Design, synthesis, and fungicidal activity of novel carboxylic acid amides represented by N-benzhydryl valinamode carbamates

Du, Xiu‐Jiang; Bian, Qiang; Wang, Hongxue; Yu, Shujing; Kou, Junjie; Wang, Zhipeng; Li, Zhengming; Zhao, Wei‐Guang

doi:10.1039/c4ob00744a

Cited by 28 publications

(17 citation statements)

References 17 publications

(19 reference statements)

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“…First, we transformed the previously obtained coumarin 3 into acyl chloride, which we wanted to react with the amino group of CoumMono . We used dimethylaminopyridine as catalyst and triethylamine as base, but these conditions turned out to be ineffective . The method involving the formation of an active complex and subsequent coupling with amine also did not give the desired product .…”

Section: Resultsmentioning

confidence: 99%

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Kielesiński

Morawski

Sobolewski

et al. 2017

Chemistry A European J

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The synthesis of a weakly coupled, strongly polarized coumarin dimer has been achieved for the first time. The three-step strategy comprises the Skattebøl formylation followed by the Knoevenagel reaction and the formation of a tertiary amide by using a peptide-type procedure. The molecule consists of two different coumarin moieties: One is a classical donor-acceptor system and the second one possesses a weaker amide donor at the 7-position. The polarized coumarin dimer can form an electronically conjugated structure possessing an electric dipole larger than that of 7-(dimethylamino)coumarin-3-carboxylic acid. The limited flexibility of the inter-coumarin connection results in stable conformers of different electric dipole moments and complex photophysics. In the solid state, this compound has a strongly bent conformation with the two coumarin units forming an angle of around 74°. In solution, two conformers are in equilibrium. The existence of the molecule as two conformers in the ground state has been confirmed by optical studies, and further corroborated by molecular calculations. The fluorescence spectra possess a unique feature: A charge-transfer band (ca. 550 nm) is visible only in nonpolar or weakly polar solvents. Optical spectroscopy studies coupled with molecular calculations allowed us to rationalize this phenomenon: The large amplitude of intramolecular motions is responsible for the conformational isomerization as well as producing a conical intersection between the potential energy surfaces of the excited singlet state and the ground state, which opens an internal conversion channel that effectively competes with the fluorescence of the conformers.

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Section: Resultsmentioning

confidence: 99%

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Kielesiński

Morawski

Sobolewski

et al. 2017

Chemistry A European J

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“…Traditionally, fragment hits were often found by conventional bioassay-based methods and biophysical methods (X-ray, NMR and surface plasmon resonance). However, in our previous work [36][37][38][39] , we find that three sub-classes fungicides have nearly identical structural fragments: including amide, halobenzene (or methylbenzene) and/or dialkoxyl benzene. The three fragments are exactly what we are looking for fragments with a good match with a target binding site, because any optimisation of the three fragments could lead to reduced antifungal activity.…”

Section: Resultsmentioning

confidence: 80%

Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model

Peng

Zhao

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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2020) Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model, Journal of Enzyme Inhibition and Medicinal Chemistry, 35:1, 682-691, ABSTRACTThirty-six novel threoninamide carbamate derivatives were designed and synthesised using active fragment-based pharmacophore model. Antifungal activities of these compounds were tested against Oomycete fungi Phytophthora capsici in vitro and in vivo. Interestingly, compound I-1, I-2, I-3, I-6 and I-7 exhibited moderate control effect (>50%) against Pseudoperonospora cubensis in greenhouse at 6.25 lg/ mL, which is better than that of control. Meanwhile most of these compounds exhibited significant inhibitory against P. capsici. The other nine fungi were also tested. More importantly, some compounds exhibited remarkably high activities against Sclerotinia sclerotiorum, P. piricola and R. solan in vitro with EC 50 values of 3.74-9.76 lg/mL. It is possible that the model is reliabile and this method can be used to discover lead compounds for the development of fungicides. ARTICLE HISTORY

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“…[9][10][11][12][13][14] We have previously reported the synthesis of, and evaluated the fungicidal activities of a series of mandelic acid amide and valinamide carbamate derivatives. 19 Compound 1a displayed higher in vitro fungicidal activities against Phytophthora capsici (EC 50 0.15 µg mL −1 ) than iprovalicarb (EC 50 0.27 µg mL −1 ). Therefore, we designed and synthesized novel valinamide carbamate with all three fragments.…”

Section: Introductionmentioning

confidence: 97%

Design, synthesis and antifungal activity of carboxylic acid amide fungicides: part 2: substituted 1-phenyl-2-phenoxyethylamino valinamide carbamates

et al. 2015

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Most of the "stretched" valinamide carbamates analogues had higher antioomycetic potency than dimethomorph. The field trial showed that 8b is a promising candidate for future development.Valinamide carbamates are important agricultural fungicides with anti-oomycete activity and low toxicity toward mammalian cells. To find valinamide carbamates with high activity against resistant pathogens, a series of substituted 1phenyl-2-phenoxyethylamino derivatives were designed and synthesized by introducing substituted phenyloxy or benzyloxy into valinamide carbamate leads. Bioassays showed that many title compounds exhibited good anti-oomycete activity. Compound 8b had much higher in vitro fungicidal activity against Phytophthora capsici than the control compound iprovalicarb and had a similar potency to the control mandipropamid. At 6.25 µg mL −1 the fungicidal activities of many compounds against in vivo Pseudoperonospora cubensis were greater than 30%, while the control dimethomorph gave only 27% activity at this concentration. The effect of 8b against Pseudoperonospora cubensis in the field indicates promise for a new candidate for controlling cucumber downy mildew. Results and discussionChemistry

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Design, synthesis, and fungicidal activity of novel carboxylic acid amides represented by N-benzhydryl valinamode carbamates

Cited by 28 publications

References 17 publications

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

The Coumarin‐Dimer Spring—The Struggle between Charge Transfer and Steric Interactions

Design, synthesis and antifungal activity of threoninamide carbamate derivatives via pharmacophore model

Design, synthesis and antifungal activity of carboxylic acid amide fungicides: part 2: substituted 1-phenyl-2-phenoxyethylamino valinamide carbamates

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