{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,8]],"date-time":"2026-09-08T23:34:56Z","timestamp":1788910496511,"version":"build-2803163510"},"reference-count":48,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2021,9,29]],"date-time":"2021-09-29T00:00:00Z","timestamp":1632873600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Research Foundation (ZA)","award":["NRF GUN: 118554"],"award-info":[{"award-number":["NRF GUN: 118554"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Sulfonamidochalcones continue to assert themselves as versatile synthetic intermedi-ates and several articles continue to appear in literature describing their synthesis, chemical transformation and biological properties. These compounds are not only of interest from the medicinal chemistry context, their conformations and crystalline structures also continue to attract attention to explore non-covalent (intramolecular and intermolecular) interactions, control molecular conformations, and improve their physicochemical and optical properties. Despite an exhaustive list of examples of the ring-A sulfonamide-appended chalcones described in the literature, there is no com-prehensive review dedicated to their synthesis, structural and biological properties. This review focuses attention on the synthesis, structure and biological properties of the ring-A sulfonamide-appended chalcones (o\/m\/p-sulfonamidochalcones) as well as their potential as non-linear optical materials.<\/jats:p>","DOI":"10.3390\/molecules26195923","type":"journal-article","created":{"date-parts":[[2021,9,30]],"date-time":"2021-09-30T00:03:42Z","timestamp":1632960222000},"page":"5923","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Synthesis, Structural and Biological Properties of the Ring-A Sulfonamido Substituted Chalcones: A Review"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6018-5671","authenticated-orcid":false,"given":"Malose J.","family":"Mphahlele","sequence":"first","affiliation":[{"name":"Department of Chemistry, College of Science, Engineering and Technology, University of South Africa, Private Bag X06, Florida 1710, South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,9,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1007\/s11101-014-9387-8","article-title":"Naturally occurring chalcones and their biological activities","volume":"15","author":"Rozmer","year":"2016","journal-title":"Phytochem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"758","DOI":"10.1016\/j.ejmech.2014.08.033","article-title":"Recent developments in biological activities of chalcones: A mini review","volume":"85","author":"Singh","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1007\/s10311-019-00959-w","article-title":"Chalcone synthesis, properties and medicinal applications: A review","volume":"18","author":"Rammohan","year":"2020","journal-title":"Environ. Chem. Lett."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7762","DOI":"10.1021\/acs.chemrev.7b00020","article-title":"Chalcone: A Privileged Structure in Medicinal Chemistry","volume":"117","author":"Zhuang","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_5","first-page":"5289","article-title":"Sulfonamides: Synthesis and the recent applications in Medicinal Chemistry","volume":"63","author":"Ammar","year":"2020","journal-title":"Egypt. J. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Irfan, R., Mousavi, S., Alazmi, M., and Saleem, R.S.Z. (2020). A Comprehensive Review of Aminochalcones. Molecules, 25.","DOI":"10.3390\/molecules25225381"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"126896","DOI":"10.1016\/j.molstruc.2019.126896","article-title":"Sulphonamide chalcones: Conformationally diverse yet optically similar","volume":"1198","author":"Custodio","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"127845","DOI":"10.1016\/j.molstruc.2020.127845","article-title":"Benzenesulfonyl incorporated chalcones: Synthesis, structural and optical properties","volume":"1208","author":"Custodio","year":"2020","journal-title":"J. Mol. Struct."},{"key":"ref_9","first-page":"884","article-title":"Conformational Variability in Sulfonamide Chalcone Hybrids: Crystal Structure and Cytotoxicity","volume":"27","author":"Perez","year":"2016","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_10","first-page":"3294","article-title":"On the in silico and in vitro anticancer activity of sulfonamide chalcones: Potential JNKK3 inhibitors","volume":"424","author":"Custodio","year":"2018","journal-title":"New J. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1345","DOI":"10.1016\/j.arabjc.2017.11.005","article-title":"Tandem chalcone-sulfonamide hybridization, cyclization and further Claisen\u2013Schmidt condensation: Tuning molecular diversity through reaction time and order and catalyst","volume":"13","author":"Naves","year":"2020","journal-title":"Arab. J. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4383","DOI":"10.1007\/s00044-014-1007-z","article-title":"Synthesis, anti-inflammatory and antioxidant activity of ring-A-monosubstituted chalcone derivatives","volume":"23","author":"Iqbal","year":"2014","journal-title":"Med. Chem. Res."