- Concise Total Synthesis and Antifungal Activities of Fusaric Acid, a Natural Product
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The total synthesis of a natural product alkaloid fusaric acid (FA), which exhibits herbicide, fungicide, insecticide and even diverse notable pharmacological activities, was accomplished in four steps using commercially available materials. The synthesis, based on a unified and flexible strategy using 6-bromonicotinaldehyde as a common intermediate, is concise, convergent, practical and can be carried out on a two-gram scale. This approach could be readily applicable to the synthesis of its analogues. In addition, FA had a wide range of inhibitory activities against 14 plant pathogenic fungi in this study, which demonstrated that as a leading compound, and it has great potential to be further developed as an agricultural fungicide.
- Huang, Bin Bin,Liu, Ya Yi,Zhu, Peng Fei,Jiang, Yi Cheng,Ouyang, Ming-An
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- Fusaric acid and derivatives as novel antimicrobial agents
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The synthesis and screening of several fusaric acid (FA) and analogues against five common clinical pathogens (gram-positive and gram-negative) and in vitro hemolytic activity assay in human red blood cells, for the first time, were reported. The biological results reveal that FA and its analogues exhibited moderate antimicrobial activities. Compounds 2–5 and 7 showed growth inhibitory activity in gram-positive bacteria. Compounds 6 and 9 showed growth inhibitory activity in both gram-positive and gram-negative bacteria. None of the compounds induce hemolysis, which is potent for future drug development on this template. In addition, the structure–activity relationship and docking studies are discussed.
- Thanh, Tung Truong,Quoc, Thang Nguyen,Xuan, Huy Luong
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p. 1689 - 1696
(2020/07/09)
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- Fusaric acid and analogues as Gram-negative bacterial quorum sensing inhibitors
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Taking advantage of microwave-assisted synthesis, efficient and expedite procedures for preparation of a library of fusaric acid and 39 analogues are reported. The fusaric acid analogues were tested in cell-based screening assays for inhibition of the las and rhl quorum sensing system in Pseudomonas aeruginosa and the lux quorum sensing system in Vibrio fischeri. Eight of the 40 compounds in the library including fusaric acid inhibited lux quorum sensing and one compound inhibited activity of the las quorum sensing system. To our delight, none of the compounds showed growth inhibitory effects in the tested concentration ranges.
- Tung, Truong Thanh,Jakobsen, Tim Holm,Dao, Trong Tuan,Fuglsang, Anja Thoe,Givskov, Michael,Christensen, S?ren Br?gger,Nielsen, John
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p. 1011 - 1020
(2016/12/30)
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- Synthesis of substituted pyridines via regiocontrolled [4 + 2] cycloadditions of oximinosulfonates
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Diels-Alder cycloadditions of oximinosulfonate 8 with a variety of 1, 3-dienes proceed with regiochemistry opposite to that observed with conventional imino dienophiles, providing expeditious synthetic routes to substituted pyridines, tetrahydropyridines, and pyrrolines. The oximinosulfonate 8 is prepared in one convenient synthetic operation from Meldrum's acid and reacts with conjugated dienes at -78 C in the presence of 2 equiv of dimethylaluminum chloride to afford [4 + 2] cycloadducts in good to excellent yield. Exposure of these cycloadducts to the action of NaOMe and JV-chlorosuccinimide in methanol-THF at room temperature then produces substituted pyridines. The utility of this new two-step annulation protocol is demonstrated in total syntheses of the pyridine alkaloids fusaric acid and (S)-(+)-fusarinolic acid. Heating the [4 + 2] cycloadducts derived from 8 in a mixture of acetonitrile and pH 7 phosphate buffer induces an unusual Stieglitztype rearrangement leading to the formation of interesting spirobicyclic pyrrolines.
- Renslo, Adam R.,Danheiser, Rick L.
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p. 7840 - 7850
(2007/10/03)
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- CARBON FUNCTIONALIZATIONS ON PYRIDINE RING VIA TRIMETHYLSTANNYL DERIVATIVES---AN EXAMPLE OF FUSARIC ACID SYNTHESIS---
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Method for introduction of two types of carbon functional groups, acyl and tert-butoxycarbonyl groups, in pyridine ring via bis(trimethylstannyl)pyridine (1) is explored.Application of this method to the synthesis of fusaric acid (1) is also described.
- Yamamoto, Yutaka,Tanaka, Takuo,Ouchi, Hidekazu,Miyakawa, Masayo,Morita, Yasuo
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p. 817 - 826
(2007/10/02)
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- DIELS-ALDER REACTION OF 1,2,3-TRIAZINE WITH ALDEHYDE ENAMINE
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The Diels-Alder reaction of 4-methyl-1,2,3-triazine with several aldehyde enamines was carried out to afford 2,5-disubstituted pyridines.As an application of this method, we accomplished the synthesis of alkaloid, fusaric acid.
- Koyama, Junko,Ogura, Tamaki,Tagahara, Kiyoshi
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p. 1595 - 1600
(2007/10/02)
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- A SHORT SYNTHESIS OF FUSARIC ACID AND ANALOGUES
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Fusaric acid (5-n-butyl-pyridine-2-carboxylic acid) and other substituted picolinic acid derivatives aresynthesiyed in two steps from readily avaliable α,β/unsaturated hzdrazones and 2-chloroacrylonitrile in high yield.
- Waldner, Adrian
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p. 2371 - 2374
(2007/10/02)
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- A New Simple Synthesis of Fusaric Acid and Other 5-Alkyl-2-pyridinecarboxylic Acids
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Carboxamido groups are introduced into the 6-position of 3-acylpyridines with high regioselectivity via Minisci reaction with formamides, Fe(II) sulfate and tert-butyl hydroperoxide.The isolation procedure is considerably improved by the addition of citric acid for complexation of the Fe ions.Fusaric acid and other 5-alkyl-2-pyridine carboxylic acids are obtained by a following Wolff-Kishner reaction in 20-75percent overall yield.
- Langhals, Elke,Langhals, Heinz,Ruechardt, Christoph
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p. 930 - 949
(2007/10/02)
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