Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases

Riafrecha, Leonardo E.; Rodríguez, Oscar Mariano; Vullo, Daniela; Supuran, Claudiu T.; Colinas, Pedro A.

doi:10.1016/j.bmc.2012.09.002

Cited by 30 publications

(20 citation statements)

References 35 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In this concept, a series of synthetic C-cinnamoyl glycosides were synthetized and considered for the inhibition on twelve mammalian isoforms of carbonic anhydrase (Figure 8) [52]. These compounds combined two functional groups with known activity against the hCAs: the cinnamoyl and the glucose group.…”

Section: Compoundmentioning

confidence: 99%

Phenols and Polyphenols as Carbonic Anhydrase Inhibitors

2016

View full text Add to dashboard Cite

Phenols are among the largest and most widely distributed groups of secondary metabolites within the plant kingdom. They are implicated in multiple and essential physiological functions. In humans they play an important role as microconstituents of the daily diet, their consumption being considered healthy. The physical and chemical properties of phenolic compounds make these molecules versatile ligands, capable of interacting with a wide range of targets, such as the Carbonic Anhydrases (CAs, EC 4.2.1.1). CAs reversibly catalyze the fundamental reaction of CO 2 hydration to bicarbonate and protons in all living organisms, being actively involved in the regulation of a plethora of patho/physiological processes. This review will discuss the most recent advances in the search of naturally occurring phenols and their synthetic derivatives that inhibit the CAs and their mechanisms of action at molecular level. Plant extracts or mixtures are not considered in the present review.

show abstract

Section: Compoundmentioning

confidence: 99%

Phenols and Polyphenols as Carbonic Anhydrase Inhibitors

2016

View full text Add to dashboard Cite

show abstract

“…A set of C-cinnamoyl glycosides (Figure 1) was synthesized as outlined in Scheme 1 and described previously by us 11 . C-cinnamoyl glycosides 1-4 have been prepared by aldol condensation of b-C-glucosyl and b-C-galactosyl ketones with 3-hydroxy or 4-hydroxybenzaldehyde at room temperature in the presence of pyrrolidine as catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…C-glycosides 1-8 were previously described and have been prepared by aldol reaction of aryl aldehydes with per-O-acetylated C-glucosyl or C-galactosyl ketones and subsequent deprotection using triethylamine in methanol/water 11 . An Applied Photophysics (Surrey, UK) stopped-flow instrument has been used for assaying the CA-catalyzed CO 2 hydration activity 15 .…”

Section: Methodsmentioning

confidence: 99%

“…Recently. our group has applied the ''sugar approach'' to the preparation of inhibitors of the M. tuberculosis b-CAs, which leads to the identification of the first mtCAs inhibitor with antimycobacterial activity 11,12 . Exploring alternative chemotypes to the usual CAIs, we developed a novel series of C-glycosides containing the methoxyaryl scaffold and investigated them as inhibitors against human and bacterial isozymes of carbonic anhydrase, allowing us to identify six potent and highly selective inhibitors of bsCA I and II 13,14 .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Inhibition ofβ-carbonic anhydrases fromBrucella suiswithC-cinnamoyl glycosides incorporating the phenol moiety

Riafrecha

Vullo

Ouahrani‐Bettache

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

A small series of C-glycosides containing the phenol moiety was tested for the inhibition of the b-class carbonic anhydrases (bCAs, EC 4.2.1.1) from Brucella suis. Many compounds showed activities in the micromolar or submicromolar range and excellent selectivity for pathogen CAs over human isozymes. Glycosides incorporating the 3-hydroxyphenyl moiety showed the best inhibition profile, and therefore this functionality represents lead for the development of novel anti-infectives with a new mechanism of action.

show abstract

“…The use of glycomimetics in the design of carbonic anhydrase inhibitors (CAIs) has proven to be a successful approach and now constitutes one of the most attractive ways to develop new generations of effective and selective inhibitors 8,10 . Recently one of our groups has applied the ''sugar approach'' to the preparation of C-cinnamoyl phenols, where the carbohydrate moiety is tethered to a phenol CA pharmacophore through a carbon chain 11 . These compounds have been tested as inhibitors of the Mycobacterium tuberculosis b-CAs and have shown better inhibitory activity against mtCAs than phenol.…”

Section: Introductionmentioning

confidence: 99%

Anti-tubercular and antioxidant activities of C-glycosyl carbonic anhydrase inhibitors: towards the development of novel chemotherapeutic agents against Mycobacterium tuberculosis

Zaro

Bortolotti

Riafrecha

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

Self Cite

View full text Add to dashboard Cite

During the treatment of tuberculosis infection, oxidative stress due to anti-tubercular drugs may result in tissue inflammation. It was suggested that treatment with antioxidant drugs could be beneficial as an adjunct to anti-tuberculosis drug therapy. Recently our group has shown that several C-glycosides are inhibitors of Mycobacterium tuberculosis b-carbonic anhydrases (CAs, EC 4.2.1.1). In an effort to develop novel chemotherapeutic agents against tuberculosis, the anti-tubercular and antioxidant activities of a series of C-glycosides containing the phenol or the methoxyaryl moiety were studied. Many compounds showed inhibition of growth of M. tuberculosis H 37 Rv strain and good antioxidant ability. A glycomimetic incorporating the 3-hydroxyphenyl moiety showed the best activity profile and therefore this functionality represents lead for the development of novel anti-tubercular agents with dual mechanisms of action.

show abstract

Synthesis of C-cinnamoyl glycosides and their inhibitory activity against mammalian carbonic anhydrases

Cited by 30 publications

References 35 publications

Phenols and Polyphenols as Carbonic Anhydrase Inhibitors

Phenols and Polyphenols as Carbonic Anhydrase Inhibitors

Inhibition ofβ-carbonic anhydrases fromBrucella suiswithC-cinnamoyl glycosides incorporating the phenol moiety

Anti-tubercular and antioxidant activities of C-glycosyl carbonic anhydrase inhibitors: towards the development of novel chemotherapeutic agents against Mycobacterium tuberculosis

Contact Info

Product

Resources

About