2,2′,4‐Trihydroxybenzophenone: Crystal Structure, and Anti‐Inflammatory and Antioxidant Activities

Martins, Felipe Terra; Ellena, Javier; Salloum, Rogério; Santos, Marcelo H. dos; Moreira, Maria Eliza de Castro; Schneedorf, José Maurício; Nagem, Tânus Jorge

doi:10.1002/cbdv.200790041

Cited by 23 publications

(28 citation statements)

References 23 publications

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“…The shortening of certain aromatic C-C distances is reported in a series of related benzophenones. 30,31 Nevertheless, the aromatic distances found in (a) are in agreement with the range required for aromatic bonds, just as all aromatical C-C-C angles (mean of 120(4)°) coincided with the reference corners for the aromatic ring. In the same way, the C-C single and double bonds at the prenyl fragments present concordant distances in relation to similar prenylated compounds (mean distances of 1.311(4) Å for C=C, 1.500(4) Å for C sp 3 -C sp 2 and 1.549(5) Å for C sp 3 -C sp 3 ).…”

Section: Resultssupporting

confidence: 66%

“…These features are consequence of entire electronic delocalization through the atoms O2-C10-C3-C4-O1 that in solution lead to distinct tautomeric forms. 1,2,30 However, in the (a) crystal structure the model considering the C10-OH2 tautomer gives the best fitted final refinement indexes. In this way, from a statistical point of view revelled by XRD analysis, this model must be taken in account in the moment of structural assignments by NMR spectroscopic techniques performed in solution.…”

Section: Resultsmentioning

confidence: 99%

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Natural polyprenylated benzophenones: keto-enol tautomerism and stereochemistry

Martins¹,

Cruz²,

Derogis³

et al. 2007

J. Braz. Chem. Soc.

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Section: Resultssupporting

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Natural polyprenylated benzophenones: keto-enol tautomerism and stereochemistry

Martins¹,

Cruz²,

Derogis³

et al. 2007

J. Braz. Chem. Soc.

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“…The 2,2',4-trihydroxybenzophenone was capable of inhibiting the inflammatory process, reducing the diameter of the edema by 47.0 ± 10% after 2 h, and 34.0 ± 6% after 3 h. The 2,2',4-trihydroxybenzophenone showed similar efficacy for inhibition of rat-paw-edema than indomethacin, which inhibited the edematogenic process by 43.0 ± 4%, 51.0 ± 7%, and 52.0 ± 5% after 2, 3 and 4 h, respectively. 36 As stated above, serine-proteases, such as elastase, play an important role in inflammatory processes. Thus, these enzymes are targeted to explore in the direction of research and development of more effective anti-inflammatory compounds that can be employed in the therapeutic.…”

Section: Introductionmentioning

confidence: 98%

“…28,29 Several studies have shown the efficacy of triazole as potent elastase inhibitors. 30 Our research group has been involved in investigating several synthetic [33][34][35][36][37] and natural 38 benzophenones. For instance, the anti-inflammatory potential of 2,2',4-trihydroxybenzophenone was assessed by means of the rat-paw-edema induced by carrageenan application assay.…”

Section: Introductionmentioning

confidence: 99%

“…The 1,2,3-triazole functionality has gained tremendous interest of numerous researchers, since compounds containing this structural motif exhibits several biological activities, such as antituberculosis, 18 anticancer, Our research group has been involved in investigating several synthetic [33][34][35][36][37] and natural 38 benzophenones. For instance, the anti-inflammatory potential of 2,2',4-trihydroxybenzophenone was assessed by means of the rat-paw-edema induced by carrageenan application assay.…”

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Synthesis of 1,2,3-Triazole Derivatives of 4,4’-Dihydroxybenzophenone and Evaluation of Their Elastase Inhibitory Activity

