{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T11:49:34Z","timestamp":1777463374849,"version":"3.51.4"},"reference-count":51,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2019,7,1]],"date-time":"2019-07-01T00:00:00Z","timestamp":1561939200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2019,7,1]],"date-time":"2019-07-01T00:00:00Z","timestamp":1561939200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"}],"funder":[{"DOI":"10.13039\/501100004695","name":"Inyuvesi Yakwazulu-Natali","doi-asserted-by":"publisher","award":["61388963"],"award-info":[{"award-number":["61388963"]}],"id":[{"id":"10.13039\/501100004695","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Phytochemistry"],"published-print":{"date-parts":[[2019,7]]},"DOI":"10.1016\/j.phytochem.2019.03.014","type":"journal-article","created":{"date-parts":[[2019,4,20]],"date-time":"2019-04-20T16:14:04Z","timestamp":1555776844000},"page":"187-194","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":8,"special_numbering":"C","title":["Synthesis of potent neuroprotective butenolides based on plant smoke derived 3,4,5-Trimethylfuran-2(5H)-one and 3-methyl-2H-furo[2,3-c]pyrone-2-one"],"prefix":"10.1016","volume":"163","author":[{"given":"Devashan","family":"Naidoo","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Martin","family":"Po\u0161ta","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ayan","family":"Roy","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Manoj","family":"Kulkarni","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Johannes","family":"Van Staden","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.phytochem.2019.03.014_bib1","doi-asserted-by":"crossref","first-page":"e55","DOI":"10.1158\/0008-5472.CAN-17-0511","article-title":"DINC 2.0: a new protein-peptide docking webserver using an incremental approach","volume":"77","author":"Antunes","year":"2017","journal-title":"Cancer Res."},{"key":"10.1016\/j.phytochem.2019.03.014_bib2","doi-asserted-by":"crossref","first-page":"1529","DOI":"10.4155\/fmc.10.237","article-title":"Observations on screening-based research and some concerning trends in the literature","volume":"2","author":"Baell","year":"2010","journal-title":"Future Med. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib3","volume":"vol. 1","author":"Burkill","year":"1985"},{"key":"10.1016\/j.phytochem.2019.03.014_bib4","doi-asserted-by":"crossref","first-page":"1173","DOI":"10.1016\/0024-3205(91)90455-K","article-title":"Effects of tobacco smoke constituents on MPTP-induced toxicity and monoamine oxidase activity in the mouse brain","volume":"48","author":"Carr","year":"1991","journal-title":"Life Sci."},{"key":"10.1016\/j.phytochem.2019.03.014_bib5","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1016\/j.ejphar.2017.10.023","article-title":"A novel selective MAO-B inhibitor with neuroprotective and anti-Parkinsons properties","volume":"818","author":"Chan","year":"2018","journal-title":"Eur. J. Pharmacol."},{"key":"10.1016\/j.phytochem.2019.03.014_bib6","doi-asserted-by":"crossref","first-page":"3099","DOI":"10.1021\/ci300367a","article-title":"AadmetSAR: a comprehensive source and free tool for assessment of chemical ADMET properties","volume":"52","author":"Cheng","year":"2012","journal-title":"J. Chem. Inf. Model."},{"key":"10.1016\/j.phytochem.2019.03.014_bib7","doi-asserted-by":"crossref","first-page":"10282","DOI":"10.1021\/jm300871x","article-title":"Structures of human acetylcholinesterase in complex with pharmacologically important ligands","volume":"55","author":"Cheung","year":"2012","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib8","doi-asserted-by":"crossref","first-page":"3127","DOI":"10.1021\/mp300234q","article-title":"In silico prediction of aqueous solubility: a multimodel protocol based on chemical similarity","volume":"9","author":"Chevillard","year":"2012","journal-title":"Mol. Pharmaceuticals"},{"key":"10.1016\/j.phytochem.2019.03.014_bib9","doi-asserted-by":"crossref","first-page":"42717","DOI":"10.1038\/srep42717","article-title":"Swiss ADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules","volume":"7","author":"Daina","year":"2017","journal-title":"Sci. Rep."