7533-25-7Relevant 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
supporting information, p. 3612 - 3616 (2016/07/21)
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 syntheses of (S)-(-)-zearalenone and lasiodiplodin reveal superior metathesis activity of ruthenium carbene complexes with imidazol-2-ylidene ligands
Furstner,Thiel,Kindler,Bartkowska
, p. 7990 - 7995 (2007/10/03)
Total syntheses of the bioactive orsellinic acid derivatives zearalenone 3 and lasiodiplodin 1 are reported based on a ring-closing metathesis (RCM) reaction of styrene precursors as the key steps. These and closely related macrocyclizations are catalyzed
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.
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.
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.
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.
