ISA-2011B   Click here for help

GtoPdb Ligand ID: 8444

Compound class: Synthetic organic
Comment: Patent search with this structure reveals SCHEMBL10020974 ID matching a structure (Analogue 1) in patent WO2010149944 [3]. ISA-2011B is being evaluated pre-clinically as a potential anti-prostate cancer therapeutic [5].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 74.87
Molecular weight 423.1
XLogP 2.08
No. Lipinski's rules broken 0
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Canonical SMILES Clc1ccc2c(c1)c(c[nH]2)C1N2C(=O)CN(C(=O)C2Cc2c1cc1OCOc1c2)C
Isomeric SMILES Clc1ccc2c(c1)c(c[nH]2)[C@H]1N2C(=O)CN(C(=O)[C@@H]2Cc2c1cc1OCOc1c2)C
InChI InChI=1S/C22H18ClN3O4/c1-25-9-20(27)26-17(22(25)28)4-11-5-18-19(30-10-29-18)7-13(11)21(26)15-8-24-16-3-2-12(23)6-14(15)16/h2-3,5-8,17,21,24H,4,9-10H2,1H3/t17-,21-/m0/s1
1. Hennessy BT, Smith DL, Ram PT, Lu Y, Mills GB. (2005)
Exploiting the PI3K/AKT pathway for cancer drug discovery.
Nat Rev Drug Discov, 4 (12): 988-1004. [PMID:16341064]
2. Loijens JC, Anderson RA. (1996)
Type I phosphatidylinositol-4-phosphate 5-kinases are distinct members of this novel lipid kinase family.
J Biol Chem, 271 (51): 32937-43. [PMID:8955136]
3. Persson J, Larsson R, Sterner O, Johansson M. (2011)
Indolyl-substituted pyrazino-quinolines and their use for the treatment of cancer.
Patent number: WO2010149944. Assignee: Oncorel Ab.. Priority date: 25/06/2009. Publication date: 24/02/2011.
4. Saito K, Tolias KF, Saci A, Koon HB, Humphries LA, Scharenberg A, Rawlings DJ, Kinet JP, Carpenter CL. (2003)
BTK regulates PtdIns-4,5-P2 synthesis: importance for calcium signaling and PI3K activity.
Immunity, 19 (5): 669-78. [PMID:14614854]
5. Semenas J, Hedblom A, Miftakhova RR, Sarwar M, Larsson R, Shcherbina L, Johansson ME, Härkönen P, Sterner O, Persson JL. (2014)
The role of PI3K/AKT-related PIP5K1α and the discovery of its selective inhibitor for treatment of advanced prostate cancer.
Proc Natl Acad Sci USA, 111 (35): E3689-98. [PMID:25071204]