonplanar free base porphyrins: Towards bifunctional catalysts of tunable basicity","volume":"54","author":"Roucan","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Arlegui, A., El-Hachemi, Z., Crusats, J., and Moyano, A. (2018). 5-Phenyl-10,15,20-Tris(4-sulfonatophenyl)porphyrin: Synthesis, Catalysis, and Structural Studies. Molecules, 23.","DOI":"10.3390\/molecules23123363"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"12219","DOI":"10.1039\/C9CC05946F","article-title":"Spontaneous mirror-symmetry breaking coupled to top-bottom chirality transfer: From porphyrin self-assembly to scalemic Diels\u2013Alder adducts","volume":"55","author":"Arlegui","year":"2019","journal-title":"Chem. Commun."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4399","DOI":"10.1002\/ejoc.202000648","article-title":"A pH-Switchable Aqueous Organocatalysis with Amphiphilic Secondary Amine\u2013Porphyrin Hybrids","volume":"2020","author":"Arlegui","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Arlegui, A., Torres, P., Cuesta, V., Crusats, J., and Moyano, A. (2020). Chiral Amphiphilic Secondary Amine-Porphyrin Hybrids for Aqueous Organocatalysis. Molecules, 25.","DOI":"10.3390\/molecules25153420"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"15451","DOI":"10.1021\/jacs.6b09036","article-title":"Porphyrins as Photoredox Catalysts: Experimental and Theoretical Studies","volume":"138","author":"Shan","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Torres, P., Guill\u00e9n, M., Escrib\u00e0, M., Crusats, J., and Moyano, A. (2023). Synthesis of New Amino-Functionalized Porphyrins: Preliminary Study of Their Organophotocatalytic Activity. Molecules, 28.","DOI":"10.3390\/molecules28041997"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"476","DOI":"10.1021\/jo01288a053","article-title":"A simplified synthesis for meso-tetraphenylporphine","volume":"32","author":"Adler","year":"1967","journal-title":"J. Org. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3069","DOI":"10.1016\/S0040-4039(00)96287-7","article-title":"An improved synthesis of tetramesitylporphyrin","volume":"28","author":"Wagner","year":"1987","journal-title":"Tetrahedron Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"8941","DOI":"10.1016\/S0040-4020(01)85364-3","article-title":"Porphyrin Building Blocks for Modular Construction of Bioorganic Model Systems","volume":"50","author":"Lindsey","year":"1994","journal-title":"Tetrahedron"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"120466","DOI":"10.1016\/j.ica.2021.120466","article-title":"Syntheses, crystal structures, photo-physical properties, antioxidant and antifungal activities of Mg(II) 4,4\u2032-bipyridine and Mg(II) pyrazine complexes of the 5,10,15,20 tetrakis(4\u2013bromophenyl)porphyrin","volume":"525","author":"Amiri","year":"2021","journal-title":"Inorg. Chim. Acta"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3999","DOI":"10.1080\/00958972.2010.524930","article-title":"Radical scavenging and in vitro antifungal activities of Cu(II) and Co(II) complexes of the t-butylphenyl derivative of porphyrazine","volume":"63","author":"Keskin","year":"2010","journal-title":"J. Coord. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"121278","DOI":"10.1016\/j.ica.2022.121278","article-title":"DMAP and HMTA manganese(III) meso-tetraphenylporphyrin-based coordination complexes: Syntheses, physicochemical properties, structural and biological activities","volume":"545","author":"Mkacher","year":"2023","journal-title":"Inorg. Chim. Acta"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"132882","DOI":"10.1016\/j.molstruc.2022.132882","article-title":"Study on the synthesis, physicochemical, electrochemical properties, molecular structure and antifungal activities of the 4-pyrrolidinopyridine Mg(II) meso-tetratolylporphyrin complex","volume":"1261","author":"Jabli","year":"2022","journal-title":"J. Mol. Struct."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"109008","DOI":"10.1016\/j.dyepig.2020.109008","article-title":"Utility of dipyrromethane in the synthesis of some new A2B2 porphyrins and their related porphyrin-like derivatives with their evaluation as antimicrobial and antioxidant agents","volume":"191","author":"Fadda","year":"2021","journal-title":"Dye. Pigment."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1483","DOI":"10.1134\/S1070428019100063","article-title":"Functional Derivatives of 4-Formyl-2-methoxyphenyl Pyridine-4-carboxylate","volume":"55","author":"Potkin","year":"2019","journal-title":"Russ. J. Org. Chem."},{"key":"ref_25","unstructured":"(2023, November 22). CCDC 2309201 Contains the Supplementary Crystallographic Data for This Paper. These Data Can Be Obtained Free of Charge. Available online: https:\/\/www.ccdc.cam.ac.uk\/."