134653-72-8Relevant academic research and scientific papers
Reappraising the structures and distribution of metabolites from black aspergilli containing uncommon 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H) -one systems
Henrikson, Jon C.,Ellis, Trevor K.,King, Jarrod B.,Cichewicz, Robert H.
supporting information; experimental part, p. 1959 - 1964 (2011/11/07)
To date, natural products containing 2-benzyl-4H-pyran-4-one and 2-benzylpyridin-4(1H)-one substructures have been encountered in relatively few fungi outside of the black aspergilli clade. While exploring the occurrence of these compounds among Aspergillus spp., it was determined that the structures of the unusual furopyrrols tensidols A and B (5 and 6) and JBIR-86 and JBIR-87 (9 and 10) were incorrect and should be reassigned as 2-benzyl-4H-pyran-4-ones (7, 8, 11e, and 12, respectively). The origin of the unique N-phenyl groups in the 2-benzylpyridin-4(1H)-ones nygerones A and B (1 and 2) were also examined, and it was established that N-phenylamides added to the culture medium were suitable substrates for generating these metabolites; however, this phenomenon remained limited to a single fungus in our collection (Aspergillus niger ATCC 1015). A variety of 2-benzyl-4H-pyran-4-ones and 2-benzylpyridin-4(1H)-ones were detected among the black aspergilli, but only pestalamide B (13) was found in all 11 of the tested strains. These metabolites, as well as a group of synthetic analogues, demonstrated weak antifungal activity against several Candida strains, Aspergillus flavus, and Aspergillus fumigatus.
1,4 DIHYDROPYRIDINE DERIVATIVES AND THEIR USES
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Page/Page column 32, (2010/12/18)
The present invention relates to 1,4-dihydropyridine derivatives of the formula (I) and their uses in the treatment and/or prevention of diseases and disorders directly or indirectly associated with the modification (increase or decrease) of the activity
4-oxo-1,4-dihydropyridines as selective CB2 cannabinoid receptor ligands: Structural insights into the design of a novel inverse agonist series
El Bakali, Jamal,Muccioli, Giulio G.,Renault, Nicolas,Pradal, Delphine,Body-Malapel, Mathilde,Djouina, Madjid,Hamtiaux, Laurie,Andrzejak, Virginie,Desreumaux, Pierre,Chavatte, Philippe,Lambert, Didier M.,Millet, Régis
scheme or table, p. 7918 - 7931 (2011/03/19)
Growing evidence shows that CB2 receptor is an attractive therapeutic target. Starting from a series of 4-oxo-1,4-dihydroquinoline-3- carboxamide as selective CB2 agonists, we describe here the medicinal chemistry approach leading to
Generation and in Situ Acylation of Enaminone Anions: A Convenient Synthesis of 3-Carbethoxy-4(1H)-pyridinones and -4-pyrones and Related Compounds
McCombie, Stuart W.,Metz, William A.,Nazareno, Dennis,Shankar, Bandarpalle B.,Tagat, Jayaram
, p. 4963 - 4967 (2007/10/02)
Treatment of 2--3-oxobutanoates 9 or 10 with LiN(SiMe3)2 in the presence of RCOCl results in C-acylation.The resulting intermediate, without isolation, may be converted to 6-R 3-Carbethoxy-4-pyrones (e.g., 12) by H3O+ or to the corresponding pyridinones (e.g., 13) by NH4OAc.Typically, yields are 55-75percent for R groups lacking acidic α or γ protons and ca. 30percent for R = Me2CH or MeCH=CH.Replacing 9 with MeCOC(=CHNMe2)SCH2Ph (from MeCOCH2SCH2Ph and Me2NCH(OMe)2 similarly affords 3-(PhCH2S)-substituted products such as 29.Alkylation of the pyridinone anions produces mixtures of N- and O-substituted compounds, with the latter predominating; aminolysis of the isolated pyrones (R'NH2-HOAc, where R' = alkyl, Ar, HO, etc.) is the preferred route to the 1-R'-substituted pyridinones.
