trans-1-((6-(1,3-thiazol-2-ylamino)pyridin-2-yl)methyl)-4-(3-(trifluoromethyl)phenoxy)cyclohexanecarboxylic acid hydrochloride

ID: ALA3930205

PubChem CID: 87251806

Max Phase: Preclinical

Molecular Formula: C23H23ClF3N3O3S

Molecular Weight: 477.51

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: Cl.O=C(O)[C@]1(Cc2cccc(Nc3nccs3)n2)CC[C@@H](Oc2cccc(C(F)(F)F)c2)CC1

Standard InChI: InChI=1S/C23H22F3N3O3S.ClH/c24-23(25,26)15-3-1-5-18(13-15)32-17-7-9-22(10-8-17,20(30)31)14-16-4-2-6-19(28-16)29-21-27-11-12-33-21;/h1-6,11-13,17H,7-10,14H2,(H,30,31)(H,27,28,29);1H/t17-,22-;

Standard InChI Key: CUZPKOJQNROUQM-UBTQVQQGSA-N

Molfile:

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   12.1308  -20.6085    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.5231  -18.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5219  -19.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2367  -19.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9531  -19.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9503  -18.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2349  -17.8740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6631  -17.8679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3792  -18.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3797  -19.1045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0915  -19.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8068  -19.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8057  -18.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0893  -17.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5213  -19.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5213  -20.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8067  -20.7480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8064  -21.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5214  -21.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2382  -21.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2350  -20.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0918  -21.9843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3776  -21.5715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2904  -20.7546    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.4836  -20.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0707  -21.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6225  -21.9101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5160  -18.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2349  -19.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5069  -17.8577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8085  -17.8744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8083  -17.0495    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.0942  -18.2871    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.0913  -17.4618    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  6  8  1  0
  9  8  1  6
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 23  2  0
 12 28  1  1
 28 29  1  0
 28 30  2  0
  2 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Associated Targets(Human)

AURKB Tchem Aurora kinase B/Inner centromere protein (233 Activities)

Discover Target: AURKB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)

Discover Target: AURKA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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

Calculated Properties

Molecular Weight: 477.51	Molecular Weight (Monoisotopic): 477.1334	AlogP: 5.94	#Rotatable Bonds: 7
Polar Surface Area: 84.34	Molecular Species: ACID	HBA: 6	HBD: 2
#RO5 Violations: 1	HBA (Lipinski): 6	HBD (Lipinski): 2	#RO5 Violations (Lipinski): 1
CX Acidic pKa: 4.11	CX Basic pKa: 2.78	CX LogP: 5.63	CX LogD: 2.77
Aromatic Rings: 3	Heavy Atoms: 33	QED Weighted: 0.44	Np Likeness Score: -0.97

