compound 12a [PMID: 29031075]   

GtoPdb Ligand ID: 9684

Compound class: Synthetic organic
Comment: Compound 12a [PMID: 29031075] is an indomethacin analogue that was rationally designed in order to optimise COX-2 selectivity [1]. Compound 12a has comparable in vitro COX-2 inhibitory activity to indomethacin and celecoxib, but has improved selectivity for COX-2 compared to celecoxib (330-fold selectivity in this study [1]). In contrast, it is > 450-fold selective for COX-2 over COX-1.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 81.59
Molecular weight 401.05
XLogP 3.56
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Clc1ccc(cc1)C(=O)n1c2ccc(cc2c2c1CCCC2=O)S(=O)(=O)C
Isomeric SMILES Clc1ccc(cc1)C(=O)n1c2ccc(cc2c2c1CCCC2=O)S(=O)(=O)C
InChI InChI=1S/C20H16ClNO4S/c1-27(25,26)14-9-10-16-15(11-14)19-17(3-2-4-18(19)23)22(16)20(24)12-5-7-13(21)8-6-12/h5-11H,2-4H2,1H3
InChI Key MITGKKFYIJJQGL-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
9-(4-chlorobenzoyl)-6-methanesulfonyl-2,3,4,9-tetrahydro-1H-carbazol-4-one
Comments
Compound 12a [PMID: 29031075] is an indomethacin analogue that was rationally designed in order to optimise COX-2 selectivity [1]. Compound 12a has comparable in vitro COX-2 inhibitory activity to indomethacin and celecoxib, but has improved selectivity for COX-2 compared to celecoxib (330-fold selectivity in this study [1]). In contrast, it is > 450-fold selective for COX-2 over COX-1.
Database Links
GtoPdb PubChem SID 348353643
PubChem CID 131801158
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