New selective carbonic anhydrase IX inhibitors: Synthesis and pharmacological evaluation of diarylpyrazole-benzenesulfonamides

Rogez-Florent, Tiphaine; Meignan, Samuel; Foulon, Catherine; Six, Perrine; Gros, Abigaelle; Bal-Mahieu, Christine; Supuran, Claudiu T.; Scozzafava, Andrea; Frédérick, Raphaël; Masereel, Bernard; Depreux, Patrick; Lansiaux, Amélie; Goossens, Jean François; Gluszok, Sébastien; Goossens, Laurence

doi:10.1016/j.bmc.2012.10.029

Cited by 56 publications

(27 citation statements)

References 22 publications

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“…The reaction mixture was refluxed for 1 h. The formed precipitate was filtered, dried and recrystallized from ethanol to yield compound 3. All spectral data coincide with those reported [19].…”

Section: Chemistrysupporting

confidence: 74%

“…These studies revealed significant information about the binding mode of these compounds, and showed the crucial role of the sulfonamide as a zinc binding group [19] . Docking of compound 11e within the active site of hCA IX revealed the same important role of the deprotonated sulfonamide moiety, which interacts with zinc ion and the neighbor residues Leu198 and Thr199 (Fig.…”

Section: Molecular Docking Studiesmentioning

confidence: 95%

“…The same group developed similar compounds such as the cyclic form II, which selectively inhibited hCA IX (with Ki of 13e27 nM) versus hCA I/II [19]. The lead molecule of these derivatives was celecoxib III which was demonstrated to be a strong hCA IX (Ki ¼ 16 nM) and hCA II (Ki ¼ 21 nM) inhibitor by one of our groups [20].…”

Section: Introductionmentioning

confidence: 98%

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Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII

Ibrahim

Abou‐Seri

Tanç

et al. 2015

European Journal of Medicinal Chemistry

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104

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a b s t r a c tNew series of benzenesulfonamide derivatives incorporating pyrazole and isatin moieties were prepared using celecoxib as lead molecule. Biological evaluation of the target compounds was performed against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) and more precisely against the human isoforms hCA I, II (cytosolic), IX and XII (transmembrane, tumor-associated enzymes). Most of the tested compounds efficiently inhibited hCA I, II and IX, with K I s of 2.5e102 nM, being more effective than the reference drug acetazolamide. Compounds 11e, 11f, 16e and 16f were found to inhibit hCA XII with Ki of 3.7, 6.5, 5.4 and 7.2 nM, respectively. Compounds 11e and 16e, with 5-NO 2 substitution on the isatin ring, were found to be selective inhibitors of hCA IX and hCA XII. Docking studies revealed that the NO 2 group of both compounds participate in interactions with Asp132 within the hCA IX active site, and with residues Lys67 and Asp130 in hCA XII, respectively.

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Section: Chemistrysupporting

confidence: 74%

Section: Molecular Docking Studiesmentioning

confidence: 95%

See 1 more Smart Citation

Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII

Ibrahim

Abou‐Seri

Tanç

et al. 2015

European Journal of Medicinal Chemistry

Self Cite

104

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“…Interestingly, CAIX was found to contribute to cell migration and invasion by facilitating formation of focal adhesions, ion transport and pH control at the leading edge of lamellipodia of moving cells [27,28]. Currently, substantial effort is devoted to the development of potent, cancer-selective CAIX inhibitors, including monoclonal antibodies [29] and small molecule inhibitors [30][31][32].…”

Section: Introductionmentioning

confidence: 98%

Prognostic relevance of carbonic anhydrase IX expression is distinct in various subtypes of breast cancer and its silencing suppresses self-renewal capacity of breast cancer cells

Ivanova

Zandberga

Siliņa

et al. 2014

Cancer Chemother Pharmacol

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“…Among these, the anticancer activity was found to take place through a variety of mechanisms such as disruption of the microtubule assembly, cell cycle arrest in the G1 phase, functional suppression of the transcriptional activator NF-Y, angiogenesis and carbonic anhydrase inhibition [15,16]. The most prominent mechanism was the inhibition of carbonic anhydrase isozymes [32][33][34][35].…”

Section: Introductionmentioning

confidence: 98%

Design, synthesis and biological evaluation of some novel N-arylpyrazole derivatives bearing the sulfonamide moiety as cytotoxic agents

et al. 2016

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A series of novel N-arylpyrazole derivatives (4a-4l) bearing the sulfonamide moiety were synthesized by the condensation reaction of 1,3-dicarbonyl compounds with 4-hydrazinylbenzenesulfonamide. The structures of the obtained compounds were established on the basis of elemental (C, H, and N) and spectral analysis ( 1 H NMR, 13 C NMR, ESIMS, and FT-IR). These compounds were tested for their in vitro cytotoxic activity against three human tumor cell lines: MCF-7, Hela, and A549. The results showed that most of the obtained compounds exhibited promising cytotoxicity against the tested cell lines with low IC 50 values. The pyrazole derivative 4k, bearing two methoxy groups on the 3-position and 4-position of the phenyl ring, was the most effective one. Its inhibition of cell growth of MCF-7 cells was better than that of celecoxib and cisplatin.

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New selective carbonic anhydrase IX inhibitors: Synthesis and pharmacological evaluation of diarylpyrazole-benzenesulfonamides

Cited by 56 publications

References 22 publications

Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII

Isatin-pyrazole benzenesulfonamide hybrids potently inhibit tumor-associated carbonic anhydrase isoforms IX and XII

Prognostic relevance of carbonic anhydrase IX expression is distinct in various subtypes of breast cancer and its silencing suppresses self-renewal capacity of breast cancer cells

Design, synthesis and biological evaluation of some novel N-arylpyrazole derivatives bearing the sulfonamide moiety as cytotoxic agents

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