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ID: ALA394619
Max Phase: Preclinical
Molecular Formula: C21H18N4OS
Molecular Weight: 374.47
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Cc1cccc(NC(=O)Nc2ccc(-c3csc4ccnc(N)c34)cc2)c1
Standard InChI: InChI=1S/C21H18N4OS/c1-13-3-2-4-16(11-13)25-21(26)24-15-7-5-14(6-8-15)17-12-27-18-9-10-23-20(22)19(17)18/h2-12H,1H3,(H2,22,23)(H2,24,25,26)
Standard InChI Key: GMYYMEOGFRKSFS-UHFFFAOYSA-N
Associated Targets(Human)
Vascular endothelial growth factor receptor 2 20924 Activities
Vascular endothelial growth factor receptor 1 and 2 (Flt-1 and KDR) 27 Activities
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VEGF-receptor 2 and stem cell growth factor receptor (KDR and KIT) 10 Activities
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VEGF-receptor 2 and PDGF-receptor beta (KDR and PDGFR beta) 29 Activities
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Vascular endothelial growth factor receptor 2 and tyrosine-protein kinase TIE-2 (KDR and TIE2) 14 Activities
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Serine/threonine-protein kinase MRCK-A 2525 Activities
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ALK tyrosine kinase receptor 7132 Activities
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CaM kinase II gamma 1752 Activities
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Casein kinase I gamma 2 2539 Activities
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Tyrosine-protein kinase SYK 7372 Activities
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Inhibitor of nuclear factor kappa B kinase beta subunit 5554 Activities
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Macrophage colony stimulating factor receptor 5179 Activities
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Tyrosine-protein kinase JAK2 12915 Activities
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Serine/threonine-protein kinase AKT3 3157 Activities
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Serine/threonine-protein kinase PLK4 1882 Activities
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Tyrosine-protein kinase receptor UFO 3469 Activities
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NT-3 growth factor receptor 2338 Activities
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Tyrosine-protein kinase receptor RET 6732 Activities
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Serine/threonine-protein kinase EEF2K 1246 Activities
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Protein kinase C zeta 2414 Activities
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AMP-activated protein kinase, alpha-1 subunit 2493 Activities
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BR serine/threonine-protein kinase 1 2120 Activities
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Casein kinase I isoform gamma-3 2408 Activities
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Tyrosine-protein kinase CTK 763 Activities
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PDZ-binding kinase 995 Activities
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cGMP-dependent protein kinase 1 beta 2814 Activities
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Serine/threonine-protein kinase D2 2847 Activities
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Ribosomal protein S6 kinase alpha 3 4284 Activities
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cGMP-dependent protein kinase 2 1612 Activities
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Mitogen-activated protein kinase kinase kinase kinase 4 2886 Activities
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Tyrosine-protein kinase FRK 2284 Activities
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Phosphorylase kinase gamma subunit 2 2281 Activities
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Protein kinase C delta 2953 Activities
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Ribosomal protein S6 kinase 1 4456 Activities
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Dual-specificity tyrosine-phosphorylation regulated kinase 1A 6484 Activities
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Serine/threonine-protein kinase MST2 3069 Activities
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Dual specificity protein kinase CLK2 3942 Activities
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Serine/threonine-protein kinase PLK3 1916 Activities
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LIM domain kinase 1 2329 Activities
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Serine/threonine-protein kinase Chk1 6846 Activities
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Serine/threonine-protein kinase Sgk2 2068 Activities
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Serine/threonine-protein kinase 17A 1791 Activities
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Stem cell growth factor receptor 10667 Activities
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Serine/threonine-protein kinase c-TAK1 2532 Activities
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Serine/threonine-protein kinase Aurora-A 10240 Activities
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Serine/threonine-protein kinase AKT2 4301 Activities
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Ribosomal protein S6 kinase alpha 5 3355 Activities
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Mixed lineage kinase 7 1473 Activities
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Inhibitor of nuclear factor kappa B kinase alpha subunit 3170 Activities
