- 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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- Novel cytokine production inhibitors produced by a basidiomycete, Marasmiellus sp.
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New cytokine production inhibitors, CJ-14,877 (I) and CJ-14,897 (II), were isolated from the fermentation broth of a basidiomycete, Marasmiellus sp. CL21624. Their structures were determined to be methyl-(7R,8S)-5-(7,8-dihydroxypropyl)pyridine-2-carboxylate and methyl-(7R,8S)-5-(8-acetoxy-7-hydroxyprophyl)pyridine-2-carboxylate, respectively, by spectroscopic analyses. These compounds showed inhibitory activities for lipopolysaccharide-induced production of interleukin-1β and tumor necrosis factor-α in human whole blood with IC50 values of the range from 0.059 to 2.6 μM.
- Ichikawa,Hirai,Ishiguro,Kambara,Kato,Kim,Kojima,Matsunaga,Nishida,Shiomi,Yoshikawa,Kojima
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- Fusaric and 9,10-dehydrofusaric acids and their methyl esters from Fusarium nygamai
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Fusaric and 9,10-dehydrofusaric acids and their corresponding methyl esters were isolated from the culture filtrates of Fusarium nygamai. The methyl esters were characterized by chemical and spectroscopic methods and reported here for the first time as naturally occurring products. When assayed on tomato leaves and seedlings at 2.7 × 10-3 and 2 × 10-4 M, respectively, fusaric and 9,10-dehydrofusaric acids and their methyl esters showed wide chlorosis rapidly evolving into necrosis as well as a strong inhibition of root elongation, respectively. When assayed at 10-4 M on brine shrimps (Artemia salina), fusaric and 9,10-dehydrofusaric acids did not prove to be toxic, while their methyl esters showed a toxicity level of 50%, expressed as mortality. Copyright
- Capasso, Renato,Evidente, Antonio,Cutignano, Adele,Vurro, Maurizio,Zonno, Maria Chiara,Bottalico, Antonio
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- Renal-selective prodrugs for control of renal sympathetic nerve activity in the treatment of hypertension
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Renal-selective prodrugs are described which are preferentially converted in the kidney to compounds capable of inhibiting synthesis of catecholamine-type neurotransmitters involved in renal sympathetic nerve activity. The prodrugs described herein are de
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Page/Page column 100-101
(2010/11/30)
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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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