SLC-0111   Click here for help

GtoPdb Ligand ID: 10149

Synonyms: 4-fluorophenylureido-benzenesulfonamide | compound 7 [PMID: 21361354] | SLC0111
PDB Ligand
Compound class: Synthetic organic
Comment: SLC-0111 is a carbonic anhydrase (CA) IX/XII inhibitor that is being investigated for anti-neoplastic potential [1,4]. SLC-0111 is selective for the transmembrane CA isoforms IX and XII, compared to the cytosolic CA I and II isoforms. CA IX and XII are expressed predominantly in the hypoxic tumour microenvironment. Their inhibition promotes a significant antitumour/antimetastatic effect and reduces cancer stem cell numbers. The crystal structure of SLC-0111 bound to CA II has been resolved (see PDB ID 3N4B) [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 109.67
Molecular weight 309.06
XLogP 1.1
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(Nc1ccc(cc1)F)Nc1ccc(cc1)S(=O)(=O)N
Isomeric SMILES O=C(Nc1ccc(cc1)F)Nc1ccc(cc1)S(=O)(=O)N
InChI InChI=1S/C13H12FN3O3S/c14-9-1-3-10(4-2-9)16-13(18)17-11-5-7-12(8-6-11)21(15,19)20/h1-8H,(H2,15,19,20)(H2,16,17,18)
InChI Key YJQZNWPYLCNRLP-UHFFFAOYSA-N
References
1. Carta F, Vullo D, Osman SM, AlOthman Z, Supuran CT. (2017)
Synthesis and carbonic anhydrase inhibition of a series of SLC-0111 analogs.
Bioorg. Med. Chem., 25 (9): 2569-2576. [PMID:28347633]
2. Congiu C, Onnis V, Deplano A, Balboni G, Dedeoglu N, Supuran CT. (2015)
Synthesis of sulfonamides incorporating piperazinyl-ureido moieties and their carbonic anhydrase I, II, IX and XII inhibitory activity.
Bioorg. Med. Chem. Lett., 25 (18): 3850-3. [PMID:26233435]
3. Pacchiano F, Aggarwal M, Avvaru BS, Robbins AH, Scozzafava A, McKenna R, Supuran CT. (2010)
Selective hydrophobic pocket binding observed within the carbonic anhydrase II active site accommodate different 4-substituted-ureido-benzenesulfonamides and correlate to inhibitor potency.
Chem. Commun. (Camb.), 46 (44): 8371-3. [PMID:20922253]
4. Pacchiano F, Carta F, McDonald PC, Lou Y, Vullo D, Scozzafava A, Dedhar S, Supuran CT. (2011)
Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis.
J. Med. Chem., 54 (6): 1896-902. [PMID:21361354]