55091-68-4Relevant academic research and scientific papers
Microwave assisted Suzuki reactions for the preparation of the antifungal 3-aryl-5-methyl-2,5-dihydrofuran-2-ones
Mathews, Christopher J.,Taylor, John,Tyte, Melloney J.,Worthington, Paul A.
, p. 538 - 540 (2005)
The Suzuki cross-coupling reaction of arylboronic acids with a bromo-furanone has been developed to prepare a series of substituted 2,5-dihydrofuran-2-ones related to the fungal metabolite, incrustoporin. A protocol of microwave heating was introduced to improve synthesis throughput. Georg Thieme Verlag Stuttgart.
Butenolide synthesis from functionalized cyclopropenones
Nguyen, Sean S.,Ferreira, Andrew J.,Long, Zane G.,Heiss, Tyler K.,Dorn, Robert S.,Row, R. David,Prescher, Jennifer A.
supporting information, p. 8695 - 8699 (2019/10/28)
A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.
A convenient method for lactonization of α-allyl esters using iodine in dimethylsulphoxide
Nawghare, Beena R.,Gaikwad, Sunil V.,Pawar, Bharati V.,Lokhande, Pradeep D.
, p. 469 - 473 (2014/12/11)
A simple method for the synthesis of α-γ-disubstituted-γ-butyrolactones by cyclization of α-allyl esters using iodine in dimethylsulphoxide is reported. This method is efficient and operationally simple in comparison to methods using transition metal comp
Small changes result in large differences: Discovery of (-)-incrustoporin derivatives as novel antiviral and antifungal agents
Lu, Aidang,Wang, Jinjin,Liu, Tengjiao,Han, Jian,Li, Yinhui,Su, Min,Chen, Jianxin,Zhang, Hui,Wang, Lizhong,Wang, Qingmin
, p. 8799 - 8807 (2014/11/08)
On the basis of the structure of natural product (-)-incrustoporin (1), a series of lactone compounds 4a-i and 5a-i were designed and synthesized from nitroolefin. The antiviral and antifungal activities of these compounds were evaluated in vitro and in v
Small changes result in large differences: Discovery of (-)-incrustoporin derivatives as novel antiviral and antifungal agents
Lu, Aidang,Wang, Jinjin,Liu, Tengjiao,Han, Jian,Li, Yinhui,Su, Min,Chen, Jianxin,Zhang, Hui,Wang, Lizhong,Wang, Qingmin
, p. 8799 - 8807 (2015/04/22)
On the basis of the structure of natural product (-)-incrustoporin (1), a series of lactone compounds 4a-i and 5a-i were designed and synthesized from nitroolefin. The antiviral and antifungal activities of these compounds were evaluated in vitro and in v
First iodine-catalyzed deallylation of reactive allyl methylene esters
Nawghare, Beena R.,Lokhande, Pradeep D.
, p. 1955 - 1963 (2013/06/05)
C-Allyl cleavage has been developed using the inexpensive and mild reagent iodine in dimethylsulfoxide. A variety of compounds with active methylene groups were C-deallylated using this reagent. This method is efficient and operationally simple in comparison to the methods using transition-metal complexes. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Isothiourea-catalyzed asymmetric O- to C-carboxyl transfer of furanyl carbonates
Joannesse, Caroline,Morrill, Louis C.,Campbell, Craig D.,Slawin, Alexandra M. Z.,Smith, Andrew D.
, p. 1865 - 1879 (2011/08/05)
The ability of a chiral isothiourea to promote the regio- and enantioselective O- to C-carboxyl transfer of a series of 3-alkyl-5-aryl- and 5-methyl-3-phenylfuranyl carbonates is examined, generating preferentially the -regioisomers (α/γ up to 83:17) with high asymmetric induction (up to 83% ee). Georg Thieme Verlag Stuttgart - New York.
Tellurium in organic synthesis: synthesis of bioactive butenolides
Bassora, Bruno K.,Da Costa, Carlos E.,Gariani, Rogério A.,Comasseto, Jo?o V.,Dos Santos, Alcindo A.
, p. 1485 - 1487 (2008/02/02)
Reduction of (Z)-β-butyltelluro-enones gives the corresponding γ-hydroxy vinylic tellurides with retention of the double bond configuration. Reaction of γ-hydroxy vinylic tellurides with 2 equiv of n-butyllithium produces 1,4-C,O-dianions, which on reaction with carbon dioxide give the corresponding butenolides.
Synthesis and structure-antifungal activity relationships of 3-aryl-5-alkyl-2,5-dihydrofuran-2-ones and their carbanalogues: Further refinement of tentative pharmacophore group
Pour, Milan,Spulak, Marcel,Balsanek, Vojtech,Kunes, Jiri,Kubanova, Petra,Buchta, Vladimir
, p. 2843 - 2866 (2007/10/03)
Two series of 3-(substituted phenyl)-5-alkyl-2,5-dihydrofuran-2-ones related to a natural product, (-)incrustoporine, were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring exhibited selective antifungal activity against the filamentous strains of Absidia corymbifera and Aspergillus fumigatus. On the other hand, the influence of the lenghth of the alkyl chain at C(5) was marginal. The antifungal effect of the most active compound against the above strains was higher than that of ketoconazole, and close to that of amphotericin B. In order to verify the hypothesis about a possible relationship between the Michael-accepting ability of the compounds and their antifungal activity, a series of simple carbanalogues, 2-(substituted phenyl)cyclopent-2-enones, was prepared and subjected to antifungal activity assay as well.
3-Phenyl-5-methyl-2H,5H-furan-2-ones: Tuning antifungal activity by varying substituents on the phenyl ring
Pour, Milan,Spulak, Marcel,Balsanek, Vojtech,Kunes, Jiri,Buchta, Vladimir,Waisser, Karel
, p. 1893 - 1895 (2007/10/03)
A series of racemic 3-phenyl-5-methyl-2H,5H-furan-2-ones related to a natural product, (-)incrustoporine, was synthesized, and their antifungal activity evaluated. The key structural feature, furanone ring, was closed via H2SO4-mediated cyclization of 2-phenylpent-4-enoic acids. The compounds displayed antifungal activity, especially against filamentous fungi. Expressed as the minimum inhibition concentration (MIC) in μmol/L, the activity of the most promising derivative against Absidia corymbifera matched that of ketoconazole (31.25 μmol/L). In terms of μg/mL, the substance was more active (7.6 μg/mL) than this standard antifungal drug (16.6 μg/mL). (C) 2000 Elsevier Science Ltd. All rights reserved.
