Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors

Angeli, Andrea; Peat, Thomas S.; Bartolucci, Gianluca; Nocentini, Alessio; Supuran, Claudiu T.; Carta, Fabrizio

doi:10.1039/c6ob02299e

Cited by 29 publications

(20 citation statements)

References 33 publications

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“…14,15 As result, we recently reported the synthesis of series of functionalized selenoureido containing scaffolds which were first evaluated for their inhibitory activities against the human expressed CAs (Figure 2). [16][17][18] Then, as extension of our studies we proved that compounds of this type possessed promising inhibition profiles against the bacterial CAs, 19…”

Section: Chemistrysupporting

confidence: 57%

“…Inhibitor and enzyme solutions were preincubated together for 15 min at room temperature prior to assay, in order to allow for the formation of the E-I complex. The inhibition constants were obtained by non-linear least-squares methods using PRISM 3 and the Cheng-Prusoff equation, as reported earlier, [18][19][20][21][22]32,33 and represent the mean from at least three different determinations. All CA isofoms were recombinant ones obtained inhouse as reported earlier.…”

Section: Carbonic Anhydrase Inhibitionmentioning

confidence: 99%

“…All CA isofoms were recombinant ones obtained inhouse as reported earlier. [18][19][20][21][22]32,33 4.…”

Section: Carbonic Anhydrase Inhibitionmentioning

confidence: 99%

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Discovery of new organoselenium compounds as antileishmanial agents

Al-Tamimi

Etxebeste-Mitxeltorena

Sanmartín

et al. 2019

Bioorganic Chemistry

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We report new organoselenium compounds bearing the sulfonamide moiety as effective inhibitors of the β-isoform of Carbonic Anhydrase from the unicellular parasitic protozoan L. donovani chagasi. All derivatives were evaluated in vitro for their leishmanicidal activities against Leishmania infantum amastigotes along with their cytotoxicities in human THP-1 cells. Compounds 3e-g showed their activity in the low micromolar range with IC50 values spanning from 0.72 to 0.81 µM and selectivity indexes (SI) >8 ( for 3g SI >30), thus much higher than those observed for the reference drugs miltefosine and edelfosine. This is the first study which reports new selenoderivatives with promising leishmanicidal properties and acting as Carbonic Anhydrase inhibitors too thus paving the way to the development of innovative agents for the treatment of neglected diseases such as leishmaniasis.

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Section: Chemistrysupporting

confidence: 57%

Section: Carbonic Anhydrase Inhibitionmentioning

confidence: 99%

See 1 more Smart Citation

Discovery of new organoselenium compounds as antileishmanial agents

Al-Tamimi

Etxebeste-Mitxeltorena

Sanmartín

et al. 2019

Bioorganic Chemistry

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show abstract

“…The inhibition constants were obtained by non-linear least-squares methods using PRISM 3 and the Cheng–Prusoff equation as reported earlier, which represent the mean from at least three different determinations. All CA isoforms were recombinant proteins obtained in-house, as reported earlier [ 62 , 63 , 64 , 65 ].…”

Section: Methodsmentioning

confidence: 99%

New Sulfanilamide Derivatives Incorporating Heterocyclic Carboxamide Moieties as Carbonic Anhydrase Inhibitors

Angeli

Карцев²,

Petrou

et al. 2021

Pharmaceuticals

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Carbonic Anhydrases (CAs) are ubiquitous metalloenzymes involved in several disease conditions. There are 15 human CA (hCA) isoforms and their high homology represents a challenge for the discovery of potential drugs devoid of off-target side effects. For this reason, many synthetic and pharmacologic research efforts are underway to achieve the full pharmacological potential of CA modulators of activity. We report here a novel series of sulfanilamide derivatives containing heterocyclic carboxamide moieties which were evaluated as CA inhibitors against the physiological relevant isoforms hCA I, II, IX, and XII. Some of them showed selectivity toward isoform hCA II and hCA XII. Molecular docking was performed for some of these compounds on isoforms hCA II and XII to understand the possible interaction with the active site amino acid residues, which rationalized the reported inhibitory activity.

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“…Inhibitor and enzyme solutions were preincubated together for 15 min at room temperature prior to assay, in order to allow for the formation of the E-I complex. The inhibition constants were obtained by non-linear least-squares methods using PRISM 3 and the Cheng-Prusoff equation, as reported earlier [26][27][28][29][30][31], and represent the mean from at least three different determinations. All CA isoforms were recombinant ones obtained in-house as reported earlier [26][27][28][29][30][31].…”

Section: Carbonic Anhydrase Inhibitionmentioning

confidence: 99%

Evaluation of Thio- and Seleno-Acetamides Bearing Benzenesulfonamide as Inhibitor of Carbonic Anhydrases from Different Pathogenic Bacteria

Angeli

Pinteala²,

Maier³

et al. 2020

IJMS

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A series of 2-thio- and 2-seleno-acetamides bearing the benzenesulfonamide moiety were evaluated as Carbonic Anhydrase (CA, EC 4.2.1.1) inhibitors against different pathogenic bacteria such as the Vibrio cholerae (VchCA-α and VchCA-β), Burkholderia pseudomallei (BpsCA-β and BpsCA-γ), Mycobacterium tuberculosis (Rv3723-β) and the Salmonella enterica serovar Typhimurium (StCA2-β). The molecules represent interesting leads worth developing as innovative antibacterial agents since they possess new mechanism of action and isoform selectivity preferentially against the bacterial expressed CAs. The identification of potent and selective inhibitors of bacterial CAs may lead to tools also useful for deciphering the physiological role(s) of such proteins.

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Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors

Cited by 29 publications

References 33 publications

Discovery of new organoselenium compounds as antileishmanial agents

Discovery of new organoselenium compounds as antileishmanial agents

New Sulfanilamide Derivatives Incorporating Heterocyclic Carboxamide Moieties as Carbonic Anhydrase Inhibitors

Evaluation of Thio- and Seleno-Acetamides Bearing Benzenesulfonamide as Inhibitor of Carbonic Anhydrases from Different Pathogenic Bacteria

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