- Synthesis and QSAR study of novel α-methylene-γ-butyrolactone derivatives as antifungal agents
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Thirty-six new α-benzylidene-γ-lactone compounds based α-methylene-γ-butyrolactone substructure were prepared and characterized by spectroscopic analysis. All compounds were evaluated for antifungal activities in vitro against six plant pathogenic fungi and the half maximal inhibitory concentration (IC50) against Botrytis cinerea and Colletotrichum lagenarium were investigated. Compounds 5c-3 and 5c-5 with the halogen atom exhibited excellent fungicidal activity against B. cinerea (IC50?=?22.91, 18.89?μM). The structure-activity relationships (SARs) analysis indicated that the derivatives with electron-withdrawing substituents at the meta- or para-positions improves the activity. Via the heuristic method, the generated quantitative structure-activity relationship (QSAR) model (R2?=?0.961) revealed a strong correlation of antifungal activity against B. cinerea with molecular structures of these compounds. Meanwhile, the cytotoxicity of 20 representative derivatives was tested in the human tumor cells line (HepG2) and the hepatic L02 cells line, the result indicated that the synthesized compounds showed significant inhibitory activity and limited selectivity. Compound 5c-5 has the highest fungicidal activity with IC50?=?18.89?μM (against B. cinerea.) but low cytotoxicity with IC50?=?35.4?μM (against HepG2 cell line) and IC50?=?68.8?μM (against Hepatic L02 cell line). These encouraging results can be providing an alternative, promising use of α-benzylidene-γ-lactone through the design and exploration of eco-friendly fungicides with low toxicity and high efficiency.
- Wu, Yong-Ling,Wang, De-Long,Guo, En-Hui,Song, Shuang,Feng, Jun-Tao,Zhang, Xing
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supporting information
p. 1284 - 1290
(2017/06/19)
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- New antifungal scaffold derived from a natural pharmacophore: Synthesis of α-methylene-γ-butyrolactone derivatives and their antifungal activity against Colletotrichum lagenarium
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Thirty new and thirty-four known analogues were designed and synthesized to improve the potential use of the α-methylene-γ-butyrolactone ring, a natural pharmacophore. All structures were confirmed by 1H and 13C NMR, MS, and single-c
- Jun-Tao, Feng,De-Long, Wang,Yong-Ling, Wu,He, Yan,Xing, Zhang
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supporting information
p. 4393 - 4397
(2013/07/26)
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- Fluorous tagging: An enabling isolation technique for indium-mediated allylation reactions in water
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An efficient method was developed to allylate aldehydes using an aqueous indium-mediated allylation reaction with fluorous-tagged allyl halides, and to directly purify the products by fluorous solid phase extraction (F-SPE). The Royal Society of Chemistry
- Reid, Carolyn S.,Zhang, Yuhua,Li, Chao-Jun
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p. 3589 - 3591
(2008/09/21)
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- Titanocene(III) chloride mediated radical-induced one-pot synthesis of α-methylene-γ-butyrolactones
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A simple and efficient methodology has been developed for the one-pot preparation of α-methylene-γ-butyrolactones by free-radical induced Barbier-type reaction of methyl 2-(bromomethyl)acrylate and aldehydes followed by in situ lactonization. The radical
- Paira, Moumita,Banerjee, Biplab,Jana, Samaresh,Mandal, Samir Kumar,Roy, Subhas Chandra
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p. 3205 - 3207
(2007/10/03)
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- Synthesis of (E)- and (Z)-α-alkylidene-γ-aryl-γ- butyrolactones via alkenylalumination of oxiranes
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(Chemical Equation Presented) Alkenylalumination of substituted styrene oxides with [α-(ethoxycarbonyl)alkenyl]diisobutylaluminum, in the presence of BF3·Et2O, affords the corresponding (Z)-α-alkylidene-γ-aryl-γ-hydroxy esters in 81-
- Ramachandran, P. Veeraraghavan,Garner, Garrett,Pratihar, Debarshi
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p. 4753 - 4756
(2008/03/14)
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- Preparation of Chiral β-Functionalized Allylboronate Reagents and their Application to Asymmetric Synthesis of α-methylene-γ-lactams and and γ-lactones
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Various chiral β-functionalized allylboronates are prepared by alkylation of α-functional vinylaluminium reagents with chiral α-chloromethylboronates with excellent yields and high regioselectivity.The ability of these new chiral allylboronates to afford the expected α-methylene-γ-lactams and γ-lactones on treatment with imines and aldehydes is also reported. - Keywords: chiral chloromethylboronate; vicinal diol; chiral β-functionalized allylboronate; α-methylene-γ-lactam; α-methylene-γ-lactone.
- Nyzam, Valerie,Belaud, Chantal,Zammattio, Francoise,Villieras, Jean
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p. 583 - 592
(2007/10/03)
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- Lead-promoted 2-carboethoxyallylation or 2-carboxylallylation of aldehydes: A new and facile method for the synthesis of α-methylene-γ-butyroactones
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In the presence of powdered lead, the reaction of aldehydes and α-bromomethylacrylate (or α-bromomethylacrylic acid) can be carried out under mild condition, the products 4-hydroxy-2-methylenebutanoates (or 4-hydroxy-2-methylenebutanoic acids) can be easi
- Zhou,Jia,Yao,Wu
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p. 2397 - 2406
(2007/10/03)
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- Electrogenerated Zinc as the Catalyst in the Allylation of Carbonyl Compounds. Direct Synthesis of α-Methylene-γ-Lactones
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The electroreduction of a catalytic amount of ZnBr2 in acetonitrile provided a active Zn*, able to catalyze the reductive coupling of allyl bromides and chlorides with carbonyl compounds with high regioselectivity.Substituted α-methylene γ-lactones were o
- Rollin, Y.,Derien, S.,Dunach, E.,Gebehenne, C.,Perichon, J.
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p. 7723 - 7732
(2007/10/02)
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- An SnCl2-Promoted α-Methylene-γ-butirolactone Synthesis in an Aqueous Medium
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Reaction of α-bromomethylacrylic acid with aldehydes in an SnCl2-MeOCH2CH2OH-H2O system provides γ-substituted-α-methylene-γ-butirolactones.
- Uneyema, Kenji,Ueda, Kunimasa,Torii, Sigeru
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p. 1201 - 1202
(2007/10/02)
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- Asymmetric Synthesis of α-Methylene-γ-butyrolactones Using Chiral N-Monosubstituted 2-propenamides
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α-Methylene-γ-butyrolactones were prepared in high yields on treatment of N-monosubstituted 2-propenamides with aldehydes in the presence of a Lewis acid followed by acidic hydrolysis of the resulting γ-hydroxy amides.Asymmetric synthesis of α-methylene-γ-butyrolactones was investigated by using a variety of chiral 2-propenamides derived from optically active amines.Reaction of N--2-propenamide or its antipode with aldehydes in the presence of 4 equiv of TiCl4 gave, after hydrolysis, α-methylene lactones in an enantiometric excess of as high as 80percent.Optically pure 3-methylene-2-pyrrolidinones were obtained in excellent yields by a one-pot sequence starting with the γ-hydroxy amides.
- Tanaka, Kazuhiko,Yoda, Hidemi,Isobe, Yutaka,Kaji, Aritsune
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p. 1856 - 1866
(2007/10/02)
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