- Design and synthesis of chitin synthase inhibitors as potent fungicides
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Chitin is a structural component of fungal cell walls but is absent in vertebrates, mammals, and humans. Chitin synthase is thus an attractive molecular target for developing fungicides. Based on the structure of its donor substrate, UDP-N-acetyl-glucosamine, as well as the modelled structure of the bacterial chitin synthase NodC, we designed a novel scaffold which was then further optimized into a series of chitin synthase inhibitors. The most potent inhibitor, compound 13, exhibited high chitin synthase inhibitory activity with an IC50 value of 64.5?μmol/L. All of the inhibitors exhibited antifungal activities against the growth of agriculturally-destructive fungi, Fusarium graminearum, Botrytis cinerea, and Colletotrichum lagenarium. This work presents a new scaffold which can be used for the development of novel fungicides.
- Chen, Qi,Zhang, Ji-Wei,Chen, Lu-Lu,Yang, Jun,Yang, Xin-Ling,Ling, Yun,Yang, Qing
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p. 1232 - 1237
(2017/06/19)
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- Synthesis of α,β-unsaturated aldehydes based on a one-pot phase-switch dehydrogenative cross-coupling of primary alcohols
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An efficient one-pot ruthenium-catalyzed hydrogen-transfer strategy for a direct access to α,β-unsaturated aldehydes has been developed. The employment of enolates prepared in situ from alcohols avoided handling unstable aldehydes and provided a very appealing route to different cinnamaldehydes substituted in position 2. A silica-grafted amine was used as phase-switch tag leading to a selective one-pot process in favor of cross-dehydrogenative coupling products.
- Mura, Manuel G.,De Luca, Lidia,Taddei, Maurizio,Williams, Jonathan M. J.,Porcheddu, Andrea
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supporting information
p. 2586 - 2589
(2014/06/09)
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- Microwave-assisted organocatalytic cross-aldol condensation of aldehydes
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An environmentally benign organocatalytic cross-aldol condensation of aldehydes under microwave irradiation in the absence of solvent is described. Using pyrrolidine as a catalyst, an efficient and sustainable atom economic method was developed for the cross-aldol condensation of various aldehydes with excellent results. Among the products, jasmine aldehyde, α-hexyl cinnamaldehyde and cyclamen aldehyde, three compounds of great industrial demand, were synthesised.
- Limnios, Dimitris,Kokotos, Christoforos G.
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p. 4496 - 4499
(2013/05/09)
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- Highly selective aldol condensation using amine-functionalized SiO2-Al2O3 mixed-oxide under solvent-free condition
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A series of amine catalysts supported on mesoporous molecular sieves SiO2/Al2O3 with trimethoxysilylpropylamine [(CH3O)3Si(CH2)3NH2] loading varying from 3 mmol to 6 mmol were synthesized by impregnation method. The aldol condensation of various aromatic aldehydes and 1-heptanal was used to test the acid-base cooperativity of amine-functionalized SiO2/Al2O3. The effects of solvent, reaction temperature, benzaldehyde to 1-heptanal molar ratio, different supports (SiO2, Al2O3 and SiO2-Al2O3), catalyst amount and recyclability of the catalyst were investigated. Sample containing 5 mmol amine loaded showed highest benzaldehyde conversion (100%) and selectivity (97%) for jasminaldehyde.
- Abbaspourrad, Alireza,Javad Kalbasi, Roozbeh,Zamani, Farzad
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experimental part
p. 2074 - 2082
(2011/06/19)
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- A general route to α-alkyl (E)-α,β-unsaturated aldehydes
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Bis(trimethylsilyl)-tert-butylaldimines 3 react with aldehydes in the presence of zinc bromide at room temperature to give, after hydrolysis, the desired α-alkyl α,β-ethylenic aldehydes in good yield and with very high E stereoselectivity. The reaction was believed to proceed via the α-silyl β-siloxyimines 4.
- Lahmar, Nour,Aatar, Jamaa,Ayed, Ta?cir Ben,Amri, Hassen,Bellassoued, Moncef
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p. 3018 - 3026
(2007/10/03)
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- An Improved Synthesis of α-n-Amylcinnamaldehyde Based on Liquid Phase Transfer
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α-n-Amylcinnamaldehyde is synthesized by the condensation of benzaldehyde with n-heptanal using anhydrous potassium carbonate and benzyltriethylammonium chloride as a phase transfer catalyst in dichloromethane.This method is superior to other methods with regard to yield which is ca. 80 percent.Two other substituted α-n-amylcinnamaldehydes have also been obtained by a similar procedure.
- Sarkar, A.,Dey, P. K.,Datta, K.
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