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Serine/threonine-protein kinase PRKX 2278 Activities
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Tyrosine-protein kinase LCK 9212 Activities
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Cyclin-dependent kinase 2 9050 Activities
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Serine/threonine-protein kinase TAO1 2019 Activities
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Tyrosine-protein kinase Srms 1588 Activities
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MAP kinase ERK2 25055 Activities
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Interleukin-1 receptor-associated kinase 4 5917 Activities
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Casein kinase II alpha 3512 Activities
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Tyrosine-protein kinase Lyn 4251 Activities
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Nerve growth factor receptor Trk-A 7922 Activities
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Serine/threonine-protein kinase PIM3 4133 Activities
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Casein kinase I delta 4546 Activities
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Fibroblast growth factor receptor 1 9149 Activities
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Glycogen synthase kinase-3 alpha 3764 Activities
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Focal adhesion kinase 1 4730 Activities
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Serine/threonine-protein kinase Aurora-B 6805 Activities
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MAP kinase-activated protein kinase 5 2831 Activities
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Death-associated protein kinase 3 2108 Activities
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Serine/threonine-protein kinase SRPK1 2359 Activities
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c-Jun N-terminal kinase 2 4655 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Proto-oncogene tyrosine-protein kinase ROS 2436 Activities
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Tyrosine-protein kinase TYK2 5029 Activities
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Tyrosine-protein kinase receptor FLT3 13481 Activities
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Tyrosine-protein kinase ABL 18331 Activities
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Cyclin-dependent kinase 5 3021 Activities
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|---|
Misshapen-like kinase 1 2339 Activities
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Tyrosine-protein kinase receptor TYRO3 2906 Activities
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MAP kinase-activated protein kinase 2 4814 Activities
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|---|
Serine/threonine-protein kinase PAK 4 3212 Activities
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|---|
Tyrosine-protein kinase FES 2339 Activities
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Interleukin-1 receptor-associated kinase 1 1749 Activities
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|---|
c-Jun N-terminal kinase 1 5038 Activities
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Casein kinase I alpha 2581 Activities
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Tyrosine-protein kinase BLK 2498 Activities
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Epidermal growth factor receptor erbB1 33727 Activities
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Mitogen-activated protein kinase kinase kinase kinase 2 2692 Activities
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Serine/threonine-protein kinase Nek4 980 Activities
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Tyrosine-protein kinase ITK/TSK 3699 Activities
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Insulin receptor 5558 Activities
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Receptor protein-tyrosine kinase erbB-2 7851 Activities
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MAP kinase signal-integrating kinase 2 3518 Activities
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Ephrin type-A receptor 2 3499 Activities
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Protein kinase C nu 2315 Activities
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Serine/threonine-protein kinase Chk2 4015 Activities
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Cell division cycle 7-related protein kinase 1385 Activities
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Testis-specific serine/threonine-protein kinase 1 2038 Activities
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Tyrosine-protein kinase BRK 2605 Activities
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Serine/threonine-protein kinase PAK 1 2601 Activities
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Protein kinase C gamma 2471 Activities
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Dual-specificity tyrosine-phosphorylation regulated kinase 3 1018 Activities
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Dual specificity tyrosine-phosphorylation-regulated kinase 4 692 Activities
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Maternal embryonic leucine zipper kinase 3491 Activities
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Ribosomal protein S6 kinase alpha 4 2104 Activities