},{"key":"10.1016\/j.phytochem.2019.03.014_bib10","doi-asserted-by":"crossref","first-page":"12684","DOI":"10.1073\/pnas.0505975102","article-title":"Three-dimensional structure of human monoamine oxidase A (MAO A): relation to the structures of rat MAO A and human MAO A","volume":"102","author":"De Colibus","year":"2005","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"10.1016\/j.phytochem.2019.03.014_bib11","doi-asserted-by":"crossref","first-page":"1115","DOI":"10.1016\/j.chembiol.2014.08.013","article-title":"Oral druggable space beyond the rule of 5: insights from drugs and clinical candidates","volume":"21","author":"Doak","year":"2014","journal-title":"Chem. Biol."},{"key":"10.1016\/j.phytochem.2019.03.014_bib12","doi-asserted-by":"crossref","first-page":"3867","DOI":"10.1021\/jm000292e","article-title":"Prediction of drug absorption using multivariate statistics","volume":"43","author":"Egan","year":"2000","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib13","doi-asserted-by":"crossref","first-page":"457","DOI":"10.1016\/j.jep.2005.08.049","article-title":"Antibacterial, antiinflammatory, anti-acetylcholinesterase and mutagenic effects of extracts obtained from some trees used in South African traditional medicine","volume":"102","author":"Eldeen","year":"2005","journal-title":"J. Ethnopharmacol."},{"key":"10.1016\/j.phytochem.2019.03.014_bib14","doi-asserted-by":"crossref","first-page":"1200","DOI":"10.2174\/1568026615666150915111741","article-title":"Sulfur containing scaffolds in drugs: synthesis and application in medicinal chemistry","volume":"16","author":"Feng","year":"2016","journal-title":"Curr. Top. Med. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib15","doi-asserted-by":"crossref","first-page":"5719","DOI":"10.1016\/j.tetlet.2005.06.077","article-title":"Synthesis of the seed germination stimulant 3-methyl-2H-furo [2,3-c] pyran-2-one","volume":"46","author":"Flematti","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.phytochem.2019.03.014_bib16","doi-asserted-by":"crossref","first-page":"9475","DOI":"10.1021\/jf9028128","article-title":"Identification of alkyl substituted 2H-Furo[2,3-c]pyran-2-ones as germination stimulants present in smoke","volume":"57","author":"Flematti","year":"2009","journal-title":"J. Agric. Food Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib17","doi-asserted-by":"crossref","first-page":"2189","DOI":"10.1021\/jf0633241","article-title":"Preparation of 2H-furo[2,3-c]pyran-2-one derivatives and evaluation of their germination promoting activity","volume":"55","author":"Flematti","year":"2007","journal-title":"J. Agric. Food Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib18","doi-asserted-by":"crossref","first-page":"1195","DOI":"10.1021\/jf1041728","article-title":"Production of the seed germination stimulant karrikinolide from combustion of simple carbohydrates","volume":"59","author":"Flematti","year":"2011","journal-title":"J. Agric. Food Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib19","doi-asserted-by":"crossref","first-page":"733","DOI":"10.1038\/379733a0","article-title":"Inhibition of monoamine oxidase B in the brains of smokers","volume":"22","author":"Fowler","year":"1996","journal-title":"Nature"},{"key":"10.1016\/j.phytochem.2019.03.014_bib20","doi-asserted-by":"crossref","first-page":"817","DOI":"10.1021\/jm701122q","article-title":"Generation of a set of simple, interpretable ADMET rules of thumb","volume":"51","author":"Gleeson","year":"2008","journal-title":"J. Med. Chem."},{"issue":"4","key":"10.1016\/j.phytochem.2019.03.014_bib21","doi-asserted-by":"crossref","first-page":"358","DOI":"10.2174\/156802611794480927","article-title":"In-silico ADME models: a general assessment of their utility in drug discovery and applications","volume":"11","author":"Gleeson","year":"2011","journal-title":"Curr. Top. Med. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib22","article-title":"Ethnopharmacological survey of six medicinal plants from Mali, West-Africa","volume":"26","author":"Gronhaug","year":"2008","journal-title":"J. Ethnobiol. Ethnomed."},{"key":"10.1016\/j.phytochem.2019.03.014_bib23","doi-asserted-by":"crossref","first-page":"2311","DOI":"10.1002\/cber.19921251019","article-title":"Photodecarboxyla-tion of 2(3H)-thiophenones","volume":"125","author":"Hinrichs","year":"1992","journal-title":"Chem. Ber."},{"key":"10.1016\/j.phytochem.2019.03.014_bib24","doi-asserted-by":"crossref","first-page":"384","DOI":"10.1006\/abio.1996.9911","article-title":"A continuous spectrophotometric assay for monoamine oxidase and related enzymes in tissue homogenates","volume":"244","author":"Holt","year":"1997","journal-title":"Anal. Biochem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib25","doi-asserted-by":"crossref","first-page":"1440","DOI":"10.1002\/jps.20075","article-title":"Combined application of parallel artificial membrane permeability assay and Caco-2 permeability assays in drug discovery","volume":"93","author":"Kerns","year":"2004","journal-title":"J. Pharm. Sci."