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2-(1-{4-[3-Phenyl-5-(1H-tetrazol-5-yl)-pyridin-2-yl]-benzyl}-piperidin-4-yl)-1H-benzoimidazole

ID: ALA178872

PubChem CID: 11409661

Max Phase: Preclinical

Molecular Formula: C31H28N8

Molecular Weight: 512.62

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  c1ccc(-c2cc(-c3nn[nH]n3)cnc2-c2ccc(CN3CCC(c4nc5ccccc5[nH]4)CC3)cc2)cc1

Standard InChI:  InChI=1S/C31H28N8/c1-2-6-22(7-3-1)26-18-25(31-35-37-38-36-31)19-32-29(26)23-12-10-21(11-13-23)20-39-16-14-24(15-17-39)30-33-27-8-4-5-9-28(27)34-30/h1-13,18-19,24H,14-17,20H2,(H,33,34)(H,35,36,37,38)

Standard InChI Key:  HYOQFFBLOLYSDU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.4708   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7708   -1.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1500    0.7458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2208   -0.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3500   -1.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125   -0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0333    0.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3125    0.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6792    1.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625    2.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    0.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833    1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9000    2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7000   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8833   -0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6000   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9375   -0.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1750   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  8  1  0
  4  6  2  0
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  6  3  1  0
  7 12  1  0
  8 17  2  0
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  4  7  1  0
M  END

Associated Targets(Human)

AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AKT2 Tchem Serine/threonine-protein kinase AKT2 (4301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 512.62Molecular Weight (Monoisotopic): 512.2437AlogP: 5.85#Rotatable Bonds: 6
Polar Surface Area: 99.27Molecular Species: ZWITTERIONHBA: 6HBD: 2
#RO5 Violations: 2HBA (Lipinski): 8HBD (Lipinski): 2#RO5 Violations (Lipinski): 2
CX Acidic pKa: 5.76CX Basic pKa: 9.17CX LogP: 4.01CX LogD: 4.04
Aromatic Rings: 6Heavy Atoms: 39QED Weighted: 0.29Np Likeness Score: -1.23