References

1. (2008) Novel aminopyridine derivatives having aurora a selective inhibitory action,
2. Fancelli, Daniele D and 24 more authors. 2006-11-30 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles: identification of a potent Aurora kinase inhibitor with a favorable antitumor kinase inhibition profile. [PMID:17125279]
3. Yang, Jing J and 11 more authors. 2007-09-15 AZD1152, a novel and selective aurora B kinase inhibitor, induces growth arrest, apoptosis, and sensitization for tubulin depolymerizing agent or topoisomerase II inhibitor in human acute leukemia cells in vitro and in vivo. [PMID:17495131]
4. McDermott, Ultan U and 24 more authors. 2007-12-11 Identification of genotype-correlated sensitivity to selective kinase inhibitors by using high-throughput tumor cell line profiling. [PMID:18077425]
5. Weiss, Matthew M MM and 30 more authors. 2008-03-27 Evaluation of a series of naphthamides as potent, orally active vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors. [PMID:18324759]
6. Shiotsu, Yukimasa Y and 16 more authors. 2009-08-20 KW-2449, a novel multikinase inhibitor, suppresses the growth of leukemia cells with FLT3 mutations or T315I-mutated BCR/ABL translocation. [PMID:19541823]
7. Zarrinkar, Patrick P PP and 15 more authors. 2009-10-01 AC220 is a uniquely potent and selective inhibitor of FLT3 for the treatment of acute myeloid leukemia (AML). [PMID:19654408]
8. Shimomura, Toshiyasu T and 14 more authors. 2010-01 MK-5108, a highly selective Aurora-A kinase inhibitor, shows antitumor activity alone and in combination with docetaxel. [PMID:20053775]
9. Adams, Nicholas D ND and 31 more authors. 2010-05-27 Discovery of GSK1070916, a potent and selective inhibitor of Aurora B/C kinase. [PMID:20420387]
10. Bavetsias, Vassilios V and 21 more authors. 2010-07-22 Imidazo[4,5-b]pyridine derivatives as inhibitors of Aurora kinases: lead optimization studies toward the identification of an orally bioavailable preclinical development candidate. [PMID:20565112]
11. Payton, Marc M and 20 more authors. 2010-12-01 Preclinical evaluation of AMG 900, a novel potent and highly selective pan-aurora kinase inhibitor with activity in taxane-resistant tumor cell lines. [PMID:20935223]
12. Medina, Jesús R JR and 24 more authors. 2011-03-24 Structure-based design of potent and selective 3-phosphoinositide-dependent kinase-1 (PDK1) inhibitors. [PMID:21341675]
13. Mollard, Alexis A and 8 more authors. 2011-12-08 Design, Synthesis and Biological Evaluation of a Series of Novel Axl Kinase Inhibitors. [PMID:22247788]
14. Lawrence, Harshani R and 14 more authors. 2012-09-13 Development of o-chlorophenyl substituted pyrimidines as exceptionally potent aurora kinase inhibitors. [PMID:22803810]
15. Elkins, Jonathan M; Santaguida, Stefano; Musacchio, Andrea and Knapp, Stefan. 2012-09-13 Crystal structure of human aurora B in complex with INCENP and VX-680. [PMID:22920039]
16. Glaser, Keith B KB and 22 more authors. 2012-12 Preclinical characterization of ABT-348, a kinase inhibitor targeting the aurora, vascular endothelial growth factor receptor/platelet-derived growth factor receptor, and Src kinase families. [PMID:22935731]
17. Weïwer, Michel M and 12 more authors. 2012-12-13 A Potent and Selective Quinoxalinone-Based STK33 Inhibitor Does Not Show Synthetic Lethality in KRAS-Dependent Cells. [PMID:23256033]
18. Li, Jie J and 6 more authors. 2013-07 A thienopyrimidine derivative induces growth inhibition and apoptosis in human cancer cell lines via inhibiting Aurora B kinase activity. [PMID:23707920]
19. Shiao, Hui-Yi HY and 18 more authors. 2013-07-11 Optimization of ligand and lipophilic efficiency to identify an in vivo active furano-pyrimidine Aurora kinase inhibitor. [PMID:23808327]
20. Sampson, Peter B PB and 23 more authors. 2015-01-08 The discovery of Polo-like kinase 4 inhibitors: design and optimization of spiro[cyclopropane-1,3'[3H]indol]-2'(1'H).ones as orally bioavailable antitumor agents. [PMID:24867403]
21. Alder, Catherine M CM and 18 more authors. 2013-10-10 Identification of a Novel and Selective Series of Itk Inhibitors via a Template-Hopping Strategy. [PMID:24900590]
22. Jagtap, Ajit Dhananjay AD and 8 more authors. 2014-10-06 Novel acylureidoindolin-2-one derivatives as dual Aurora B/FLT3 inhibitors for the treatment of acute myeloid leukemia. [PMID:25089810]
23. Carry, Jean-Christophe JC and 32 more authors. 2015-01-08 SAR156497, an exquisitely selective inhibitor of aurora kinases. [PMID:25369539]
24. An, Ying Y and 7 more authors. 2016-07-01 Design and synthesis of novel benzoxazole analogs as Aurora B kinase inhibitors. [PMID:27209235]
25. Klaeger, Susan S and 47 more authors. 2017-12-01 The target landscape of clinical kinase drugs. [PMID:29191878]
26. Barker, Michael D MD and 11 more authors. 2018-11-15 Discovery of potent and selective Spleen Tyrosine Kinase inhibitors for the topical treatment of inflammatory skin disease. [PMID:30249354]
27. Narayan, Satya S and 7 more authors. 2019-01-01 ASR352, A potent anticancer agent: Synthesis, preliminary SAR, and biological activities against colorectal cancer bulk, 5-fluorouracil/oxaliplatin resistant and stem cells. [PMID:30384048]
28. Fan, Chengcheng and 7 more authors. 2020-03-15 Design, synthesis, biological evaluation of 6-(2-amino-1H-benzo[d]imidazole-6-yl)quinazolin-4(3H)-one derivatives as novel anticancer agents with Aurora kinase inhibition. [PMID:32058239]
29. Lakkaniga, Naga Rajiv and 5 more authors. 2020-10-01 Discovery of SP-96, the first non-ATP-competitive Aurora Kinase B inhibitor, for reduced myelosuppression. [PMID:32717530]

trans-1-((6-(1,3-thiazol-2-ylamino)pyridin-2-yl)methyl)-4-(3-(trifluoromethyl)phenoxy)cyclohexanecarboxylic acid hydrochloride

Names and Identifiers

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source