},{"key":"10.1016\/j.phytochem.2019.03.014_bib26","doi-asserted-by":"crossref","first-page":"3656","DOI":"10.1093\/bioinformatics\/btx491","article-title":"FAF-Drugs4: free ADME-tox filtering computations for chemical biology and early stages drug discovery","volume":"33","author":"Lagorce","year":"2017","journal-title":"Bioinformatics"},{"key":"10.1016\/j.phytochem.2019.03.014_bib27","series-title":"ADMET for Medicinal Chemists: A Practical Guide","article-title":"In silico ADME\/tox predictions","author":"Lagorce","year":"2011"},{"key":"10.1016\/j.phytochem.2019.03.014_bib28","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1016\/j.addr.2016.01.018","article-title":"Molecular inflation, attrition and the rule of five","volume":"101","author":"Lesson","year":"2016","journal-title":"Adv. Drug Deliv. Rev."},{"key":"10.1016\/j.phytochem.2019.03.014_bib29","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.mrgentox.2014.12.006","article-title":"Genotoxicity testing of 3,4,5-trimethylfuran-2(5H)-one, a compound from plant derived smoke with germination inhibitory activity","volume":"778","author":"Light","year":"2015","journal-title":"Mutat. Res."},{"key":"10.1016\/j.phytochem.2019.03.014_bib30","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.sajb.2008.10.004","article-title":"Smoke-derived butenolides: towards understanding its biological effects","volume":"75","author":"Light","year":"2009","journal-title":"South Afr. J. Bot."},{"key":"10.1016\/j.phytochem.2019.03.014_bib31","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1016\/S0169-409X(00)00129-0","article-title":"Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings","volume":"46","author":"Lipinski","year":"2001","journal-title":"Adv. Drug Deliv. Rev."},{"key":"10.1016\/j.phytochem.2019.03.014_bib32","first-page":"33","article-title":"Open Babel: an open chemical toolbox","volume":"3","author":"O'Boyle","year":"2011","journal-title":"J. Chem. Inform."},{"key":"10.1016\/j.phytochem.2019.03.014_bib33","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1007\/s002890050170","article-title":"Asymmetric polymerization of N-substituted maleimides with organolithium \u2013 bisoxazolines complex","volume":"39","author":"Onimura","year":"1997","journal-title":"Polym. Bull."},{"key":"10.1016\/j.phytochem.2019.03.014_bib34","first-page":"495","article-title":"An evaluation of the implementation of the Cramer classification scheme in the Toxtree software. SAR. QSAR","volume":"19","author":"Patlewicz","year":"2008","journal-title":"Environ. Res."},{"key":"10.1016\/j.phytochem.2019.03.014_bib35","series-title":"Uses and Abuses of Plant-Derived Smoke: its Ethnobotany as Hallucinogens, Perfume, Incense and Medicine","author":"Pennacchio","year":"2010"},{"key":"10.1016\/j.phytochem.2019.03.014_bib36","doi-asserted-by":"crossref","first-page":"4066","DOI":"10.1021\/acs.jmedchem.5b00104","article-title":"pkCSM: predicting small-molecule pharmacokinetic and toxicity properties using graph-based signatures","volume":"58","author":"Pires","year":"2015","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib37","doi-asserted-by":"crossref","first-page":"1235","DOI":"10.1016\/j.jplph.2013.04.002","article-title":"Structure-activity relationship of analogs of 3,4,5-trimethylfuran-2(5H)-one with germination inhibitory activities","volume":"170","author":"Po\u0161ta","year":"2013","journal-title":"J. Plant Physiol."},{"key":"10.1016\/j.phytochem.2019.03.014_bib38","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1007\/s10725-016-0237-0","article-title":"Structure-activity relationships of N- and S-analogs of the seed germination inhibitor (3,4,5-trimethylfuran-2(5H)-one) for mode of action elucidation","volume":"82","author":"Po\u0161ta","year":"2017","journal-title":"Plant Growth Regul."},{"key":"10.1016\/j.phytochem.2019.03.014_bib39","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1021\/acs.jmedchem.5b00361","article-title":"Pan assay interference compounds (PAINS) and other promiscuous compounds in antifungal research","volume":"59","author":"Pouliot","year":"2016","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib40","doi-asserted-by":"crossref","first-page":"W443","DOI":"10.1093\/nar\/gkv315","article-title":"PLIP: fully automated protein-ligand interaction profiler","volume":"43","author":"Salentin","year":"2015","journal-title":"Nucleic Acids Res."