Improved synthesis of quinocetone and its two deoxy metabolites (original) (raw)
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Molecules, 2008
The unexpected substitution of fluorine atoms and phenoxy groups attached to quinoxaline or benzofuroxan rings is described. The synthesis of 2-benzyl-and 2-phenoxy-3-methylquinoxaline 1,4-di-N-oxide derivatives was based on the classical Beirut reaction. The tendency of fluorine atoms linked to quinoxaline or benzofuroxan rings to be replaced by a methoxy group when dissolved in an ammonia saturated solution of methanol was clearly demonstrated. In addition, 2-phenoxyquinoxaline 1,4-di-N-oxide derivatives became 2-aminoquinoxaline 1,4-di-N-oxide derivatives in the presence of gaseous ammonia.
Developments in Quinoline Synthesis: A Review
Quinoline ring structure is obtained by o-condensation of benzene ring with pyridine. It is also called l-azanaphthalene or benzo[b]pyridine. Since first synthesis quinoline, number of methods has been discovered to enhance reaction yield, decrease reaction time as well as reduce hazardous reagents and reaction conditions. Compound with quinoline core are widely used for industrial purposes and also exhibit a broad range of biological activities. An overview of synthetic methodologies used for the construction of quinoline ring is also described.
Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide
A series of 2-acetyl and 2-benzoyl-6(7)-substituted quinoxaline 1,4-di-N -oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. The results show that 2-acetyl-3-methylquinoxaline 1,4-di-N -oxide derivatives with chlorine, methyl or methoxy group in position 7 of the benzene moiety (compounds 2, 4 and 6, respectively) and unsubstituted (3) have good antitubercular activity, exhibiting EC 90 /MIC values between 0.80 and 4.29. In conclusion, the potency, selectivity and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity.
In vitro antioxidant potential study of some synthetic quinoxalines
Bangladesh Medical Research Council bulletin, 2012
In continuation of our study the in vitro antioxidant activity of some novel quinoxaline derivatives was investigated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method with respect to ascorbic acid. To determine the antioxidant activity, a number of substituted indoxyls (3A-G), cyclic ketones (2A-G), and quinoxalines (1A-G) were synthesized by both microwave and conventional heating methods. The present findings revealed that some quinoxalines and their precursors (1D, 1F, 1G and 2E) exhibited a marked scavenging effect on DPPH radical.
Synthesis and Reactions of Quinoxalines
INFLIBNET, 1990
INTRODUCTION 14 yielding 2-D-arabino tetrahydroxybutyl quinoxaline (21). HOAc CH~ Similarly, o-phenylenediamine and dehydro ascorbic acid 15 condense giving 2-hydroxy-3-(11-oxo-2 ' ,3' ,4 '-trihydroxybutyl)quinoxaline (22). 2.2.2 Intramolecular cyclisation reactions Cyclisation of o<.-amino acid intermediates formed from the amino acid and an o-nitrohalogenobenzene is an
Archives of Pharmacal Research, 2011
In this study, twenty-one arylaminoquinoxalinone derivatives were synthesized and their antibacterial activities against Staphylococci aureus, Pseudomonas aureus, Escherichia coli, Bacillus subtilis, Salmonella typhi, and Shigella pneumoniae were evaluated relative to known antibiotics; augmentin, ampicillin, and chloramphenicol. The insecticidal activities of the prepared compounds were also investigated against Tribolium castaneum using permethrin as a standard insecticide. The derivatives were synthesized using both conventional and microwave techniques. Their structures were confirmed using spectral techniques and elemental analysis.
Recent Studies of Antioxidant Quinoline Derivatives
Mini Reviews in Medicinal Chemistry, 2013
Abstrrcti Quinolinc dclivatives constitute an importatrt class of compounds for new drug development. As a large number of experimental and thcorctical rdieshaveshopnahatth€quinolineringsystcmisanimporlantsbucluralunitrridelyexistinginatkaloids,therapeuticsandsynthcticanalogueswithexcitingbiologicalactivities.TheF€sentrcviewprcvidesrecentantioxidardies have shopn ahat th€ quinoline ring systcm is an imporlant sbuclural unit rridely existing in atkaloids, therapeutics and synthctic analogues with exciting biological activities. The F€sent rcview prcvides recent antioxidardieshaveshopnahatth€quinolineringsystcmisanimporlantsbucluralunitrridelyexistinginatkaloids,therapeuticsandsynthcticanalogueswithexcitingbiologicalactivities.TheF€sentrcviewprcvidesrecentantioxidat activities covering in vivo and in ritlo studies of natural and synihetic analogues, as well as the proposad mechanisms of acion and structure-activity relationships.