Synthesis and biological evaluation of flavonoids and related compounds as gastroprotective agents

Ares, Jeffrey J.; Outt, P. E.; Randall, J. L.; Johnston, Jeffrey N.; Murray, Peter D.; O’Brien, Linda; Weisshaar, P. S.; Ems, Beth L.

doi:10.1016/0960-894x(96)00134-5

Cited by 36 publications

(4 citation statements)

References 15 publications

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“…4±Benzopyrones (also known as chromen-4-ones or 4H-1benzopyran-4-ones) have attracted considerable attention because of their presence in numerous natural products and synthetic drugs (e.g. in amlexanox; Nohara et al, 1985) and their potential pharmacological activities, such as gastroprotective effect (Ares et al, 1996), in vivo iron-chelating activity (Ferrali et al, 2001), antioxidizing effect in aldose reductase inhibition (Costantino et al, 1999), acaricidal activity (Gleye et al, 2003), monoamine oxidase inhibition (Sloley et al, 2000), and anti-anaphylactic activity (Nohara et al, 1977). In addition, some benzopyrones, such as 3-cyano-4benzopyrone, are important intermediates in the synthesis of therapeutically useful anti-allergic and some anti-in¯ammatory drugs (Nohara et al, 1985;Reddy et al, 2004).…”

Section: Commentmentioning

confidence: 99%

2,6-Dimethyl-4H-1-benzopyran-4-one

2004

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The title compound, C11H10O2, belongs to the class of 4‐benzopyrones (also known as chromen‐4‐ones) with potentially diverse pharmacological activities. It was synthesized by acylation of 2‐hydroxy‐4‐methylacetophenone with ethyl acetate in the presence of sodium hydride and subsequent cyclization by hydrochloric acid. All non‐H atoms of the substituted bicyclic molecule are coplanar within 0.03 Å. C—H⋯O interactions [C⋯O = 3.272 (5) Å] link neighbouring molecules related by the 21 axis.

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Section: Commentmentioning

confidence: 99%

2,6-Dimethyl-4H-1-benzopyran-4-one

2004

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“…These are the main precursor in the biosynthesis of flavonoids [ 2 ] abundant in edible plants. They have been reported to show various pharmacological activities like anticancer [ 3 , 4 ], antimalarial [ 5 ], anti-inflammatory [ 6 ], anti-tubercular [ 7 ], cytotoxic [ 8 ], gastroprotective [ 9 ], modulation of nitric oxide production [ 10 ] and so on. These compounds are important synthons for the preparation of five and six membered ring systems [ 11 ] as well as intermediate in the synthesis of many pharmaceuticals [ 12 ].…”

Section: Introductionmentioning

confidence: 99%

Microwave assisted solvent free synthesis of 1,3-diphenylpropenones

Kakati

Sarma

2011

Chemistry Central Journal

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Background1,3-Diphenylpropenones (chalcones) are well known for their diverse array of bioactivities. Hydroxyl group substituted chalcones are the main precursor in the synthesis of flavonoids. Till date various methods have been developed for the synthesis of these very interesting molecules. Continuing our efforts for the development of simple, eco-friendly and cost-effective methodologies, we report here a solvent free condensation of aryl ketones and aldehydes using iodine impregnated alumina under microwave activation. This new protocol has been applied to a variety of substituted aryl carbonyls with excellent yield of substituted 1,3-diphenylpropenones.ResultsDifferently substituted chalcones were synthesized using iodine impregnated neutral alumina as catalyst in 79-95% yield in less than 2 minutes time under microwave activation without using any solvent. The reaction was studied under different catalytic conditions and it was found that molecular iodine supported over neutral alumina gives the best yield. The otherwise difficult single step condensation of hydroxy substituted aryl carbonyls is an attractive feature of this protocol to obtain polyhydroxychalcones in excellent yields. In order to find out the general applicability of this new endeavor it was successfully applied for the synthesis of 15 different chalcones including highly bioactive prenylated hydroxychalcone xanthohumol.ConclusionA new, simple and solvent free method was developed for the synthesis of substituted chalcones in environmentally benign way. The mild reaction conditions, easy work-up, clean reaction profiles render this approach as an interesting alternative to the existing methods.

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“…Some chalcone derivatives are used as sweeteners, drugs and sunscreen agents. 15 Various substituted chalcones have been reported to possess antibacterial 16 antiulcer, 17 antifungal, l8 antioxidant, 19 vasodilatory, 20 antimitotic, 21 antimalarial 22 and antileishmanial, 23 and leukotriene B4, 24 inhibitory activities.…”

Section: Introductionmentioning

confidence: 99%

Microwave assisted synthesis of 1H-tetrazole-based flavonoid derivatives and their antimicrobial activity

Ashok

Nagaraju

Sarasija

et al. 2018

JSCS

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A series of novel tetrazole scaffolds containing chalcones 4a-e and aurones 5a-e were synthesized under conventional and microwave irradiation conditions. All the newly synthesized compounds were characterized by IR, NMR and mass spectral data. Furthermore, the title compounds were screened in vitro for their antimicrobial activity against bacteria, such as Staphylococus aureus, Bacillus subtilis, Klebsiella pneumoniae and Escherichia coli, as well as fungi, such as Aspergillus niger, A. flavus and Fusarium oxysporum. Some of the compounds showed very good activity compared to standard drugs against all the tested pathogenic bacteria and fungi.

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Synthesis and biological evaluation of flavonoids and related compounds as gastroprotective agents

Cited by 36 publications

References 15 publications

2,6-Dimethyl-4H-1-benzopyran-4-one

2,6-Dimethyl-4H-1-benzopyran-4-one

Microwave assisted solvent free synthesis of 1,3-diphenylpropenones

Microwave assisted synthesis of 1H-tetrazole-based flavonoid derivatives and their antimicrobial activity

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