Synthesis of some new biologically-active coumarin derivatives

El-Sayed, A. M. A.; Ghattas, Abd-El-Badih A. G.; El‐Wassimy, M. T. M.; Allah, O. A. Abd

doi:10.1016/s0014-827x(98)00099-8

Cited by 21 publications

(5 citation statements)

References 2 publications

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“…They possess significant biological activities (1)(2)(3) , anti-bacterial (4) , anti-tumoral (5) , and anti-HIv (6)(7)(8)(9) . Due to those varied biological activities, we have synthesized several 4-substituted, 4,3-substituted-2H-1-benzopyran-2-one derivatives in order to investigate the structure activity relationships of coumarin derivatives.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 4-Hydroxy-3-Substituted Coumarins of Expected Biological Activity and Their Reactions With Some Nucleophiles

El-Ghaffar

Dawood

El-Salam

et al. 2008

Al-Azhar Bulletin of Science

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Abstract3-Acetyl-4-hydroxy substituted coumarins (II a-c ) were prepared. Their reactions with hydrazines in DMF gave the corresponding 4-hydroxy -(3-substituted pyrazolin-3-yl)coumarins (IV a-f ) via the intermediate hydrazone (III). Their reaction with hydroxylamine hydrochloride gave the corresponding isoxazol-3-yl coumarin (VI a-c ) and (VII a,b ) via the oxime intermediate (V). Reaction of II with aromatic aldehydes gave the corresponding chalcone derivatives (VIII a-k ) which were reacted with hydrazines and hydroxyl amine hydrochloride and gave (IX a ) and (X a-c ). Condensation of (II a-c ) with aromatic aldehydes, malononitrile in the presence ammonium acetate yielded the corresponding 3-cyano-4-aryl nictoinamido-6-ylcoumarin (XI a-f ). 4-Hydroxy comumarin(1 a-c ) on treatment with POCl 3 in DMF give the corresponding 4-Chloro-3-formyl coumarin (XII a-c ) which on treatment with sod azide gave the corresponding 4-azido-3-formyl coumarin (XIII a-c ). 4-chloro-3-formyl coumarine (XII )on treatment with hydrazine gave pyrazolo coumarin derivatives (XIV a-d ) and on treatment with hydroxylamine hydrochloride gave 4-chloro-3-aldo oxime coumarin derivatives (XV a,b ). On treatment of 4-azido-3-formyl coumarin with active methylene compounds such as malononitrile and ethyl cyanocetate derivatives gave (XVI a-d ) respectively.The antibacterial and antifungal activities of some compounds have been described.

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Section: Resultsmentioning

confidence: 99%

Synthesis of 4-Hydroxy-3-Substituted Coumarins of Expected Biological Activity and Their Reactions With Some Nucleophiles

El-Ghaffar

Dawood

El-Salam

et al. 2008

Al-Azhar Bulletin of Science

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“…Some benzopyranopyrazoles have been reported to act on the nervous system with anxiolytic, hypnotic, and anticonvulsant properties . In addition, this kind of compounds has been proposed as antihypertensive , antibacterial , diuretic, uricosuric, and vasodilative agents. They have also been studied as insecticides in agro‐alimental field and also as inhibitors of necroptosis .…”

Section: Introductionmentioning

confidence: 99%

A Simple Efficient Procedure for the Synthesis of Benzopyrano[2,3‐c]pyrazoles

Turki

Kamoun

Lahiani

et al. 2016

Journal of Heterocyclic Chem

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A one‐step procedure is proposed for synthesizing 2‐acyl benzopyrano[2,3‐c]pyrazoles and 2‐aryl benzopyrano[2,3‐c]pyrazoles. The method is based on the condensation of 2‐iminocoumarin‐3‐carbonitriles with hydrazides and hydrazines in acid as catalysts. A mechanism of reaction is proposed. All prepared compounds are identified by FTIR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis.

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“…Coumarins constitute an important class of naturally occurring compounds with useful pharmacological activity [1][2][3][4][5][6] as antibacterial [7][8][9][10][11][12] and antifungal agents. [13][14][15][16][17] The result of the variety of the physiological activity of pyrroloindole derivatives [18][19] and also the possibility of their use in the synthesis of alkaloids and alkaloid related substances.…”

mentioning

confidence: 99%

Synthesis and anti-bacterial screening of ethyl 6-oxo-3-phenyl-1,6-dihydropyrano[3,2-e]indole-2-carboxylate and 7-phenyl-5H-pyrano [3′,2′:4,5]indolo[1,2-a]quinoxaline-6,10-dione

Mir

Mulwad

2009

Journal of Chemical Research

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Ethyl 6-oxo-3-phenyl-1,6-dihydropyrano[3,2-e]indole-2-carboxylate 3a-c were synthesised from ethyl 2-[(2-oxo-2H-1-benzopyran-6-yl)-hydrazono]-3-phenylpropanoate 2a-c. Compounds 2a-c was in turn prepared by reacting diasotised solution of 6-aminocoumarin and ethyl-2-benzylacetoacetate. N-nitroarylation of ethyl 6-oxo-3-phenyl-1,6-dihydropyrano[3,2-e]indole-2-carboxylate 3a-c was carried out with 2-chloronitrobenzene to give ethyl 1-(2-nitrophenyl)-6-oxo-3-phenyl-1,6-dihydropyrano[3,2-e]indole-2-carboxylate 4a-c, which on catalytic reductive cyclisation with H 2 /Ni affords 7-phenyl-5H-pyrano[3',2':4,5]indolo[1,2-a]quinoxaline-6,10-dione 5a-c. The structures of all these compounds have been established on the basis of analytical and spectral data. All the compounds show significant antibacterial activity.

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Synthesis of some new biologically-active coumarin derivatives

Cited by 21 publications

References 2 publications

Synthesis of 4-Hydroxy-3-Substituted Coumarins of Expected Biological Activity and Their Reactions With Some Nucleophiles

Synthesis of 4-Hydroxy-3-Substituted Coumarins of Expected Biological Activity and Their Reactions With Some Nucleophiles

A Simple Efficient Procedure for the Synthesis of Benzopyrano[2,3‐c]pyrazoles

Synthesis and anti-bacterial screening of ethyl 6-oxo-3-phenyl-1,6-dihydropyrano[3,2-e]indole-2-carboxylate and 7-phenyl-5H-pyrano [3′,2′:4,5]indolo[1,2-a]quinoxaline-6,10-dione

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