Syntheses and Biological Activities of Chroman-2-ones. A Review

Kamat, Durga P.; Tilve, Santosh G.; Kamat, Vijayendra P.; Kirtany, J. K.

doi:10.1080/00304948.2015.983805

Cited by 50 publications

(23 citation statements)

References 267 publications

(184 reference statements)

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“…Chromanones and their related heterocyclic ring system (Scheme 2, top to the left) are widely distributed in natural products and biologically active molecules [39,40,41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56,57,58]. Similarly, compounds with an incorporated α,α-disubstituted amino acid moiety exhibit diverse biological activity [59,60,61,62,63,64].…”

Section: Resultsmentioning

confidence: 99%

Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction

2019

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In this manuscript, a novel, decarboxylative Michael reaction between α-substituted azlactones and chromone-3-carboxylic acids is described. The reaction proceeds in a sequence Michael addition followed by decarboxylative deprotonation, and it results in the formation of chromanones bearing an azlactone structural unit. The possibility of transforming an azlactone moiety into a protected α,α-disubstituted α-amino acid derivative is also demonstrated.

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Section: Resultsmentioning

confidence: 99%

Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction

2019

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“…The pyridine and chromanone motifs are found in various natural products ( Scheme 1 ). The chromanone ring system (chroman-2-on and chroman-4-on) and related compounds are found in different bioactive molecules relevant for the life-science industry [ 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 ]. Although these compounds are abundant in nature, synthetic methods for their preparation are not very common.…”

Section: Introductionmentioning

confidence: 99%

Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions

Bojanowski

Albrecht

2021

Molecules

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The doubly decarboxylative Michael–type addition of pyridylacetic acid to chromone-3-carboxylic acids or coumarin-3-carboxylic acids has been developed. This protocol has been realized under Brønsted base catalysis, providing biologically interesting 4-(pyridylmethyl)chroman-2-ones and 2-(pyridylmethyl)chroman-4-ones in good or very good yields. The decarboxylative reaction pathway has been confirmed by mechanistic studies. Moreover, attempts to develop an enantioselective variant of the cascade are also described.

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“…Among various biological activities, they often display strong anticancer activity . Although less common in nature, chroman‐2‐ones 2 or 3,4‐dihydrocoumarins also show various biological activities, and their cytotoxic activity is well recognized . For example, coumarin glycosides 3 isolated from the aerial parts of Diceratella elliptica show high activity against three human carcinoma cell lines: liver (HepG2), cervical (HeLa) and colon (HCT116).…”

Section: Introductionmentioning

confidence: 99%

“…[2,3] Althoughl ess common in nature, chroman-2-ones 2 or 3,4-dihydrocoumarins also show various biological activities, and their cytotoxic activity is well recognized. [4] For example, coumarin glycosides 3 isolated from the aerial parts of Diceratella elliptica show high activity against three human carcinoma cell lines: liver (HepG2), cervical (HeLa) and colon (HCT116). Also, variously substitutedd ihydrocoumarin derivatives 4 were found to be sirtuin inhibitors (SIRTi-silent information regulator inhibitors), and have showna ntiproliferative properties and tubulin hyper-acetylation in MCF-7b reast cancerc ells [5] as well as high proapoptotic and cell-differentiating properties in human leukemia cell line (U937).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 4,4‐Disubstituted 3‐Methylidenechroman‐2‐ones as Potent Anticancer Agents

et al. 2017

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The synthesis of a new library of 4,4-disubstituted 3-methylidene-3,4-dihydro-2H-chroman-2-ones applying Horner-Wadsworth-Emmons methodology for the construction of an exo-methylidene moiety is reported. Corresponding 3-diethoxyphosphorylchroman-2-ones were synthesized in a three-step reaction sequence consisting of O-methylation of ethyl 2-diethoxyphosphoryl-3-oxoalkanoates, followed by reaction of the obtained 2-diethoxyphosphoryl-3-methoxy-2-alkenoates with phenols or 1-naphthol. The resulting 3-diethoxyphosphorylochromen-2-ones proved to be effective Michael acceptors in reactions with various Grignard reagents. Preliminary biological evaluations showed that many of the synthesized 3-methylidenechroman-2-ones possess very high cytotoxic activity against NALM-6 and HL-60 cancer cell lines (IC <1.0 μm) as well as high activity against the MCF-7 cancer cell line (IC <10 μm). Furthermore, two of the highly active 3-methylidenechroman-2-ones with geminal methyl and ethyl substituents at position 4 showed promising therapeutic indexes of 10 and 13 in tests against human umbilical vein endothelial cells (HUVECs).

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Syntheses and Biological Activities of Chroman-2-ones. A Review

Cited by 50 publications

References 267 publications

Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction

Enantioselective Synthesis of Chromanones Bearing an α,α-Disubstituted α-Amino Acid Moiety via Decarboxylative Michael Reaction

Doubly Decarboxylative Synthesis of 4-(Pyridylmethyl)chroman-2-ones and 2-(Pyridylmethyl)chroman-4-ones under Mild Reaction Conditions

Synthesis of 4,4‐Disubstituted 3‐Methylidenechroman‐2‐ones as Potent Anticancer Agents

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