10497-40-2Relevant academic research and scientific papers
Synthesis and cytotoxic activities of semisynthetic zearalenone analogues
Tadpetch, Kwanruthai,Kaewmee, Benyapa,Chantakaew, Kittisak,Kantee, Kawalee,Rukachaisirikul, Vatcharin,Phongpaichit, Souwalak
, p. 3612 - 3616 (2016)
Zearalenone is a β-resorcylic acid macrolide with various biological activities. Herein we report the synthesis and cytotoxic activities of 34 zearalenone analogues against human oral epidermoid carcinoma (KB) and human breast adenocarcinoma (MCF-7) cells as well as noncancerous Vero cells. Some zearalenone analogues showed moderately enhanced cytotoxic activities against the two cancer cell lines. We have discovered the potential lead compounds with diminished or no cytotoxicity to Vero cells. Preliminary structure–activity relationship studies revealed that the double bond at the 1′ and 2′ positions of zearalenone core was crucial for cytotoxic activities on both cell lines. In addition, for zearalenol analogues, the unprotected hydroxyl group at C-2 and an alkoxy substituent at C-4 played key roles on cytotoxic effects of both cell lines.
Catalytic asymmetric total synthesis of (S)-(-)-zearalenone, a novel lipoxygenase inhibitor
Baggelaar, Marc P.,Huang, Yange,Feringa, Ben L.,Dekker, Frank J.,Minnaard, Adriaan J.
, p. 5271 - 5274 (2013/09/02)
A catalytic asymmetric synthesis of (S)-(-)-zearalenone is reported using asymmetric allylic alkylation for the introduction of the stereocenter. (S)-(-)-Zearalenone turned out to be a novel lipoxygenase inhibitor.
A concise total synthesis of (S)-zearalenone and zeranol
Yadav,Murthy, P. Vishnu
, p. 2117 - 2124 (2011/08/05)
A convergent total synthesis of the naturally occurring, 14-membered macrolides (S)-zearalenone and zeranol has been achieved through application of the Diels-Alder reaction, Jacobsen kinetic resolution, Mitsunobu coupling, ring-closing metathesis, and hy
Access to resorcylic acid lactones via phosphonate based intramolecular olefination
Napolitano, Carmela,McArdle, Patrick,Murphy, Paul V.
supporting information; experimental part, p. 7404 - 7407 (2011/02/22)
An approach to resorcylic acid lactones is described, exploiting an intramolecular olefination reaction for the generation of the 14-membered macrolactone. The synthetic route gave zearalenone precursors, and the preparations of other RAL analogues, trans
Total Synthesis of the Mycotoxin (-)-Zearalenone based on Macrocyclisation using a Cinnamyl Radical Intermediate
Hitchcock, Stephen A.,Pattenden, Gerald
, p. 1323 - 1328 (2007/10/02)
A concise synthesis of optically active (-)-zearalenone, which uses a novel 14-endo-trig macrocyclisation from a cinnamyl radical intermediate onto an α,β-enone electrophore as a key feature, is described.
Asymmetric Synthesis of (S)-Zearalenone Dimethyl Ether, an Orsellinic Acid Type Macrolide
Solladie, Guy,Maestro, M. Carmen,Rubio, Almudena,Pedregal, Concepcion,Carreno, M. Carmen,Ruano, Jose L. Garcia
, p. 2317 - 2322 (2007/10/02)
The synthesis of (S)-zearalenone dimethyl ether is described.The chiral part of the molecule was obtained by asymmetric synthesis monitored by a chiral sulfoxide group and introduced in the very last steps of the synthesis.
Thermostable Enzymes in Organic Synthesis, Part 6. Total synthesis of (S)-(-)-Zearalenone using a TBADH-Generated Trifunctional Chiron
Keinan, Ehud,Sinha, Subhash C.,Sinha-Bagchi, Anjana
, p. 3333 - 3340 (2007/10/02)
Chiral alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalysed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis.In particular, the ability of TBADH to discriminate between two ketones having equal chemical reactivity is demonstrated by enzymatic reduction of dec-9-ene-2,6-dione to produce optically pure (S)-2-hydroxydec-9-en-6-one.The total synthesis of (S)-(-)-zearalenone with optical purity that exceeds 99.5percent has been achieved by using the latter compound as a starting material.
Synthesis of macrocycles via allylic radical intermediates. A total synthesis of (-)-zearalenone
Hitchcock, Stephen A.,Pattenden, Gerald
, p. 3641 - 3644 (2007/10/02)
A concise synthesis of optically active (-)-zearalenone (1) which uses a novel 14-endo trig macrocyclisation from an allylic radical intermediate (Scheme 1) as a key feature, is described.
Microbial Transformation of Zearalenone. 2. Reduction, Hydroxylation, and Methylation Products
El-Sharkawy, Saleh H.,Abul-Hajj, Yusuf J.
, p. 515 - 519 (2007/10/02)
Microbial transformations have been employed as a means of preparing analogues of the resorcylic acid lactone zearalenone.Microbial transformation products were initially identified by thin-layer chromatography of fermentation extracts and then prepared by large-scale incubations.Each metabolite was subjected to structural elucidation employing carbon-13 and proton NMR, mass spectrometry, and infrared analysis.Metabolites were identified as α- and β-zearalenol, α- and β-zearalanol, zearalanone, 8'(S)-hydroxyzearalenone, 2,4-dimethoxyzearalenone, and 2-methoxyzearalenone.Binding affinities to rat uterine estrogen receptors were carried out.Only those metabolites having a free 4-phenolic group were capable of binding to the estrogen receptor.However, 8'-hydroxyzearalenone, even with a 4-phenolic hydroxyl, did not bind to the receptor.It is possible that hydrogen bonding of the aliphatic hydroxyl groups to the C-6' carbonyl of zearalenone or equilibrium between the hydroxy ketone and its tautomeric hemiketal may lead to distortion of the conformation of the molecule resulting in loss of binding to the receptor.
