{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,31]],"date-time":"2026-10-31T07:39:35Z","timestamp":1793432375644,"version":"4.5.0"},"reference-count":39,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2014,11,1]],"date-time":"2014-11-01T00:00:00Z","timestamp":1414800000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"}],"funder":[{"name":"Shiraz University Research Council","award":["90-GR-SC-23"],"award-info":[{"award-number":["90-GR-SC-23"]}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["European Journal of Medicinal Chemistry"],"published-print":{"date-parts":[[2014,11]]},"DOI":"10.1016\/j.ejmech.2014.09.077","type":"journal-article","created":{"date-parts":[[2014,9,28]],"date-time":"2014-09-28T14:32:29Z","timestamp":1411914749000},"page":"364-371","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":33,"special_numbering":"C","title":["Diastereoselective synthesis of potent antimalarial cis-\u03b2-lactam agents through a [2\u00a0+\u00a02] cycloaddition of chiral imines with a chiral ketene"],"prefix":"10.1016","volume":"87","author":[{"given":"Aliasghar","family":"Jarrahpour","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Edris","family":"Ebrahimi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"V\u00e9ronique","family":"Sinou","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christine","family":"Latour","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jean Michel","family":"Brunel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.ejmech.2014.09.077_bib1","volume":"vols. 1\u20133","year":"1982"},{"key":"10.1016\/j.ejmech.2014.09.077_bib2","doi-asserted-by":"crossref","first-page":"973","DOI":"10.1021\/jm970701f","article-title":"Discovery of 1-(4-Fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235):\u2009 a designed, potent, orally active inhibitor of cholesterol absorption","volume":"41","author":"Rosenblum","year":"1998","journal-title":"J.\u00a0Med. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib3","doi-asserted-by":"crossref","first-page":"5541","DOI":"10.1016\/j.ejmech.2010.09.035","article-title":"2-Azetidinone \u2013 a new profile of various pharmacological activities","volume":"45","author":"Mehta","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib4","doi-asserted-by":"crossref","first-page":"2233","DOI":"10.1016\/j.bmcl.2004.02.012","article-title":"Solid-phase synthesis and SAR of 4-carboxy-2-azetidinone mechanism-based tryptase inhibitors","volume":"14","author":"Sutton","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2014.09.077_bib5","first-page":"80","article-title":"Evaluation of anti\u2013hyperglycemic activity of some novel monocyclic beta-lactams","volume":"7","author":"Goel","year":"2004","journal-title":"J.\u00a0Pharm. Pharm. Sci."},{"key":"10.1016\/j.ejmech.2014.09.077_bib6","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/j.canlet.2008.03.047","article-title":"Anti-tumor activity of N-thiolated \u03b2-lactam antibiotics","volume":"268","author":"Chen","year":"2008","journal-title":"Cancer Lett."},{"key":"10.1016\/j.ejmech.2014.09.077_bib7","doi-asserted-by":"crossref","first-page":"3086","DOI":"10.1016\/j.bmcl.2005.04.020","article-title":"Beta-lactam compounds as apparently uncompetitive inhibitors of HIV-1 protease","volume":"15","author":"Tozser","year":"2005","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"10.1016\/j.ejmech.2014.09.077_bib8","doi-asserted-by":"crossref","first-page":"654","DOI":"10.1248\/bpb.23.654","article-title":"Evaluation of analgesic and anti-inflammatory activity of novel \u03b2-lactam monocyclic compounds","volume":"23","author":"Saturnino","year":"2000","journal-title":"Biol. Pharm. Bull."},{"key":"10.1016\/j.ejmech.2014.09.077_bib9","doi-asserted-by":"crossref","first-page":"4740","DOI":"10.1016\/j.tet.2012.04.011","article-title":"Synthesis of novel \u03b2-lactams bearing an anthraquinone moiety, and evaluation of their antimalarial activities","volume":"68","author":"Jarrahpour","year":"2012","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2014.09.077_bib10","doi-asserted-by":"crossref","first-page":"7832","DOI":"10.1016\/j.bmc.2008.06.035","article-title":"Studies on the antifungal properties of N-thiolated \u03b2-lactams","volume":"16","author":"O'Driscoll","year":"2008","journal-title":"Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib11","doi-asserted-by":"crossref","first-page":"6055","DOI":"10.1016\/j.bmc.2011.08.048","article-title":"Lead identification of \u03b2-lactam and related imine inhibitors of the molecular chaperone heat shock protein 90","volume":"19","author":"O'Boyle","year":"2011","journal-title":"J.\u00a0Bioorg. Med. