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

Čačić, Milan; Trkovnik, M.; Čačić, Frane; Has-Schon, Elizabeth

doi:10.3390/11010134

Cited by 92 publications

(43 citation statements)

References 22 publications

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“…The existence of a methyl or methoxy group at the C-3 position of 1b and 1c causes the o-benzoquinones derived from the oxidation of these catechols (2b, 2c) attacked by 3 from C-4 or C-5 positions to yield two types of product in each case which has been confirmed by 1 H-NMR results. So, we suggest that o-benzoquinones 2b and 2c are attacked from two positions by 3 leading to the formation of the two types of product in each case (isomers A and B) (Chart 4).…”

Section: Chartsupporting

confidence: 59%

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

Nematollahi

Azizian

Sargordan-Arani

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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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...

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Section: Chartsupporting

confidence: 59%

“…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

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Coumarin is an important scaffold since several coumarin derivatives are known to be associated with multiple biological activities [8][9][10][11][12] and especially antiinflammatory/antioxidant activities. Recently the synthesis and in vivo/in vitro anti-inflammatory/antioxidant activities of several new coumarin derivatives with a 7-azomethine linkage have been reported [13].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents

Khode

Maddi

Aragade

et al. 2009

European Journal of Medicinal Chemistry

159

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“…The chemistry of thiosemicarbazones has received considerable attention because of their variable bonding modes, promising biological implications, structural diversity, and ion-sensing ability [20,21,22]. Thiazolidinones substituted in the 2-position, its derivatives and analogues exhibit unusually high in vitro activity against Mycobacterium tuberculosis [23,24,25]. In the current study we aimed to synthesize some new coumarins derived from umbelliferone (7-hydroxycoumarin) and thiazoles, with predictable biological activities.…”

Section: Introductionmentioning

confidence: 99%

The Use of Umbelliferone in the Synthesis of New Heterocyclic Compounds

et al. 2011

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New coumarin derivatives, namely 7-[(5-amino-1,3,4-thiadiazol-2-yl)methoxy]-2H-chromen-2-one (4), 5-[(2-oxo-2H-chromen-7-yloxy)methyl]-1,3,4-thiadiazol-2(3H)-one (5), 2-[2-(2-oxo-2H-chromen-7-yloxy)acetyl]-N-phenylhydrazinecarbothioamide (7), 7-[(5-(phenylamino)-1,3,4-thiadiazol-2-yl)methoxy]-2H-chromen-2-one (8) and 7-[(5-mercapto-4-phenyl-4H-1,2,4-triazol-3-yl)methoxy]-2H-chromen-2-one (9) were prepared starting from the natural compound umbelliferone (1). The newly synthesized compounds were characterized by elemental analysis and spectral studies (IR, 1H-NMR and 13C-NMR).

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

Cited by 92 publications

References 22 publications

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

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

Synthesis and pharmacological evaluation of a novel series of 5-(substituted)aryl-3-(3-coumarinyl)-1-phenyl-2-pyrazolines as novel anti-inflammatory and analgesic agents

The Use of Umbelliferone in the Synthesis of New Heterocyclic Compounds

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