BMS-536924   

GtoPdb Ligand ID: 9386

Synonyms: BMS 536924 | BMS536924 | compound 1 [PMID: 18763755] | compound 3 [PMID: 16134929]
Compound class: Synthetic organic
Comment: BMS-536924 is an experimental inhbitor of insulin-like growth factor-1 receptor kinase which inhibits insulin-like growth factor-I receptor dependent tumour growth in vivo [2]. However, its utility is hampered by its potential to cause drug-drug interactions via inhibition of CYP3A4, and ability to increase CYP3A4 protein expression [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 105.74
Molecular weight 479.17
XLogP 4.07
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Clc1cccc(c1)C(CNC1=CC=NC(=O)C1=c1[nH]c2c([nH]1)cc(cc2C)N1CCOCC1)O
Isomeric SMILES Clc1cccc(c1)C(CNC1=CC=NC(=O)C1=c1[nH]c2c([nH]1)cc(cc2C)N1CCOCC1)O
InChI InChI=1S/C25H26ClN5O3/c1-15-11-18(31-7-9-34-10-8-31)13-20-23(15)30-24(29-20)22-19(5-6-27-25(22)33)28-14-21(32)16-3-2-4-17(26)12-16/h2-6,11-13,21,28-30,32H,7-10,14H2,1H3
InChI Key UGQMURPIMYALPH-UHFFFAOYSA-N
References
1. Velaparthi U, Wittman M, Liu P, Carboni JM, Lee FY, Attar R, Balimane P, Clarke W, Sinz MW, Hurlburt W et al.. (2008)
Discovery and evaluation of 4-(2-(4-chloro-1H-pyrazol-1-yl)ethylamino)-3-(6-(1-(3-fluoropropyl)piperidin-4-yl)-4-methyl-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one (BMS-695735), an orally efficacious inhibitor of insulin-like growth factor-1 receptor kinase with broad spectrum in vivo antitumor activity.
J. Med. Chem., 51 (19): 5897-900. [PMID:18763755]
2. Wittman M, Carboni J, Attar R, Balasubramanian B, Balimane P, Brassil P, Beaulieu F, Chang C, Clarke W, Dell J et al.. (2005)
Discovery of a (1H-benzoimidazol-2-yl)-1H-pyridin-2-one (BMS-536924) inhibitor of insulin-like growth factor I receptor kinase with in vivo antitumor activity.
J. Med. Chem., 48 (18): 5639-43. [PMID:16134929]