Synthesis and antitubercular activity evaluation of 4-furano-coumarins and 3-furano-chromones

Singh, Ankita; Bimal, Devla; Kumar, Rajesh; Maikhuri, Vipin K.; Thirumal, M.; Senapati, Nihar Nalini; Prasad, Ashok K.

doi:10.1080/00397911.2018.1480041

Cited by 23 publications

(5 citation statements)

References 42 publications

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“…The authors believe that the cell wall lipoproteins of M. tuberculosis are the major target for these compounds. 20 (Chromon-3-yl)triazolylmethane derivative 6 showed antimycobacterial activity similar to that of Rifampicin. 21 The most known methods for the synthesis of isofl avone heterocyclic analogs involve preliminary synthesis hetaryl desoxybenzoins and their subsequent cyclization.…”

Section: Introductionmentioning

confidence: 90%

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

et al. 2021

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The review is focused on recent developments of chemistry of synthetic analogs of natural compounds, isofl avone and homoisofl avone. The possible synthetic strategies to access heterocyclic analogs of these compounds starting from readily available 3-formylchromone and its derivatives (3-cyanochromone, 2-amino-3-formylchromone) and products of its condensation with simplest Cand N-nucleophiles are discussed. The structural features of the reaction products that depend on the nature of the reaction medium, structure of the starting compounds, and reagent ratio are considered. Particular attention is given to the application of the modern strategies of organic synthesis, namely green chemistry approaches, click reactions, domino reactions, etc. Examples of compounds of this group most promising for clinical application due to wide and pronounced pharmacological eff ects are given.

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Section: Introductionmentioning

confidence: 90%

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

et al. 2021

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“…Firstly, the intermediate was synthesized through the condensation of o -hydroxy acetophenone with DMF. Then it was cyclized under the action of iodine to generate 3-iodochromone [ 199 ]. Isoflavones were finally obtained by the cross-coupling of 3-iodochromones with arylboronic acids [ 200 ].…”

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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“…A common approach to obtain a wide variety of 3-substituted 4H-chromen-4-ones is using (E)-3-(dimethylamino)-1-(2-hydroxyaryl) prop-2-en-1-ones, commonly known as o-hydroxyaryl enaminones, as key intermediates, obtained mainly from the reaction of 2 0 -hydroxyacetophenones with DMF-DMA in DMF as solvent. Various 3-iodo-4H-chromen-4-ones arise from one-pot ring-closure and iodination sequence via addition of molecular iodine to o-hydroxyaryl enaminones employing methanol, [242][243][244][245][246][247] chloroform, 248,249 pyridine and chloroform, [250][251][252][253][254] pyridine and dichloromethane 47,255 as solvents, at room temperature. Examples of 3-fluoro-4H-chromen-4-ones were synthesized through the monofluorination of o-hydroxyaryl enaminones with Selectfluor ® as fluorine source in 1,2-DCE at room temperature, 256 in the presence of sodium acetate and butylated hydroxytoluene (BHT)…”

Section: Via O-hydroxyaryl Enaminone Formationmentioning

confidence: 99%

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

Santos

Silva

2022

Advances in Heterocyclic Chemistry

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Synthesis and antitubercular activity evaluation of 4-furano-coumarins and 3-furano-chromones

Cited by 23 publications

References 42 publications

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

Synthesis of heterocyclic analogs of isoflavone and homoisoflavone based on 3-formylchromone

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

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

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