Detour of prenostodione synthesis towards pyrazolones for antibacterial activity

Our attempts to prepare indolyl acid (3), enroute to prenostodione (2), from phenyl-hydrazine following a reported procedure of Fischer-Indole synthesis rather lead to ethyl 2-(5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-3-yl)acetate as a major product, which underwent facile condensation with aldehydes t...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2013-06, Vol.23 (11), p.3235-3238
Hauptverfasser: Rasapalli, Sivappa, Fan, Yingjun, Yu, Menglong, Rees, Christiaan, Harris, John T., Golen, James A., Jasinski, Jerry P., Rheingold, Arnold L., Kwasny, Steven M., Opperman, Timothy J.
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Sprache:eng
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Zusammenfassung:Our attempts to prepare indolyl acid (3), enroute to prenostodione (2), from phenyl-hydrazine following a reported procedure of Fischer-Indole synthesis rather lead to ethyl 2-(5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-3-yl)acetate as a major product, which underwent facile condensation with aldehydes to provide the pyrazolones. Intrigued by the opportunity for the diversity oriented synthesis of substituted pyrazolones, we have developed a facile one pot approach for pyrazolones and screened for antibacterial activity and, herein, results are reported.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2013.03.123