An efficient synthesis of flavanones and their docking studies with aldose reductase

Kondhare, Dasharath; Gyananath, G.; Tamboli, Yasinalli; Kumbhar, Santosh S.; Choudhari, Prafulla B.; Bhatia, Meenakshi; Zubaidha, P. K.

doi:10.1007/s00044-017-1813-1

Cited by 19 publications

(13 citation statements)

References 39 publications

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“…The presence of the lactone moiety was confirmed in the IR spectra by absorption bands corresponding to C=O and C-O bonds in the region of 1766 to 1773 cm −1 and 1205 to 1236 cm −1 , respectively. One can see a significant difference between the absorption of carbonyl moiety in these seven-membered rings in comparison with flavanones 4a – f , in which the carbonyl group absorbs in the region of 1670 to 1690 cm −1 [44]. On the 1 H-NMR spectra, the protons of the CH 2 -3 methylene group are non-equivalent (diastereotopic) due to the presence of a chiral center and they couple to each other and the adjacent methine C-4 proton.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

et al. 2019

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Six γ-oxa-ε-lactones, 4-phenyl-3,4-dihydro-2H-1,5-benzodioxepin-2-one (5a) and its five derivatives with methoxy groups in different positions of A and B rings (5b–f), were synthesized from corresponding flavanones. Three of the obtained lactones (5b,c,f) have not been previously described in the literature. Structures of all synthesized compounds were confirmed by complete spectroscopic analysis with the assignments of signals on 1H and 13C-NMR spectra to the corresponding atoms. In most cases, lactones 5a–f exerted an inhibitory effect on the growth of selected pathogenic bacteria (Escherichia coli, Bacillus subtilis, and Staphylococcus aureus), filamentous fungi (Fusarium graminearum, Aspergillus niger, and Alternaria sp.), and yeast (Candida albicans). The broadest spectrum of activity was observed for unsubstituted lactone 5a, which was particularly active against filamentous fungi and yeast. Lactones with methoxy groups in the 3′ (5c) and 4′ (5d) position of B ring were more active towards bacteria whereas lactone substituted in the 7 position of the A ring (5e) exhibited higher antifungal activity. In most cases, the introduction of lactone function increased the activity of the compound compared to its flavonoid precursors, chalcones 3a–e, and flavanones 4a–f.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

et al. 2019

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“…Under dual catalysis of FeCl 3 and piperidine, flavones could also be directly supplied from salicylaldehyde derivatives and substituted phenylacetylenes with atmospheric oxygen as the stoichiometric oxidant [ 186 ] (Scheme 18 c). As the reduction state of flavones, flavanones could be directly synthesized from 2-hydroxyacetophenone and benzaldehyde by the catalysis of aniline via Mannich-type reaction [ 187 , 188 ] (Scheme 18 d). In addition to the cyclization of 2'-hydroxychalcones which is presented in Scheme 17 , aurone and its derivatives can be easily synthesized by Claisen-Schmidt reaction of aromatic aldehyde with benzofuranone derivative [ 189 ] (Scheme 18 e).…”

Section: Structural Derivatization Strategies Of Natural Phenols By T...mentioning

confidence: 99%

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

Ding

Jiang

Zhang

et al. 2022

Nat. Prod. Bioprospect.

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Structural derivatization of natural products has been a continuing and irreplaceable source of novel drug leads. Natural phenols are a broad category of natural products with wide pharmacological activity and have offered plenty of clinical drugs. However, the structural complexity and wide variety of natural phenols leads to the difficulty of structural derivatization. Skeleton analysis indicated most types of natural phenols can be structured by the combination and extension of three common fragments containing phenol, phenylpropanoid and benzoyl. Based on these fragments, the derivatization strategies of natural phenols were unified and comprehensively analyzed in this review. In addition to classical methods, advanced strategies with high selectivity, efficiency and practicality were emphasized. Total synthesis strategies of typical fragments such as stilbenes, chalcones and flavonoids were also covered and analyzed as the supplementary for supporting the diversity-oriented derivatization of natural phenols.

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“…Recently, several one-pot procedures for the preparation of flavanones via aniline-mediated cyclization of 2-hydroxyacetophenones and benzaldehydes have been reported ( Scheme 1a ). 13 Despite significant advances, the addition of aniline and longer reaction time are required. Therefore, it is still desirable to develop new efficient catalytic systems.…”

Section: Introductionmentioning

confidence: 99%

Polyphosphoric acid-promoted one-pot synthesis and neuroprotective effects of flavanones against NMDA-induced injury in PC12 cells

Wang¹,

Yang

Yang³

et al. 2022

RSC Adv.

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An efficient synthesis of flavanones and their docking studies with aldose reductase

Cited by 19 publications

References 39 publications

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones

Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis

Polyphosphoric acid-promoted one-pot synthesis and neuroprotective effects of flavanones against NMDA-induced injury in PC12 cells

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