References

1. Zhao Z, Leister WH, Robinson RG, Barnett SF, Defeo-Jones D, Jones RE, Hartman GD, Huff JR, Huber HE, Duggan ME, Lindsley CW..  (2005)  Discovery of 2,3,5-trisubstituted pyridine derivatives as potent Akt1 and Akt2 dual inhibitors.,  15  (4): [PMID:15686884] [10.1016/j.bmcl.2004.12.062]
2. Zhu, Gui-Dong GD and 19 more authors.  2006-07-01  Discovery and SAR of oxindole-pyridine-based protein kinase B/Akt inhibitors for treating cancers.  [PMID:16644221]
3. Heerding, Dirk A DA and 27 more authors.  2008-09-25  Identification of 4-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-{[(3S)-3-piperidinylmethyl]oxy}-1H-imidazo[4,5-c]pyridin-4-yl)-2-methyl-3-butyn-2-ol (GSK690693), a novel inhibitor of AKT kinase.  [PMID:18800763]
4. Hall, Matthew D and 8 more authors.  2009-05-28  Synthesis, activity, and pharmacophore development for isatin-beta-thiosemicarbazones with selective activity toward multidrug-resistant cells.  [PMID:19397322]
5. Okuzumi, Tatsuya and 6 more authors.  2009-07  Inhibitor hijacking of Akt activation.  [PMID:19465931]
6. McHardy, Tatiana and 17 more authors.  2010-03-11  Discovery of 4-amino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamides as selective, orally active inhibitors of protein kinase B (Akt).  [PMID:20151677]
7. Blake, James F JF and 15 more authors.  2010-10-01  Discovery of pyrrolopyrimidine inhibitors of Akt.  [PMID:20810279]
8. Kim, Mi-hyun MH and 6 more authors.  2011-03-15  Structure based design and syntheses of amino-1H-pyrazole amide derivatives as selective Raf kinase inhibitors in melanoma cells.  [PMID:21353571]
9. Kim, Hyangmi; Kim, Minjung; Lee, Junghun; Yu, Hana and Hah, Jung-Mi.  2011-11-15  Syntheses of phenylpyrazolodiazepin-7-ones as conformationally rigid analogs of aminopyrazole amide scaffold and their antiproliferative effects on cancer cells.  [PMID:22014755]
10. Pireddu, Roberta and 10 more authors.  2012-06-01  Pyridylthiazole-based ureas as inhibitors of Rho associated protein kinases (ROCK1 and 2).  [PMID:23275831]
11. Addie, Matt M and 21 more authors.  2013-03-14  Discovery of 4-amino-N-[(1S)-1-(4-chlorophenyl)-3-hydroxypropyl]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (AZD5363), an orally bioavailable, potent inhibitor of Akt kinases.  [PMID:23394218]
12. Cheng, Hengmiao H and 12 more authors.  2013-05-01  Structure-based design, SAR analysis and antitumor activity of PI3K/mTOR dual inhibitors from 4-methylpyridopyrimidinone series.  [PMID:23506825]
13. Brown, Andrew and 8 more authors.  2013-05-09  Monocarbonyl curcumin analogues: heterocyclic pleiotropic kinase inhibitors that mediate anticancer properties.  [PMID:23550937]
14. Dumble, Melissa M and 13 more authors.  2014  Discovery of novel AKT inhibitors with enhanced anti-tumor effects in combination with the MEK inhibitor.  [PMID:24978597]
15. Ye, Qing Q and 14 more authors.  2015-03-01  Synthesis and biological evaluation of 3-([1,2,4]triazolo[4,3-a]pyridin-3-yl)-4-(indol-3-yl)-maleimides as potent, selective GSK-3β inhibitors and neuroprotective agents.  [PMID:25662701]
16. Lapierre, Jean-Marc JM and 19 more authors.  2016-07-14  Discovery of 3-(3-(4-(1-Aminocyclobutyl)phenyl)-5-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine (ARQ 092): An Orally Bioavailable, Selective, and Potent Allosteric AKT Inhibitor.  [PMID:27305487]
17. Sugimoto, Yasuro Y and 8 more authors.  2017-04-01  Novel pyrrolopyrimidines as Mps1/TTK kinase inhibitors for breast cancer.  [PMID:28259529]
18. Liu, Yang Y and 10 more authors.  2017-09-29  Structural optimization elaborates novel potent Akt inhibitors with promising anticancer activity.  [PMID:28704757]
19. Farag, Ahmed Karam AK and 5 more authors.  2017-12-01  Novel LCK/FMS inhibitors based on phenoxypyrimidine scaffold as potential treatment for inflammatory disorders.  [PMID:29107425]
20. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]
21. Gao, Jun-Bo JB and 8 more authors.  2018-04-27  Isolation, Characterization, and Structure-Activity Relationship Analysis of Abietane Diterpenoids from Callicarpa bodinieri as Spleen Tyrosine Kinase Inhibitors.  [PMID:29578342]
22. Zhang, Daoguang D and 5 more authors.  2018-08-01  Design, synthesis and biological evaluation of AKT inhibitors bearing a piperidin-4-yl appendant.  [PMID:30151089]
23. 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]
24. Zha, Gao-Feng; Rakesh, K P; Manukumar, H M; Shantharam, C S and Long, Sihui.  2019-01-15  Pharmaceutical significance of azepane based motifs for drug discovery: A critical review.  [PMID:30469042]
25. Zhan, Wenhu W and 9 more authors.  2019-07-07  Discovery of pyrazole-thiophene derivatives as highly Potent, orally active Akt inhibitors.  [PMID:31301565]
26. Kumar, Jetta Sandeep and 12 more authors.  2020-09-01  Rosuvastatin based novel 3-substituted isocoumarins / 3-alkylidenephthalides: Ultrasound assisted synthesis and identification of new anticancer agents.  [PMID:32599323]

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