Synthesis and activity of a new series of chalcones as aldose reductase inhibitors

Severi, Fabio; Benvenuti, Stefania; Costantino, Luca; Vampa, G; Melegari, Margherita; Antolini, Luciano

doi:10.1016/s0223-5234(99)80010-5

Cited by 58 publications

(32 citation statements)

References 17 publications

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“…Most of the aldose reductase inhibitors from natural sources belong to phenolic compounds [10]. The structure studies for the inhibition of aldose reductase by phenolic compounds indicated that the acidity constants of hydroxylated compounds play an important role [11], and ortho-dihydroxyl phenolic compounds show marked inhibitory activities [12]. Therefore, we assumed that the inhibitory mode of curcuminoids and curcumin analogs was similar to that of flavones and chalcones.…”

Section: Resultsmentioning

confidence: 96%

Curcumin Analogs as Potent Aldose Reductase Inhibitors

Bao

Zhong

et al. 2006

Archiv der Pharmazie

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In the present study, curcuminoids isolated from curcuma longa were demonstrated to possess inhibitory activities on bovine lens aldose reductase. In order to find more potent aldose reductase inhibitor, curcumin analogs were synthesized and evaluated for their ability to inhibit bovine lens aldose reductase enzyme. The results indicated that the compounds with tetrahydroxyl groups, 2,6-bis(3,4-dihydroxybenzylidene)cyclohexanone (A(2)), 2,5-bis(3,4-dihydroxybenzylidene)cyclopentanone (B(2)), 1,5-bis(3,4-dihydroxyphenyl)-1,4-pentadiene-3-one (C(2)), and 3,5-bis(3,4-dihydroxybenzylidene)-4-piperidone (D(2)) showed remarkably potent inhibitory effects on aldose reductase with IC(50) of 2.9 microM, 2.6 microM, 3.4 microM, and 4.9 microM, respectively. The structure-activity relationship revealed that the curcumin analogs with ortho-dihydroxyl groups could form a more tight affinity with aldose reductase to exert more potential inhibitory activities.

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Section: Resultsmentioning

confidence: 96%

Curcumin Analogs as Potent Aldose Reductase Inhibitors

Bao

Zhong

et al. 2006

Archiv der Pharmazie

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“…[19] It also shows activity in vitro as an aldose reductase inhibitor. [20] In addition, it has been used as a nonlinear optical material [21] and as a molluscicide. [22] Subsequently, we extended the study of our Heck reaction to differently substituted aryl iodides.…”

Section: Resultsmentioning

confidence: 99%

The Heck Coupling Reaction Using Aryl Vinyl Ketones: Synthesis of Flavonoids

2004

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“…These studies show that chalcones are effective antihyperglycemic or hypoglycemic agents as much in vitro as in vivo experimental models [8,9,14]. It has been reported that sulfonamide chalcones act as a potent new class of a-glucosidase inhibitors [10,15].…”

Section: Introductionmentioning

confidence: 87%