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1448","DOI":"10.1007\/s00044-019-02384-8","article-title":"Different reactivity to glutathione but similar tumor cell toxicity of chalcones and their quinolinone analogues","volume":"28","author":"Custodio","year":"2019","journal-title":"Med. Chem. Res."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"4002","DOI":"10.1021\/cg400666v","article-title":"Sulfonamide Molecular Crystals: Structure, Sublimation Thermodynamic Characteristics, Molecular Packing, Hydrogen Bonds Networks","volume":"13","author":"Perlovich","year":"2013","journal-title":"Cryst. Growth Des."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"127393","DOI":"10.1016\/j.molstruc.2019.127393","article-title":"Structural, spectroscopic and nonlinear optical properties of sulfonamide derivatives; experimental and theoretical study","volume":"1202","author":"Arshad","year":"2020","journal-title":"J. Mol. Struct."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2058","DOI":"10.1002\/jps.1157","article-title":"Hydrogen bonding in sulfonamides","volume":"90","author":"Adsmond","year":"2001","journal-title":"J. Pharm. Sci."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2936","DOI":"10.1021\/acs.cgd.9b00159","article-title":"Characteristic hydrogen bonding observed in the crystals of aromatic sulfonamides: 1D chain assembly of molecules and chiral discrimination on crystallization","volume":"19","author":"Kikkawa","year":"2019","journal-title":"Cryst. Growth Des."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"14073","DOI":"10.1021\/ja063076p","article-title":"Conformational flexibility, internal hydrogen bonding, and passive membrane permeability:\u2009 Successful in silico prediction of the relative permeabilities of cyclic peptides","volume":"128","author":"Rezai","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_19","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."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2475","DOI":"10.1002\/cbic.200900108","article-title":"Development of new and selective Trypanosoma cruzi trans-sialidase inhibitors from sulfonamide chalcones and their derivatives","volume":"10","author":"Kim","year":"2009","journal-title":"ChemBioChem"},{"key":"ref_21","first-page":"99","article-title":"Synthesis of some sulfonamide chalcones of biological interest","volume":"4","author":"Bahekar","year":"2015","journal-title":"IJCPS Int. J. Chem. Phys. Sci."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3426","DOI":"10.1039\/C7NJ03523C","article-title":"Structural insights into a novel anticancer sulfonamide chalcone","volume":"42","author":"Custodio","year":"2018","journal-title":"New J. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"389","DOI":"10.1016\/j.molstruc.2018.07.059","article-title":"Solvent-driven structural adaptation in a novel anticancer sulfonamide chalcone","volume":"1175","author":"Custodio","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"262","DOI":"10.1016\/j.ejmech.2016.08.042","article-title":"Sulfonamide chalcones: Synthesis and in vitro exploration for therapeutic potential against Brugia malayi","volume":"124","author":"Bahekar","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"227","DOI":"10.3998\/ark.5550190.p009.488","article-title":"Cascade Michael-Aldol reaction: Efficient annulation of sulfonamide chalcones into novel cyclohexenones under solvent-free conditions","volume":"2016","author":"Agrawal","year":"2016","journal-title":"Arkivoc"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"131090","DOI":"10.1016\/j.molstruc.2021.131090","article-title":"Characterization, Hirshfeld Surface analysis, DFT study and an in vitro \u03b1-glucosidase\/\u03b1-amylase\/radical scavenging profiling of novel 5-styryl-2-(4-tolylsulfonamido)chalcones","volume":"1245","author":"Mphahlele","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2433","DOI":"10.1080\/00397919208021640","article-title":"N-Heterocycles by cyclization of 2\u2032-NHR-chalcones, 2\u2032-NHR-chalcone dibromides and 2\u2032-NHR-\u03b1-azidochalcones","volume":"22","author":"Tokes","year":"1992","journal-title":"Synth. Commun."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"885","DOI":"10.1016\/S0040-4020(01)81369-7","article-title":"Chalcone derivatives as precursors of 1,2,3,4-tetrahydro-4-quinolones","volume":"46","author":"Donnelly","year":"1990","journal-title":"Tetrahedron"},{"key":"ref_29","first-page":"157","article-title":"Synthesis and spectroscopic studies of 2-aryl-l,2,3,4-tetrahydro-l-methanesulfonyl-4-quinoIones","volume":"52","author":"Mphahlele","year":"1999","journal-title":"South Afr. J. Chem."},{"key":"ref_30","first-page":"60","article-title":"Regio- and stereoselective \u03b1-halogenation of 2-aryl-1-methylsulfonyl-2,3- dihydroquinolin-4(1H)-ones","volume":"54","author":"Mphahlele","year":"2001","journal-title":"S. Afr. J. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"128559","DOI":"10.1016\/j.molstruc.2020.128559","article-title":"Structural comparison of five new halogenated dihydroquinoline-4(1H)-ones","volume":"1219","author":"Vaz","year":"2020","journal-title":"J. Mol. Struct."