Synthesis and biological studies of some benzopyrano[2,3-c]pyrazole derivatives

Trkovnik²,

et al. 2006

Molecules

(7-Hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide (2) was prepared from (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester (1) and 100% hydrazine hydrate. Compound 2, is the key intermediate for the synthesis of several series of new compounds such as Schiff's bases 3a-l, formic acid N'-[2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetyl] hydrazide (4), acetic acid N'-[2-(7-hydroxy-2-oxo-2H-chromen-4-yl)-acetyl] hydrazide (5), (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid N'-[2-(4-hydroxy-2-oxo-2H-chromen-3-yl)-2-oxoethyl] hydrazide (6), 4-phenyl-1-(7-hydroxy-2-oxo-2H-chromen-4-acetyl) thiosemicarbazide (7), ethyl 3-{2-[2-(7-hydroxy-2-oxo-2H-chromen-4-yl)-acetyl]hydrazono}butanoate (8), (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid N'-[(4-trifluoromethylphenylimino)methyl] hydrazide (9) and (7-hydroxy-2-oxo-2H-chromen-4-yl)acetic acid N'-[(2,3,4-trifluorophenylimino)-methyl] hydrazide (10). Cyclo-condensation of compound 2 with pentane-2,4-dione gave 4-[2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-oxoethyl]-7-hydroxy-2H-chromen-2-one (11), while with carbon disulfide it afforded 7-hydroxy-4-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-2H-chromen-2-one (12) and with potassium isothiocyanate it gave 7-hydroxy-4-[(5-mercapto-4H-1,2,4-triazol-3-yl)methyl]-2H-chromen-2-one (14). Compound 7 was cyclized to afford 2-(7-hydroxy-2-oxo-2H-chromen-4-yl)-N´-(4-oxo-2-phenyliminothiazolidin-3-yl) acetamide (15). Molecules 2006, 11 135

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Some Derivatives on the Basis (7-hydroxy-2-oxo-2H-chromen-4-yl)-acetic Acid Hydrazide

Trkovnik²,

et al. 2006

Molecules

CHEMICAL & PHARMACEUTICAL BULLETIN

“…The number of natural and synthetic coumarin (2H-chromen-2-one) derivatives 1) have been reported to exert notably antimicrobial 2,3) as well as antifungal, 4,5) tuberculostatic 6) and anti-human immunodeficiency virus (HIV) 7,8) activity. Moreover, the antibiotic novobiocin belongs to the hydroxycoumarin series.…”

mentioning

confidence: 99%

Electrochemical Synthesis of 4-(Dihydroxyphenylthio)-2H-chromen-2-one Derivatives

Nematollahi

Azizian

Sargordan-Arani

et al. 2008

The number of natural and synthetic coumarin (2H-chromen-2-one) derivatives 1) have been reported to exert notably antimicrobial 2,3) as well as antifungal, 4,5) tuberculostatic 6) and anti-human immunodeficiency virus (HIV) 7,8) activity. Moreover, the antibiotic novobiocin belongs to the hydroxycoumarin series. The importance of these compounds have motivated many workers to synthesize a number of them, and numerous methods have been developed for their preparation.9-11) On the other hand, catechols are a promising group of compounds worthwhile for further investigation, which may lead to the discovery of selective acting, biodegradable agrochemicals having high human, animal and plant compatibility. 12,13) A literature survey reveals that, in contrast to the widely studied, coumarin derivatives, no paper has reported the synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives. Following our experiences in electrochemical oxidation of catechols in the presence of nucleophiles, [14][15][16][17][18][19][20][21] we envisaged that synthesis of organic compounds with both structures of catechol and coumarin might cause an enhancement of pharmaceutical properties and medicinal activities. This idea prompted us to investigate the electrochemical oxidation of catechols in the presence of 4-mercaptocoumarin as the nucleophile and we have discovered an easy and one-pot electrochemical method for the synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives (4a-d) in high yield and purity, using this environmentally friendly method with high atom economy. In order to study the feasibility of the electrochemical synthesis of 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives (4a-d) and mechanistic aspects of this conversions, electrochemical oxidation of catechols in the absence and presence of 4-mercaptocoumarin was studied using cyclic voltammetry. As well, in this work computational studies were used for quantitative answer to the question concerning the difference in electrochemical oxidation of catechol in the presence of 4-hydroxycoumarin and 4-mercaptocoumarin. Results and DiscussionElectrochemical Studies Figure 1, curve a, shows the voltammetric curve obtained for the oxidation of catechol (1 mM) in water/acetonitrile (50/50) solution containing sodium acetate (cϭ0.2 M) on a glassy carbon electrode. In the studied potential-range, a well defined voltammetric curve is obtained that has an anodic (A 1 ) and the corresponding cathodic (C 1 ) peaks. These peaks are correspond to the oxidation of catechol (1a) to o-benzoquinone (2a) and vice versa within a quasi-reversible two electron process.14-21) The oxidation of catechol (1a) in the presence of 4-mercaptocoumarin (3) as a nucleophile was studied in some details. The 4-(dihydroxyphenylthio)-2H-chromen-2-one derivatives have been synthesized by direct electrochemical oxidation of catechols in the presence of 4-mercaptocoumarin as a nucleophile in water/acetonitrile (50/50) solution, in a one-pot process, at carbon rod electrode, in an undivided...

“…Benzopyranes constitute an important class of compounds that occurs frequently in medical plants extracts (Calophyllum) (Gabor, 1988). Coumarin (1,2-benzopyrone) is the complex member of a benzopyranes (Abd-Allah, 2000). Coumarin derivatives are naturally occurring substances with multiple biological activities, due to their extensive occurrence in nature and low toxicity with a very short biological half-life, where they rapidly eliminated via urine (Maxwell, 1993;Fernandez et al, 1996;Nofal et al, 2000;Giota et al, 2001;Kostova, 2005).…”

Section: Introductionmentioning

confidence: 99%

Novel inhibition of some pathogenic fungal and bacterial species by new synthetic phytochemical coumarin derivatives

Geweely

2009

Ann. Microbiol.