Synthesis and biological activity of chromones annelated at the C(7)–C(8) bond with heterocycles (review)

Лозинский, О. А.; Shokol, T. V.; Khilya, V. P.

doi:10.1007/s10593-011-0876-z

Cited by 22 publications

(7 citation statements)

References 67 publications

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“…10 Hence, chromones can be considered privileged structures, defined as "a single molecular framework ableto provide ligands for diverse receptors". 11 Prompted by all these observations, we report herein the synthesis, in vitro antioxidant and antimicrobial activities of 3-hydroxy chromone derivatives.…”

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confidence: 99%

Synthesis, In Vitro Antioxidant and Antimicrobial Evaluation of 3-Hydroxy Chromone Derivatives

2018

IJCTR

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3-hydroxy chromones were synthesized by Algar Flynn Oyamada method which includes oxidative cyclization of 2-hydroxy chalcones in basic solution by hydrogen peroxide. Chalcones required were synthesized by Claisen-Schmidt condensation of substituted 2hydroxy acetophenones with substituted aromatic aldehydes using PEG-400 as recyclable solvent. The synthesized compounds were evaluated for in vitro antioxidant activity by 1,1diphenyl-2-pycrylhydrazyl radical scavenging assay. Additionally, these compounds were also screened for in vitro antibacterial and antifungal activity by agar cup method and Poison plate method, respectively. The structures of the synthesized compounds were characterized by IR, 1 H NMR and Mass spectra. The antioxidant activity data revealed that all the synthesized derivatives of chromone showed greater antioxidant activity due to presence of phenolic hydroxyl group, 4-oxo group and 2,3-double bond. Further the activity increased with introduction of more phenolic hydroxyl group and adjacent methoxy group in the structure. The antimicrobial activity data showed that the compounds exhibited good antibacterial and antifungal activity which is attributed to the presence of phenolic hydroxyl group and 4-oxo group in the structure.

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confidence: 99%

Synthesis, In Vitro Antioxidant and Antimicrobial Evaluation of 3-Hydroxy Chromone Derivatives

2018

IJCTR

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“…The latter compound was also obtained by either refluxing 83 with glacial acetic acid (Table 2) or by treating 50 with diethyl malonate in the presence of piperidine [39] (Scheme 19, Table 3). At the same time, it is surprising that, as previously described by the same authors, interaction of 6-formyl-7-hydroxy-5-methoxy-2-methylchromone (6) with ethyl cyanoacetate (53) in ethanol in the presence of piperidine while refluxing for 1 h led to the corresponding 3-cyano derivative 110 [36] (Table 2).…”

Section: Introductionmentioning

confidence: 71%

“…ortho-Hydroxyformyl(acetyl)chromones are treated as attractive starting materials for the synthesis of angular and linear hetarenochromones by the first route. The syntheses of angular hetarenochromones have been highlited in reviews [6,7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of linear hetarenochromones based on 7-hydroxy-6-formyl(acetyl)chromones

2021

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Fused chromones are attracting increasing attention as novel therapeutic agents due to their wide distribution in nature, effective bioactivities and low toxicity. 6-Carbonyl-7-hydroxychromones proved to be versatile synthons for the synthesis of linear hetarenochromones by annulation of heterocycle to the chromone core. The present review is focused on the syntheses of furo[3,2-g]chromones, pyrano[3,2-g]chromones and some of their N-containing analogues, namely chromeno[6,7-d]isoxazoles, pyrano[3’,2’:6,7]chromeno[4,3-b]pyridine-5,11-diones and pyrano[3’,2’:6,7]chromeno[4,3-c]pyridine-5,11-diones based on the 7-hydroxy-6-formylchromones or 7-hydroxy-6-acetylchromones and shows the current state of research to date. The methods for the synthesis of the starting 7-hydroxy-6-formylchromones and 7-hydroxy-6-acetylchromones have been also mentioned. The biological activity of naturally occurring and modified synthetic linear hetarenochromones has been also represented.

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“…Known effects of these types of compounds are antioxidant [5], antiviral [6], antibacterial [7], antifungal, antiinflammatory [8], antiobesity [9], immunomodulatoty [10], and kinase inhibition [11]. Hence, chromones can be considered privileged structures, defined as "a single molecular framework able to provide ligands for diverse receptors" [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, in Vitro Antioxidant and Antimicrobial Evaluation of 3-Hydroxy Chromone Derivatives

Kamble

Wadher

2018

Asian J Pharm Clin Res

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Objective: The objective of the present study was to synthesize a series of 3-hydroxychromone derivatives and to evaluate its in vitro antioxidant and antimicrobial activities.Methods: 3-hydroxy chromones were synthesized using an algar flynn oyamada method which includes oxidative cyclization of 2-hydroxy chalcones in basic solution by hydrogen peroxide. 2-hydroxy chalcones were synthesized by Claisen-Schmidt condensation of substituted 2-hydroxy acetophenones with substituted aromatic aldehydes using polyethylene glycol-400 as a recyclable solvent. The synthesized compounds were evaluated for in vitro antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay. In addition, these compounds were also screened for in vitro antibacterial and antifungal activity by agar cup method and Poison plate method, respectively.Results: The structures of the synthesized compounds were characterized by infrared, 1H nuclear magnetic resonance and mass spectroscopy. The antioxidant activity data revealed that all the synthesized derivatives exhibited good activity due to the presence of phenolic hydroxyl group, 4-oxo group and 2,3-double bond. Further, the activity increased with the introduction of a more phenolic hydroxyl group and adjacent methoxy group in the structure. The antimicrobial activity data showed that the compounds possess better antibacterial and antifungal activity which is attributed to the presence of phenolic hydroxyl group and 4-oxo group in the structure.Conclusions: The use of inexpensive, eco-friendly and readily available reagents, easy work-up and high purity of products makes the procedure a convenient and robust method for the synthesis of title compounds. The presence of phenolic hydroxyl group, 4-oxo group, and 2,3-double bond in the structure is responsible for their good antioxidant and antimicrobial activities.

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Synthesis and biological activity of chromones annelated at the C(7)–C(8) bond with heterocycles (review)

Cited by 22 publications

References 67 publications

Synthesis, In Vitro Antioxidant and Antimicrobial Evaluation of 3-Hydroxy Chromone Derivatives

Synthesis, In Vitro Antioxidant and Antimicrobial Evaluation of 3-Hydroxy Chromone Derivatives

Synthesis of linear hetarenochromones based on 7-hydroxy-6-formyl(acetyl)chromones

Synthesis, in Vitro Antioxidant and Antimicrobial Evaluation of 3-Hydroxy Chromone Derivatives

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