Novel 2-substituted-benzimidazole-6-sulfonamides as carbonic anhydrase inhibitors: synthesis, biological evaluation against isoforms I, II, IX and XII and molecular docking studies

被引：27

作者：

Milite, Ciro ^{[1
]}

Amendola, Giorgio ^{[2
]}

Nocentini, Alessio ^{[3
]}

Bua, Silvia ^{[3
]}

Cipriano, Alessandra ^{[1
,4
]}

Barresi, Elisabetta ^{[5
]}

Feoli, Alessandra ^{[1
]}

Novellino, Ettore ^{[6
]}

Da Settimo, Federico ^{[5
]}

Supuran, Claudiu T. ^{[3
]}

Castellano, Sabrina ^{[1
]}

Cosconati, Sandro ^{[2
]}

Taliani, Sabrina ^{[5
]}

机构：

[1] Univ Salerno, Dept Pharm, Epigenet Med Chem Lab, Via Giovanni Paolo II 132, I-84084 Fisciano, Salerno, Italy

[2] Univ Campania Luigi Vanvitelli, DiSTABiF, Via Vivaldi 43, I-81100 Caserta, Italy

[3] Univ Firenze, NEUROFARBA Dept, Sez Sci Farmaceut & Nutraceut, Florence, Italy

[4] Univ Salerno, PhD Program Drug Discovery & Dev, Fisciano, SA, Italy

[5] Univ Pisa, Dept Pharm, Pisa, Italy

[6] Univ Federico II Naples, Dept Pharm, Naples, Italy

来源：

JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY | 2019年 / 34卷 / 01期

关键词：

Carbonic anhydrase inhibitors; benzimidazole-sulfonamides; reduced flexibility approach; isoform-selective inhibitors; molecular docking; LOWERING AROMATIC/HETEROCYCLIC SULFONAMIDES; BASES INCORPORATING SULFONAMIDE; CRYSTAL-STRUCTURE; ISOZYME-II; DERIVATIVES; BACTERIAL; MOIETIES; TARGETS; POTENT; SERIES;

D O I：

10.1080/14756366.2019.1666836

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Inhibition of Carbonic Anhydrases (CAs) has been clinically exploited for many decades for a variety of therapeutic applications. Within a research project aimed at developing novel classes of CA inhibitors (CAIs) with a proper selectivity for certain isoforms, a series of derivatives featuring the 2-substituted-benzimidazole-6-sulfonamide scaffold, conceived as frozen analogs of Schiff bases and secondary amines previously reported in the literature as CAIs, were investigated. Enzyme inhibition assays on physiologically relevant human CA I, II, IX and XII isoforms revealed a number of potent CAIs, showing promising selectivity profiles towards the transmembrane tumor-associated CA IX and XII enzymes. Computational studies were attained to clarify the structural determinants behind the activities and selectivity profiles of the novel inhibitors.

引用

页码：1697 / 1710

页数：14

共 50 条

[1] Novel indolin-2-one-based sulfonamides as carbonic anhydrase inhibitors: Synthesis, in vitro biological evaluation against carbonic anhydrases isoforms I, II, IV and VII and molecular docking studies
Eldehna, Wagdy M.
Al-Ansary, Ghada H.
Bua, Silvia
Nocentini, Alessio
Gratteri, Paola
Altoukhy, Ayman
Ghabbour, Hazem
Ahmed, Hanaa Y.
Supuran, Claudiu T.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 127 : 521 - 530
[2] Development of sulfonamides incorporating phenylacrylamido functionalities as carbonic anhydrase isoforms I, II, IX and XII inhibitors
Angapelly, Srinivas
Ramya, P. V. Sri
Angeli, Andrea
Del Prete, Sonia
Capasso, Clemente
Arifuddin, Mohammed
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (20) : 5726 - 5732
[3] Design and synthesis of benzothiazole-6-sulfonamides acting as highly potent inhibitors of carbonic anhydrase isoforms I, II, IX and XII
Ibrahim, Diaa A.
Lasheen, Deena S.
Zaky, Maysoun Y.
Ibrahim, Amany W.
Vullo, Daniela
Ceruso, Mariangela
Supuran, Claudiu T.
Abou El Ella, Dalal A.
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (15) : 4989 - 4999
[4] Synthesis of novel acridine bis-sulfonamides with effective inhibitory activity against the carbonic anhydrase isoforms I, II, IX and XII
Esirden, Ibrahim
Ulus, Ramazan
Aday, Burak
Tanc, Muhammet
Supuran, Claudiu T.
Kaya, Muharrem
BIOORGANIC & MEDICINAL CHEMISTRY, 2015, 23 (20) : 6573 - 6580
[5] Development of novel organometallic sulfonamides with N-ethyl or N-methyl benzenesulfonamide units as potential human carbonic anhydrase I, II, IX and XII isoforms' inhibitors: Synthesis, biological evaluation and docking studies
Gallardo, Miguel
Arancibia, Rodrigo
Supuran, Claudiu T.
Nocentini, Alessio
Villaman, David
Toro, Patricia M.
Munoz-Osses, Michelle
Mascayano, Carolina
JOURNAL OF INORGANIC BIOCHEMISTRY, 2024, 260
[6] Carbonic anhydrase inhibitors: Synthesis, molecular docking, cytotoxic and inhibition of the human carbonic anhydrase isoforms I, II, IX, XII with novel benzenesulfonamides incorporating pyrrole, pyrrolopyrimidine and fused pyrrolopyrimidine moieties
Ghorab, Mostafa M.
Alsaid, Mansour S.
Ceruso, Mariangela
Nissan, Yassin M.
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (14) : 3684 - 3695
[7] Synthesis, characterization and biological evaluation of pyrazole-based benzene sulfonamides as inhibitors of human carbonic anhydrase II, IX and XII
Hussain, Tajamul
Ullah, Saif
Alrokayan, Salman
Alamery, Salman
Mohammed, Arif Ahmed
Ejaz, Syeda Abida
Aziz, Mubashir
Iqbal, Jamshed
RSC ADVANCES, 2023, 13 (27) : 18461 - 18479
[8] Carbonic anhydrase inhibitors: Synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety
Sethi, Kalyan K.
Vullo, Daniella
Verma, Saurabh M.
Tanc, Muhammet
Carta, Fabrizio
Supuran, Claudiu T.
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (19) : 5973 - 5982
[9] Design, Synthesis, and In Vitro Evaluation of Aromatic Sulfonamides as Human Carbonic Anhydrase I, II, IX, and XII Inhibitors and Their Antioxidant Activity
Mishra, K. M. Abha
Kumari, Nutan
Carta, Fabrizio
Renzi, Gioele
Supuran, Claudiu T.
Sethi, Kalyan K.
JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY, 2025, 39 (01)
[10] Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors
Rosatelli, Emiliano
Carotti, Andrea
Ceruso, Mariangela
Supuran, Claudiu T.
Gioiello, Antimo
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (15) : 3422 - 3425

← 1 2 3 4 5 →