Dias

Gularte

Teixeira

et al. 2018

J. Braz. Chem. Soc.

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The present investigation describes the synthesis of a series of novel triazole derivatives from 4,4'-dihydroxybenzophenone along with their elastase inhibitory activity. The 1,2,3-triazoles were obtained via the copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC), also known as click reaction, between bis(4-(prop-2-yn-1-yloxy))benzophenone and several benzyl azides. It was found that five derivatives exhibited significant inhibitory effects, presenting half maximal inhibitory concentration (IC 50 ) values in the range of 16.6 to 72.1 µM. The most active compound, namely bis(4-(1-(4-iodobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)benzophenone (IC 50 = 16.6 ± 1.9 µM), was found to bind to elastase with the inhibition constant (K i ) of 11.12 µM, thereby illustrating competitive inhibitory behavior. Further, docking investigations provided insights on the possible binding mode of the most active compound with the elastase.Keywords: elastase, serine protease, CuAAC reaction, benzophenone, 1,2,3-triazole IntroductionBenzophenones are of chemical, medicinal, and industrial interest.1 Several of their derivatives exhibit important biological activities like anticancer, 2,3 antiviral on HIV, 4 antibacterial, 5 activity against Alzheimer's disease, 6 and anti-inflammatory. 7The anti-inflammatory action of benzophenones is well documented in the literature. 8 For instance, ketoprofen is an example of synthetic benzophenone that has been commercialized as an anti-inflammatory drug. Recently, studies have demonstrated that structural modifications carried out on this drug afforded substances with improved anti-inflammatory activity. 9 Miyano et al. 10 synthesized a series of 4-(acyloxy)benzophenones and 4,4'-bis(acyloxy) benzophenones and evaluated their anti-inflammatory activity using human neutrophil elastase (HNE) as a template. The derivatives 4-(pivaloyloxy)benzophenone and 4-(isobutyryloxy)benzophenone showed elastase inhibitory activity with half maximal inhibitory concentration (IC 50 ) of 0.62 and 0.25 µM, respectively. It was found that 4,4'-bis(acyloxy)benzophenones were more potent than the corresponding 4-(acyloxy)benzophenones, highlighting 4,4'-bis(2,2-dimethylpropanoate)benzophenone with IC 50 = 0.12 µM and inhibition constant (K i ) = 7.1 × 10 -8 M.10 Serine proteases are involved in different branches of the immune system and play an important role in inflammation. In a recent investigation from our research group, Martins et al. 11 reported in vitro inhibition of serine proteases by synthetic and natural benzophenones, which showed moderate to high inhibitory effects against all the enzymes. Guttiferone A displayed IC 50 of 2.7 ± 0.1 µM, a value similar to the IC 50 of chymostatin (2.1 ± 0.1 µM), a classical inhibitor of serine protease cathepsin G. Braz. Chem. Soc. 98 Molecular hybridization has been shown to be a promising strategy for obtaining new compounds. It is mainly based on the combination of two or more known bioactive pharmacophoric fragments, by appropriate fusion, into a sing...

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Crystal Structure of Garciniaphenone and Evidences on the Relationship between Keto–Enol Tautomerism and Configuration

Martins

Camps

Santos

et al. 2008

Helvetica Chimica Acta

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Garciniaphenone (=rel‐(1R,5R,7R)‐3‐benzoyl‐4‐hydroxy‐8,8‐dimethyl‐1,7‐bis(3‐methylbut‐2‐en‐1‐yl)bicyclo[3.3.1]non‐3‐ene‐2,9‐dione; 1), a novel natural product, was isolated from a hexane extract of Garcinia brasiliensis fruits. The crystal structure of 1 as well as the selected geometrical and configurational features were compared with those of known related polyprenylated benzophenones. Garciniaphenone is the first representative of polyprenylated benzophenones without a prenyl substituent at C(5). Notably, the absence of a 5‐prenyl substituent has an impact on the molecular geometry. The tautomeric form of 1 in the solid state was readily established by a residual‐electronic‐density map generated by means of a difference Fourier analysis, and there is an entirely delocalized six‐membered chelate ring encompassing the keto–enol moiety. The configuration at C(7) was used to rationalize the nature of the keto–enol tautomeric form within 1. The intermolecular array in the network is maintained by nonclassical intermolecular H‐bonds.

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2,2′,4‐Trihydroxybenzophenone: Crystal Structure, and Anti‐Inflammatory and Antioxidant Activities

Cited by 23 publications

References 23 publications

Natural polyprenylated benzophenones: keto-enol tautomerism and stereochemistry

Natural polyprenylated benzophenones: keto-enol tautomerism and stereochemistry

Synthesis of 1,2,3-Triazole Derivatives of 4,4’-Dihydroxybenzophenone and Evaluation of Their Elastase Inhibitory Activity

Crystal Structure of Garciniaphenone and Evidences on the Relationship between Keto–Enol Tautomerism and Configuration

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