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"129326","DOI":"10.1016\/j.molstruc.2020.129326","article-title":"In silico-driven identification and structural analysis of nitrodihydroquinolinone pesticide candidates with antifungal activity","volume":"1226","author":"Vaz","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2010","DOI":"10.1016\/j.ejmech.2010.01.049","article-title":"Evaluation of anti-pigmentary effect of synthetic sulfonylamino chalcone","volume":"45","author":"Seo","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Mphahlele, M.J., Gildenhuys, S., and Zamisa, S.J. (2021). Synthesis, Structure and Evaluation of the N-(2-Acetyl-4-(styryl)phenyl)-4-benzenesulfonamide Derivatives for Anticholinesterase and Antioxidant Activities. Crystals, 11.","DOI":"10.3390\/cryst11040341"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1747","DOI":"10.1007\/s00706-016-1812-9","article-title":"Synthesis, structure, and antioxidant activity of methoxy- and hydrox-yl-substituted 2\u2032-aminochalcones","volume":"147","author":"Sulpizio","year":"2016","journal-title":"Mon. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1016\/j.saa.2012.04.003","article-title":"Experimental and theoretical vibrational investigation on the saccharinate ion in aqueous solution","volume":"95","author":"Brizuela","year":"2012","journal-title":"Spectrochim. Acta Part. A Mol. Biomol. Spectrosc."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5514","DOI":"10.1016\/j.bmcl.2005.08.087","article-title":"Sulfonamide chalcone as a new class of \u03b1-glucosidase inhibitors","volume":"15","author":"Seo","year":"2005","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"140","DOI":"10.3390\/molecules18010140","article-title":"Inhibitory Evaluation of Sulfonamide Chalcones on \u03b2-Secretase and Acylcholinesterase","volume":"18","author":"Kang","year":"2013","journal-title":"Molecules"},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Mphahlele, M.J., Agbo, E.N., and Choong, Y.S. (2021). Synthesis, Carbohydrate Enzyme Inhibition, Antioxidant Activity, in Silico Drug-Receptor Interactions and Drug-Like Profiling of the 5-Styryl-2-Aminochalcone Hybrids. Molecules, 26.","DOI":"10.3390\/molecules26092692"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"839","DOI":"10.1016\/j.ejmech.2015.01.051","article-title":"Chalcones and their therapeutic targets for the management of diabetes: Structural and pharmacological perspectives","volume":"92","author":"Mahapatra","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"682","DOI":"10.1016\/j.ejmech.2015.01.036","article-title":"Synthesis, anticancer and radiosensitizing evaluation of some novel sulfonamide derivatives","volume":"92","author":"Ghorab","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_42","first-page":"565","article-title":"Synthesis and Anticancer Activity Assay of Novel Chalcone-Sulfonamide Derivatives","volume":"16","author":"Bonakdar","year":"2017","journal-title":"Iran. J. Pharm. Res."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Silva, C.R.E., Borges, F.F.V., Bernardes, A., Perez, C.N., Silva, D.D.M., and Chen-Chen, L. (2015). Genotoxic, Cytotoxic, Antigenotoxic, and Anticytotoxic Effects of Sulfonamide Chalcone Using the Ames Test and the Mouse Bone Marrow Micronucleus Test. PLoS ONE, 10.","DOI":"10.1371\/journal.pone.0137063"},{"key":"ref_44","first-page":"2308","article-title":"Synthesis, Characterization and Evaluation of in vitro Antitumor Activities of Novel Chalcone-Quinolinone Hybrid Compounds","volume":"29","author":"Moura","year":"2018","journal-title":"J. Braz. Chem. Soc."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1080\/15421406.2014.950003","article-title":"Synthesis, Characterization, Antioxidant, and Antibacterial Activities of 2-Aminochalcones and Crystal Structure of (2E)-1-(2-aminophenyl)-3-(4-ethoxyphenyl)-2-propen-1-one","volume":"609","author":"Ruanwas","year":"2015","journal-title":"Mol. Cryst. Liq. Cryst."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"6355","DOI":"10.1016\/j.bmcl.2013.09.073","article-title":"The functional group on (E)-4,4\u2019\u2013disubstituted stilbenes influences toxicity and antioxidant activity in differentiated PC-12 cells","volume":"23","author":"Garcia","year":"2013","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"417","DOI":"10.1007\/s00706-020-02568-8","article-title":"A facile synthesis, drug-likeness, and in silico molecular docking of certain new azidosulfonamide\u2013chalcones and their in vitro antimicrobial activity","volume":"151","author":"Mustafa","year":"2020","journal-title":"Mon. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1016\/j.optmat.2018.10.007","article-title":"Crystal structure, Hirshfeld and third-order nonlinear optical properties of 3-(4-dimethylamino)phenyl)-1-(4-methoxyphenyl)prop-2-en-1-one: A potential material for optical limiting applications","volume":"86","author":"Shetty","year":"2018","journal-title":"Opt. Mater."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/19\/5923\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:07:32Z","timestamp":1760166452000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/19\/5923"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,9,29]]},"references-count":48,"journal-issue":{"issue":"19","published-online":{"date-parts":[[2021,10]]}},"alternative-id":["molecules26195923"],"URL":"https:\/\/doi.org\/10.3390\/molecules26195923","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,9,29]]}}}