Literature DB >> 30274535

Carbonic anhydrase inhibition with a series of novel benzenesulfonamide-triazole conjugates.

Marwa G El-Gazzar1, Nessma H Nafie1, Alessio Nocentini2, Mostafa M Ghorab1, Helmi I Heiba1, Claudiu T Supuran2.   

Abstract

We report the synthesis and characterisation of a novel series of triazole benzenesulfonamide derivatives, which incorporate the general pharmacophore associated with carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The synthesised compounds were tested in vitro against four human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes, hCA I, hCA II, hCA IV and hCA IX. The obtained results showed that the tumour-associated hCA IX was the most sensitive to inhibition with the synthesised derivatives, with the triazolo-pyridine benzenesulfonamides 14, 16 and 17 being the most effective inhibitors. Some selected compounds were chosen for a single dose anti-proliferative activity testing against a panel of 57 human tumour cell lines and show some anti-proliferative activity ex vivo.

Entities:  

Keywords:  1,2,3-triazole; Carbonic anhydrase; anti-proliferative; benzenesulfonamide; hCA IX

Mesh:

Substances:

Year:  2018        PMID: 30274535      PMCID: PMC6171417          DOI: 10.1080/14756366.2018.1513927

Source DB:  PubMed          Journal:  J Enzyme Inhib Med Chem        ISSN: 1475-6366            Impact factor:   5.051


  24 in total

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2.  Novel sulfonamides bearing pyrrole and pyrrolopyrimidine moieties as carbonic anhydrase inhibitors: Synthesis, cytotoxic activity and molecular modeling.

Authors:  Mostafa M Ghorab; Mariangela Ceruso; Mansour S Alsaid; Yassin M Nissan; Reem K Arafa; Claudiu T Supuran
Journal:  Eur J Med Chem       Date:  2014-09-19       Impact factor: 6.514

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Journal:  Eur J Med Chem       Date:  2010-05-12       Impact factor: 6.514

5.  Discovery of New Sulfonamide Carbonic Anhydrase IX Inhibitors Incorporating Nitrogenous Bases.

Authors:  Alessio Nocentini; Silvia Bua; Carrie L Lomelino; Robert McKenna; Marta Menicatti; Gianluca Bartolucci; Barbara Tenci; Lorenzo Di Cesare Mannelli; Carla Ghelardini; Paola Gratteri; Claudiu T Supuran
Journal:  ACS Med Chem Lett       Date:  2017-11-21       Impact factor: 4.345

6.  The role of carbonic anhydrase 9 in regulating extracellular and intracellular ph in three-dimensional tumor cell growths.

Authors:  Pawel Swietach; Shalini Patiar; Claudiu T Supuran; Adrian L Harris; Richard D Vaughan-Jones
Journal:  J Biol Chem       Date:  2009-05-19       Impact factor: 5.157

7.  Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through retro-aza-Michael//aza-Michael Isomerizations.

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Review 8.  Inhibition of carbonic anhydrase IX targets primary tumors, metastases, and cancer stem cells: Three for the price of one.

Authors:  Claudiu T Supuran; Vincenzo Alterio; Anna Di Fiore; Katia D' Ambrosio; Fabrizio Carta; Simona Maria Monti; Giuseppina De Simone
Journal:  Med Res Rev       Date:  2018-04-10       Impact factor: 12.944

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10.  Synthesis and Antimicrobial Activity of 4-Substituted 1,2,3-Triazole-Coumarin Derivatives.

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Journal:  Molecules       Date:  2018-01-18       Impact factor: 4.411

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2.  The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation.

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Journal:  Antibiotics (Basel)       Date:  2022-04-27

3.  Bioorganometallic derivatives of 4-hydrazino-benzenesulphonamide as carbonic anhydrase inhibitors: synthesis, characterisation and biological evaluation.

Authors:  Jeremie Brichet; Rodrigo Arancibia; Emanuela Berrino; Claudiu T Supuran
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

4.  Inhibition survey with phenolic compounds against the δ- and η-class carbonic anhydrases from the marine diatom thalassiosira weissflogii and protozoan Plasmodium falciparum.

Authors:  Siham A Alissa; Hanan A Alghulikah; Zeid A ALOthman; Sameh M Osman; Sonia Del Prete; Clemente Capasso; Alessio Nocentini; Claudiu T Supuran
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

5.  7-Acylamino-3H-1,2-benzoxathiepine 2,2-dioxides as new isoform-selective carbonic anhydrase IX and XII inhibitors.

Authors:  Aleksandrs Pustenko; Alessio Nocentini; Anastasija Balašova; Mikhail Krasavin; Raivis Žalubovskis; Claudiu T Supuran
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

6.  Coumarins from Magydaris pastinacea as inhibitors of the tumour-associated carbonic anhydrases IX and XII: isolation, biological studies and in silico evaluation.

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Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

Review 7.  Benzothiazole derivatives as anticancer agents.

Authors:  Ali Irfan; Fozia Batool; Syeda Andleeb Zahra Naqvi; Amjad Islam; Sameh M Osman; Alessio Nocentini; Siham A Alissa; Claudiu T Supuran
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8.  Phosphonamidates are the first phosphorus-based zinc binding motif to show inhibition of β-class carbonic anhydrases from bacteria, fungi, and protozoa.

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Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

9.  A class of carbonic anhydrase IX/XII - selective carboxylate inhibitors.

Authors:  Rakia Abd Alhameed; Emanuela Berrino; Zainab Almarhoon; Ayman El-Faham; Claudiu T Supuran
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

10.  Novel insights on saccharin- and acesulfame-based carbonic anhydrase inhibitors: design, synthesis, modelling investigations and biological activity evaluation.

Authors:  Paolo Guglielmi; Giulia Rotondi; Daniela Secci; Andrea Angeli; Paola Chimenti; Alessio Nocentini; Alessandro Bonardi; Paola Gratteri; Simone Carradori; Claudiu T Supuran
Journal:  J Enzyme Inhib Med Chem       Date:  2020-12       Impact factor: 5.051

  10 in total

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