- Design, synthesis and antifungal activity of novel fenfuram-diarylamine hybrids
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Ten novel fenfuram-diarylamine hybrids were designed and synthesized. And their antifungal activities against four phytopathogenic fungi have been evaluated in vitro and most of the compounds demonstrated a significant antifungal activities against Rhizoctonia solani and Sclerotinia sclerotiorum. Compound 5e exhibited the most potent antifungal activity against R. solani with an EC50value of 0.037 mg/L, far superior to the commercially available fungicide boscalid (EC50= 1.71 mg/L) and lead fungicide fenfuram (EC50= 6.18 mg/L). Furthermore, scanning electron microscopy images showed that the mycelia on treated media grew abnormally with tenuous, wizened and overlapping colonies compared to the negative control. Molecular docking studies revealed that compound 5e featured a higher affinity for succinate dehydrogenase (SDH) than fenfuram. Furthermore, it was shown that the 3-chlorophenyl group in compound 5e formed a CH-π interaction with B/Trp-206 and a Cl-π interaction with D/Tyr-128, rendering compound 5e more active than fenfuram against SDH.
- Wang, Hongyu,Gao, Xuheng,Zhang, Xiaoxiao,Jin, Hong,Tao, Ke,Hou, Taiping
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supporting information
p. 90 - 93
(2016/12/09)
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- Discovery of potent inhibitors of Schistosoma mansoni NAD+ catabolizing enzyme
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The blood fluke Schistosoma mansoni is the causative agent of the intestinal form of schistosomiasis (or bilharzia). Emergence of Schistosoma mansoni with reduced sensitivity to praziquantel, the drug currently used to treat this neglected disease, has underlined the need for development of new strategies to control schistosomiasis. Our ability to screen drug libraries for antischistosomal compounds has been hampered by the lack of validated S. mansoni targets. In the present work, we describe a virtual screening approach to identify inhibitors of S. mansoni NAD+ catabolizing enzyme (SmNACE), a receptor enzyme suspected to be involved in immune evasion by the parasite at the adult stage. Docking of commercial libraries into a homology model of the enzyme has led to the discovery of two in vitro micromolar inhibitors. Further structure-activity relationship studies have allowed a 3-log gain in potency, accompanied by a largely enhanced selectivity for the parasitic enzyme over the human homologue CD38.
- Jacques, Sylvain A.,Kuhn, Isabelle,Koniev, Oleksandr,Schuber, Francis,Lund, Frances E.,Wagner, Alain,Muller-Steffner, Héleìne,Kellenberger, Esther
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p. 3582 - 3592
(2015/05/05)
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- Anti-viral aromatic hydrazones
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Compounds of the formula STR1 wherein Q is a hydrazone derivative; R1 is hydrogen, halogen, alkyl or alkoxy; R2 is hydrogen, halogen, alkyl, alkoxy, alkenoxy, alkynyloxy, halomethyl, trifluoromethoxy, alkylthio, nitro or cyano; and R
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- The Birch Reduction of Heterocyclic Compounds. III. [1] Birch Reduction-Elimination Reaction of 2- and 3-Furancarboxylic Acid Derivatives
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The Birch reduction of 2-(1-alkoxyalkyl)furan-3-carboxylic acids la-f gave 2-alkyl-3-furancarboxylic acids 2a-f with loss of the alkoxyl group in excellent isolated yields.
- Ohta, Yasuo,Onoshima, Mari,Tamura, Masumi,Tanaka, Rika,Morimoto, Yoshiki,Yoshihara, Kazuo,Kinoshita, Takamasa
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p. 461 - 465
(2007/10/03)
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- Phosphorylamides, their preparation and use
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A phosphorylamide derivative represented by the general formula (I): STR1 wherein R represents an amino group that may be substituted, or a salt thereof, possesses potent antibacterial activity against Helicobacter bacterium, especially Helicobacter pylori, and is useful for prevention or treatment of digestive diseases caused by Helicobacter bacterium, solely or in combination with an antacid or an acid secretion inhibitor.
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- Facile strategy to 3-acylfurans by silver(I)/celite-mediated cycloaddition of 1,3-dicarbonyl compounds to vinyl sulfides. First total synthesis of α-clausenan
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An efficient synthesis of 3-acylfurans is achieved by silver((I)/Celite-mediated cycloaddition of dicarbonyl compounds, with vinyl sulfides.
- Lee Yong Rok, R.,Kim, Nam Suk,Kim, Byung So
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p. 5671 - 5674
(2007/10/03)
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- Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 2. Regioselective Lithiation of 2-Silylated-3-substituted Furan Rings
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A new method for the preparation of 3,4- and 2,5-disubstituted furan rings is described. A variety of 2-silylated-3-(hydroxymethyl)furans and 2-silylated-3-furoic acids lithiate exclusively at C-4 when treated with 2.2 equivs of BuLi. The resulting dianions were quenched with a variety of electrophiles to provide 2-silylated-3-(hydroxymethyl)-4-substituted furans and 2-silylated-4-substituted 3-furoic acids in good to excellent yields. Removal of the silyl group (n-Bu4NF) provided a variety of 4-substituted-3-(hydroxymethyl)furans and methyl 4-substituted-3-furoates, respectively. The latter esters were prepared due to difficulties encountered in isolating 4-substituted-3-furoic acids. The site of lithiation was altered by protecting the 3-hydroxyl group with a triethylsilane. Lithiation of 2-silylated-3-(((triethylsilyl)oxy)methyl)furan with 1.2 equivs of BuLi followed by the addition of electrophiles provided 2-silylated-3-(((triethylsilyl)oxy)methyl)-5-substituted furan rings. Subsequent removal of both silyl groups provided 2,4-disubstituted furan rings in moderate to good yields. A rationale is provided to explain why protection of the hydroxyl group at C-3 leads to a change in lithiation from the C-4 to the C-5 position of the furan ring. In addition, an explanation for the observed effect of adding HMPA or LiCl to the solution during the lithiation of 2-(tert-butyldimethylsilyl)-3-(hydroxymethyl)furan is provided.