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib12","first-page":"110","article-title":"Synthesis and biological activity of new series of N-[3-(1H-1,2,3-Benzotriazol-1-yl)propyl]-2-(substituted Phenyl)-3-Chloro-4-Oxo-1-Azetidinecarboxamide","volume":"58","author":"Sharma","year":"2011","journal-title":"Acta Chim. Slov."},{"key":"10.1016\/j.ejmech.2014.09.077_bib13","doi-asserted-by":"crossref","first-page":"3037","DOI":"10.1016\/j.tet.2012.02.017","article-title":"Stereoselective synthesis of sugar-based \u03b2-lactam derivatives: docking studies and its biological evaluation","volume":"68","author":"Nagarajan","year":"2012","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2014.09.077_bib14","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1002\/jccs.201190055","article-title":"Synthesis and biological activity of a series of novel N-substituted \u03b2-lactams derived from natural Gallic acid","volume":"58","author":"Cao","year":"2011","journal-title":"J.\u00a0Chin. Chem. Soc."},{"key":"10.1016\/j.ejmech.2014.09.077_bib15","doi-asserted-by":"crossref","first-page":"215","DOI":"10.2174\/1568012023354910","article-title":"\u03b2-Lactams as inhibitors of serine enzymes","volume":"1","author":"Konaklieva","year":"2002","journal-title":"Curr. Med. Chem. Anti-Infective Agents"},{"key":"10.1016\/j.ejmech.2014.09.077_bib16","doi-asserted-by":"crossref","first-page":"245","DOI":"10.2174\/1385272024605050","article-title":"Gold-catalyzed heterocyclizations in alkynyl-and allenyl-\u03b2-lactams","volume":"6","author":"Alcaide","year":"2002","journal-title":"Curr. Org. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib17","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1002\/jlac.19073560106","article-title":"Zur kenntniss der Ketene. diphenylketen","volume":"356","author":"Staudinger","year":"1907","journal-title":"Liebigs Ann. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib18","doi-asserted-by":"crossref","first-page":"1837","DOI":"10.2174\/0929867043364900","article-title":"Asymmetric synthesis of \u03b2-lactams through the Staudinger reaction and their use as building blocks of natural and nonnatural products","volume":"11","author":"Palomo","year":"2004","journal-title":"Curr. Med. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib19","series-title":"The Organic Chemistry of \u03b2-lactams","first-page":"295","author":"Georg","year":"1993"},{"key":"10.1016\/j.ejmech.2014.09.077_bib20","doi-asserted-by":"crossref","first-page":"846","DOI":"10.1016\/j.ejmech.2009.11.024","article-title":"Asymmetric synthesis of anticancer \u03b2-lactams via Staudinger reaction: utilization of chiral ketene from carbohydrate","volume":"45","author":"Banik","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib21","doi-asserted-by":"crossref","first-page":"10686","DOI":"10.1016\/j.tet.2012.06.009","article-title":"Novel synthesis of 3-pyrrole substituted \u03b2-lactams via microwave-induced bismuth nitrate-catalyzed reaction","volume":"68","author":"Bandyopadhyay","year":"2012","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2014.09.077_bib22","doi-asserted-by":"crossref","first-page":"601","DOI":"10.1016\/j.tetasy.2010.03.002","article-title":"Chiral relay in NHC-mediated asymmetric \u03b2-lactam synthesis II; asymmetry from NHCs derived from acyclic 1,2-diamines","volume":"21","author":"Duguet","year":"2010","journal-title":"Tetrahedron: Asymmetry"},{"key":"10.1016\/j.ejmech.2014.09.077_bib23","doi-asserted-by":"crossref","first-page":"7205","DOI":"10.1016\/S0040-4020(01)00675-5","article-title":"[2+2] Cycloaddition reactions of 1-benzyl-2,4-diphenyl-1,3-diazabuta-1,3-diene with chiral ketenes","volume":"57","author":"Abbiati","year":"2001","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2014.09.077_bib24","doi-asserted-by":"crossref","first-page":"6626","DOI":"10.1021\/ja0258226","article-title":"The development of the first catalyzed reaction of ketenes and imines: catalytic, asymmetric synthesis of \u03b2-lactams","volume":"124","author":"Taggi","year":"2002","journal-title":"J.\u00a0Am. Chem. Soc."},{"key":"10.1016\/j.ejmech.2014.09.077_bib25","doi-asserted-by":"crossref","first-page":"1657","DOI":"10.1016\/j.tetlet.2006.12.091","article-title":"Catalytic, asymmetric synthesis \u03b1-phenoxy-\u03b2-aryl-\u03b2-lactams","volume":"48","author":"Huang","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.ejmech.2014.09.077_bib26","first-page":"547","volume":"vol. 3","author":"Leffler","year":"1955"},{"key":"10.1016\/j.ejmech.2014.09.077_bib27","doi-asserted-by":"crossref","first-page":"6620","DOI":"10.1016\/j.tet.2013.05.121","article-title":"A\u00a0facile and effective synthesis of 2-azetidinones via phosphonitrilic chloride","volume":"69","author":"Zarei","year":"2013","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2014.09.077_bib28","doi-asserted-by":"crossref","first-page":"679","DOI":"10.1002\/jhet.5570420430","article-title":"novel method to synthesize docetaxel and its isomer with high yields","volume":"42(","author":"Qi","year":"2005","journal-title":"J.