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"5348","DOI":"10.1002\/ejic.201402546","article-title":"Exploring the Effects of Axial Pseudohalide Ligands on the Photophysical and Cyclic Voltammetry Properties and Molecular Structures of Mg II Tetraphenyl\/porphyrin Complexes","volume":"31","author":"Ezzayani","year":"2014","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"6900","DOI":"10.1039\/C9RA08504A","article-title":"Effect of the coordination of \u03c0-acceptor 4-cyanopyridine ligand on the structural and electronic properties of meso -tetra(para -methoxy) and meso -tetra(para -chlorophenyl) porphyrin cobalt(ii) coordination compounds. Application in the catalytic degradation of methylene blue dye","volume":"10","author":"Guergueb","year":"2020","journal-title":"RSC Adv."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"135559","DOI":"10.1016\/j.molstruc.2023.135559","article-title":"Synthesis and characterization of a new cyanato-N cadmium(II) Meso-arylporphyrin complex by X-ray diffraction analysis, IR, UV\/vis, 1H MNR spectroscopies and TDDFT calculations, optical and electrical properties","volume":"1287","author":"Dardouri","year":"2023","journal-title":"J. Mol. Struct."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5004","DOI":"10.1002\/ejic.201600575","article-title":"Synthesis, Electronic Spectroscopy, Cyclic Voltammetry, Photophysics, Electrical Properties and X-ray Molecular Structures of meso -{Tetrakis [4-(benzoyloxy)phenyl]porphyrinato}zinc(II) Complexes with Aza Ligands","volume":"2016","author":"Nasri","year":"2016","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1016\/j.tsf.2003.10.085","article-title":"Low-band gap polymers for photovoltaic applications","volume":"451\u2013452","author":"Colladet","year":"2004","journal-title":"Thin Solid Films"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1016\/j.ijbiomac.2014.01.033","article-title":"Optimized extraction of polysaccharides from Cymbopogon citratus and its biological activities","volume":"65","author":"Thangam","year":"2014","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"198","DOI":"10.1016\/j.foodchem.2014.05.106","article-title":"Simplification of the DPPH assay for estimating the antioxidant activity of wine and wine by-products","volume":"165","author":"Igartuburu","year":"2014","journal-title":"Food Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/j.biochi.2015.02.001","article-title":"Effect of electron donating groups on polyphenol-based antioxidant dendrimers","volume":"111","author":"Lee","year":"2015","journal-title":"Biochimie"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Hrichi, S., Chaabane-Banaoues, R., Bayar, S., Flamini, G., Oulad El Majdoub, Y., Mangraviti, D., Mondello, L., El Mzoughi, R., Babba, H., and Mighri, Z. (2020). Botanical and Genetic Identification Followed by Investigation of Chemical Composition and Biological Activities on the Scabiosa atropurpurea L. Stem from Tunisian Flora. Molecules, 25.","DOI":"10.3390\/molecules25215032"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"5651","DOI":"10.1016\/j.arabjc.2020.04.006","article-title":"Effect of seasonal variation on the chemical composition and antioxidant and antifungal activities of Convolvulus althaeoides L. leaf extracts","volume":"13","author":"Hrichi","year":"2020","journal-title":"Arab. J. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A Short History of SHELX","volume":"64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. A"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"306","DOI":"10.1107\/S1600576715001132","article-title":"Crystal structure determination and refinement via SIR2014","volume":"48","author":"Burla","year":"2015","journal-title":"J. Appl. Crystallogr."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT\u2014Integrated space-group and crystal-structure determination","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. Fundam. Adv."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1107\/S0021889894010642","article-title":"SORTX\u2014A program for on-screen stick-model editing and autosorting of SHELX files for use on a PC","volume":"28","author":"McArdle","year":"1995","journal-title":"J. Appl. Crystallogr."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1107\/S0021889897003117","article-title":"ORTEP -3 for Windows\u2014A version of ORTEP -III with a Graphical User Interface (GUI)","volume":"30","author":"Farrugia","year":"1997","journal-title":"J. Appl. Crystallogr."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1107\/S0021889807067908","article-title":"Mercury CSD 2.0\u2014New features for the visualization and investigation of crystal structures","volume":"41","author":"Macrae","year":"2008","journal-title":"J. Appl. Crystallogr."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/13\/3163\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T15:09:32Z","timestamp":1760108972000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/13\/3163"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7,3]]},"references-count":41,"journal-issue":{"issue":"13","published-online":{"date-parts":[[2024,7]]}},"alternative-id":["molecules29133163"],"URL":"https:\/\/doi.org\/10.3390\/molecules29133163","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2024,7,3]]}}}