},{"key":"10.1016\/j.phytochem.2019.03.014_bib41","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1021\/ci800305f","article-title":"OSIRIS, an entirely in-house developed drug discovery informatics system","volume":"49","author":"Sander","year":"2009","journal-title":"J. Chem. Inf. Model."},{"key":"10.1016\/j.phytochem.2019.03.014_bib42","doi-asserted-by":"crossref","first-page":"1355","DOI":"10.1107\/S0907444904011679","article-title":"PRODGR: a tool for high-throughput crystallography of protein-ligand complexes","volume":"60","author":"Sch\u00fcttelkopf","year":"2004","journal-title":"Acta Crystallogr. D Biol. Crystallogr."},{"key":"10.1016\/j.phytochem.2019.03.014_bib43","doi-asserted-by":"crossref","first-page":"5750","DOI":"10.1021\/jo1010476","article-title":"Short synthesis of the seed germination inhibitor 3,4,5-trimethyl-2(5H)-furanone","volume":"75","author":"Surmont","year":"2010","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib44","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1002\/jcc.21334","article-title":"AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading","volume":"31","author":"Trott","year":"2010","journal-title":"J. Comput. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib45","doi-asserted-by":"crossref","first-page":"113","DOI":"10.3390\/molecules23010113","article-title":"Design, Synthesis and biological evaluation of novel N-pyridyl-hydrazone derivatives as potential monoamine oxidase (MAO) inhibitors","volume":"23","author":"Turan-Zitouni","year":"2018","journal-title":"Molecules"},{"key":"10.1016\/j.phytochem.2019.03.014_bib46","doi-asserted-by":"crossref","first-page":"1760","DOI":"10.1002\/cbdv.200900056","article-title":"Improving compound quality in vitro and in silico physiochemical profiling","volume":"6","author":"Van de Waterbeemd","year":"2009","journal-title":"Chem. Biodivers."},{"key":"10.1016\/j.phytochem.2019.03.014_bib47","doi-asserted-by":"crossref","first-page":"2615","DOI":"10.1021\/jm020017n","article-title":"Molecular properties that influence the oral bioavailability of drug candidates","volume":"45","author":"Veber","year":"2002","journal-title":"J. Med. Chem."},{"key":"10.1016\/j.phytochem.2019.03.014_bib48","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/j.mrgentox.2006.07.005","article-title":"Genetic toxicity of 3-methyl-2H-furo[2.3-c]pyran-2-one, an important biologically active compound from plant-derived smoke","volume":"611","author":"Verschaeve","year":"2006","journal-title":"Mutat. Res."},{"key":"10.1016\/j.phytochem.2019.03.014_bib49","series-title":"Neurological Disorders: Public Health Challenges","author":"World Health Organization","year":"2006"},{"key":"10.1016\/j.phytochem.2019.03.014_bib50","doi-asserted-by":"crossref","first-page":"725","DOI":"10.1007\/s00702-007-0679-7","article-title":"Docking of novel reversible monoamine oxidase-B inhibitors: efficient prediction of ligand binding sites and estimation of inhibitors thermodynamic properties","volume":"114","author":"Yele\u00e7ki","year":"2007","journal-title":"J. Neural Transm."},{"key":"10.1016\/j.phytochem.2019.03.014_bib51","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1016\/0024-3205(87)90446-2","article-title":"Irreversible inhibition of monoamine oxidase by some components of cigarette smoke","volume":"44","author":"Yu","year":"1987","journal-title":"Life Sci."}],"container-title":["Phytochemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0031942218307982?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0031942218307982?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,9,21]],"date-time":"2025-09-21T18:38:34Z","timestamp":1758479914000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0031942218307982"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,7]]},"references-count":51,"alternative-id":["S0031942218307982"],"URL":"https:\/\/doi.org\/10.1016\/j.phytochem.2019.03.014","relation":{},"ISSN":["0031-9422"],"issn-type":[{"value":"0031-9422","type":"print"}],"subject":[],"published":{"date-parts":[[2019,7]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Synthesis of potent neuroprotective butenolides based on plant smoke derived 3,4,5-Trimethylfuran-2(5H)-one and 3-methyl-2H-furo[2,3-c]pyrone-2-one","name":"articletitle","label":"Article Title"},{"value":"Phytochemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.phytochem.2019.03.014","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2019 Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}]}}