\u00a0Heterocycl. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib29","doi-asserted-by":"crossref","first-page":"6191","DOI":"10.1021\/jo1010679","article-title":"Heterogeneous chiral copper complexes of amino alcohol for asymmetric nitroaldol reaction","volume":"75","author":"Abdi","year":"2010","journal-title":"J.\u00a0Org. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib30","doi-asserted-by":"crossref","first-page":"2859","DOI":"10.1080\/00397910600770698","article-title":"Facile synthesis of (S,S)1,2 Diacylamides and (S,S) 1,2 Diamines with C 2 Symmetry","volume":"36","author":"Ai","year":"2006","journal-title":"Synth. Commun."},{"key":"10.1016\/j.ejmech.2014.09.077_bib31","doi-asserted-by":"crossref","first-page":"4911","DOI":"10.1016\/S0040-4020(03)00706-3","article-title":"Chiral biomimetic NADH models in the benzo[b]-1,6-naphthyridine series. A novel class of stable, reactive and highly enantioselective NADH mimics","volume":"59","author":"Vasse","year":"2003","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2014.09.077_bib32","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1139\/v87-014","article-title":"\u03b2-Lactams. XII.: a study of the synthesis of N-unsubstituted \u03b2-lactams, and of 4-styryl monobactams","volume":"65","author":"Dugat","year":"1987","journal-title":"Can. J. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib33","doi-asserted-by":"crossref","first-page":"6049","DOI":"10.1016\/S0040-4039(00)61724-0","article-title":"A\u00a0simple, highly regioselective, one-pot stereoselective synthesis of tertiary \u03b1-hydroxyesters: a tandem oxidation\/benzilic ester rearrangement","volume":"34","author":"Bourzat","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"10.1016\/j.ejmech.2014.09.077_bib34","doi-asserted-by":"crossref","first-page":"1237","DOI":"10.1007\/BF00809355","article-title":"Enantioselektive Cyclopropanierung von 1,1-Diphenylethylen und Diazoessigester mit Kupfer-Katalysatoren","volume":"115","author":"Brunner","year":"1984","journal-title":"Monatsh. Chem."},{"key":"10.1016\/j.ejmech.2014.09.077_bib35","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1039\/p19850000849","article-title":"Dynamic stereochemistry of imines and derivatives. Part 18. Photosynthesis and photoracemization of optically active oxaziridines","author":"Boyd","year":"1985","journal-title":"J.\u00a0Chem. Soc. Perkin Trans. I"},{"key":"10.1016\/j.ejmech.2014.09.077_bib36","doi-asserted-by":"crossref","first-page":"10339","DOI":"10.1016\/j.tet.2009.10.063","article-title":"Chiral amine-induced stereoselectivity in trans-\u03b2-lactam formation via Staudinger cycloaddition","volume":"65","author":"Todorov","year":"2009","journal-title":"Tetrahedron"},{"key":"10.1016\/j.ejmech.2014.09.077_bib37","series-title":"Purificatinon of Laboratory Chemicals","author":"Amarego","year":"2003"},{"key":"10.1016\/j.ejmech.2014.09.077_bib38","doi-asserted-by":"crossref","first-page":"673","DOI":"10.1126\/science.781840","article-title":"Human malaria parasites in continuous culture","volume":"193","author":"Trager","year":"1976","journal-title":"Science"},{"key":"10.1016\/j.ejmech.2014.09.077_bib39","doi-asserted-by":"crossref","first-page":"418","DOI":"10.2307\/3280287","article-title":"Synchronization of plasmodium falciparum erythrocytic stages in culture","volume":"95","author":"Lambros","year":"1979","journal-title":"J.\u00a0Parasitol."}],"container-title":["European Journal of Medicinal Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523414008964?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0223523414008964?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2018,9,28]],"date-time":"2018-09-28T22:50:20Z","timestamp":1538175020000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0223523414008964"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,11]]},"references-count":39,"alternative-id":["S0223523414008964"],"URL":"https:\/\/doi.org\/10.1016\/j.ejmech.2014.09.077","relation":{},"ISSN":["0223-5234"],"issn-type":[{"value":"0223-5234","type":"print"}],"subject":[],"published":{"date-parts":[[2014,11]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Diastereoselective synthesis of potent antimalarial cis-\u03b2-lactam agents through a [2\u00a0+\u00a02] cycloaddition of chiral imines with a chiral ketene","name":"articletitle","label":"Article Title"},{"value":"European Journal of Medicinal Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.ejmech.2014.09.077","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"Copyright \u00a9 2014 Elsevier Masson SAS. All rights reserved.","name":"copyright","label":"Copyright"}]}}