- Bures, Edward,Nieman, James A.,Yu, Shuyuan,Spinazzé, Patrick G.,Bontront, Jean-Louis J.,Hunt, Ian R.,Rauk, Arvi,Keay, Brian A.
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p. 8750 - 8759
(2007/10/03)
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- Effects of α-tert-Butyl Group Substitution on the Reactivity and Dimerization Products of Furan-Based o-Quinodimethanes
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Flash vacuum pyrolysis (FVP) of 2-neopentyl-3-furylmethyl benzoate (8) produces 3-methylene-2-(tert-butylmethylene)-2,3-dihydrofuran (5), the major product as shown by low-temperature 1H NMR spectroscopy.Upon warming to room temperature, 5 dimerizes giving mostly two stereoisomeric dimers 11a and 11b in addition to a small amount of the dimer 12.FVP of a mixture of the two dimers 11a and 11b gives the thermodynamically more stable dimer 12.The rate constants for the dimerization of 5 in solution at temperatures from -29 to +5 deg C were determined by 1H NMR spectroscopy.The rate constants and activation parameters (ΔH(excit.) = 10.8 kcal/mol, ΔS(excit.) = -28.8 eu) are very similar to those reported for the unsubstituted furan-based o-quinodimethane.FVP of (2-methyl-3-furyl)(tert-butyl)methyl benzoate (13) and (2-neopentyl-3-furyl)(tert-butyl)methyl benzoate (18) give as the major product, 2-methylene-3-(tert-butylmethylene)-2,3-dihydrofuran (6) and 2,3-bis(tert-butylmethylene)-2,3-dihydrofuran (7), respectively.Compunds 6 and 7, in contrast to 5, are stable at room temperature apparently because for each of these compounds a bulky tert-butyl group is on the more reactive methylene, the 3-methylene.These results offer further support for the mechanism for the dimerization of furan-based o-quinodimethanes which proceeds in two steps via a transient diradical intemediate.
- Trahanovsky, Walter S.,Huang, Yih-chuan Jason,Leung, Man-kit
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p. 2594 - 2598
(2007/10/02)
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- Unsaturated Sulfoxides in Organic Synthesis: A New General Furan Synthesis
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Furans have been efficiently synthesised by a three-step reaction sequence.Michael addition of keto esters to alkenyl sulfoxides followed by Pummerer rearrangement afforded the cyclic intermediates 11 in good yield.Treatment of the latter with 3-chloroperoxybenzoic acid led by oxidation and syn-elimination of the corresponding sulfoxide, to substituted furans.
- Chan, Wing Hong,Lee, Albert W. M.,Chan, Eddy T. T.
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p. 945 - 946
(2007/10/02)
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- The Regiospecific C-4 Lithiation of 2-(tert-Butyldimethylsilyl)-3-furoic Acid
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2-(tert-Butyldimethylsilyl)-3-furoic acid 7 was regiospecifically lithiated at the C-4 position when treated with 2.5 equiv. of butyllithium (at -20 deg C) in either tetrahydrofuran or 1,2-dimethoxyethane; trapping of the dianion with a variety of electrophiles provided 2,3,4-trisubstituted furans in good to excellent yield.
- Yu, Shuyuan,Keay, Brian A.
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p. 2600 - 2601
(2007/10/02)
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- The Generation and Chemistry of Dianions derived from Furancarboxylic Acids
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Methods for the generation of the dianionic species lithium 5-lithiofuran-2-carboxylate (5) and lithium 2-lithiofuran-3-carboxylate (21) from furan-2- and furan-3-carboxylic acids recpectively are described.The reactions of (5) and (21) with a range of electrophiles have been examined; in general these are very efficient with aldehydes and ketones but not as satisfactory with alkyl halides and epoxides.The dianions do not couple with allylic or benzylic halides, nor with nitriles or orthoesters.The generation of lithium-5-lithio-3-methylfuran-2-carboxylate (15) from 3-methyl furan-2-carboxylic acid is also described; the chemistry of (15) is very similar to (5) derived from furan-2-carboxylic acid.
- Knight, David W.,Nott, Andrew P.
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p. 1125 - 1131
(2007/10/02)
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- Furan-3-carboxamide derivatives and method of preparing same
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A broad class of furan-3-Carboxamide derivatives, including many novel compounds, can be made reliably and in good yields by a novel one step reaction between an α-hydroxyketone and an acetamide in the presence of a Friedel-Crafts agent in an inert solvent. The broad class of derivatives has fungicidal and insecticidal utility.
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