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Tyrosine-protein kinase JAK3 8349 Activities
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Protein kinase N2 1991 Activities
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Protein tyrosine kinase 2 beta 2827 Activities
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MAP kinase-activated protein kinase 3 2212 Activities
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CaM kinase II beta 1626 Activities
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Insulin-like growth factor I receptor 8605 Activities
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Testis-specific serine/threonine-protein kinase 2 1720 Activities
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Tyrosine-protein kinase BTK 8973 Activities
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Homeodomain-interacting protein kinase 2 1644 Activities
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Serine/threonine-protein kinase PIM1 9629 Activities
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CaM kinase II delta 2813 Activities
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MAP kinase p38 delta 2605 Activities
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Tyrosine-protein kinase SRC 10310 Activities
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Hepatocyte growth factor receptor 10718 Activities
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Protein kinase C iota 2821 Activities
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Rho-associated protein kinase 2 6206 Activities
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Casein kinase I gamma 1 2496 Activities
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MAP/microtubule affinity-regulating kinase 2 2524 Activities
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Homeodomain-interacting protein kinase 4 1718 Activities
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Cyclin-dependent kinase 1 3927 Activities
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Glycogen synthase kinase-3 beta 11785 Activities
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Rho-associated protein kinase 1 4723 Activities
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cAMP-dependent protein kinase alpha-catalytic subunit 3475 Activities
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Vascular endothelial growth factor receptor 1 6262 Activities
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|---|
Serine/threonine-protein kinase PIM2 5873 Activities
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MAP kinase p38 gamma 2776 Activities
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Serine/threonine-protein kinase AKT 9192 Activities
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Tyrosine-protein kinase FER 2362 Activities
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Neurotrophic tyrosine kinase receptor type 2 3279 Activities
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3-phosphoinositide dependent protein kinase-1 3758 Activities
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Serine/threonine-protein kinase 2 1640 Activities
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CaM kinase I alpha 1664 Activities
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Dual specificity protein kinase CLK4 4053 Activities
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Mitogen-activated protein kinase kinase kinase kinase 5 1523 Activities
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Serine/threonine-protein kinase DCLK1 1025 Activities
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Fibroblast growth factor receptor 3 7811 Activities
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|---|
Receptor protein-tyrosine kinase erbB-4 2748 Activities
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Tyrosine-protein kinase FYN 5308 Activities
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Serine/threonine-protein kinase NEK2 3514 Activities
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Serine/threonine-protein kinase PLK1 28605 Activities
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Associated Targets(non-human)
Mus musculus 284745 Activities
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|---|
Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
Properties
| Molecular Weight: 374.47 | Molecular Weight (Monoisotopic): 374.1201 | AlogP: 5.50 | #Rotatable Bonds: 3 |
| Polar Surface Area: 80.04 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 3 |
| #RO5 Violations: 1 | HBA (Lipinski): 5 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 11.49 | CX Basic pKa: 5.51 | CX LogP: 4.70 | CX LogD: 4.70 |
| Aromatic Rings: 4 | Heavy Atoms: 27 | QED Weighted: 0.44 | Np Likeness Score: -1.51 |
References
| 1. Heyman HR, Frey RR, Bousquet PF, Cunha GA, Moskey MD, Ahmed AA, Soni NB, Marcotte PA, Pease LJ, Glaser KB, Yates M, Bouska JJ, Albert DH, Black-Schaefer CL, Dandliker PJ, Stewart KD, Rafferty P, Davidsen SK, Michaelides MR, Curtin ML.. (2007) Thienopyridine urea inhibitors of KDR kinase., 17 (5): [PMID:17188869] [10.1016/j.bmcl.2006.12.015] |
| 2. PubChem BioAssay data set, |
| 3. Curtin ML, Frey RR, Heyman HR, Soni NB, Marcotte PA, Pease LJ, Glaser KB, Magoc TJ, Tapang P, Albert DH, Osterling DJ, Olson AM, Bouska JJ, Guan Z, Preusser LC, Polakowski JS, Stewart KD, Tse C, Davidsen SK, Michaelides MR.. (2012) Thienopyridine ureas as dual inhibitors of the VEGF and Aurora kinase families., 22 (9): [PMID:22465635] [10.1016/j.bmcl.2012.03.035] |
Source
Source(2):