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6-{4-[4-(1H-Benzoimidazol-2-yl)-piperidin-1-ylmethyl]-phenyl}-5-phenyl-nicotinonitrile

ID: ALA369094

PubChem CID: 11454186

Max Phase: Preclinical

Molecular Formula: C31H27N5

Molecular Weight: 469.59

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  N#Cc1cnc(-c2ccc(CN3CCC(c4nc5ccccc5[nH]4)CC3)cc2)c(-c2ccccc2)c1

Standard InChI:  InChI=1S/C31H27N5/c32-19-23-18-27(24-6-2-1-3-7-24)30(33-20-23)25-12-10-22(11-13-25)21-36-16-14-26(15-17-36)31-34-28-8-4-5-9-29(28)35-31/h1-13,18,20,26H,14-17,21H2,(H,34,35)

Standard InChI Key:  ORBNIMIXUBKTHN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
    3.0161   -0.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0659   -0.8952    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7812    0.2356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6910    0.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3880    0.6198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7291   -0.6535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8576   -1.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3024   -0.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6583   -1.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252    1.2597    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8958   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    0.3700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9599    0.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4640   -1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1651   -0.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0363   -1.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1270    0.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2283    1.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9348    1.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2671    0.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3487    1.1942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5884   -0.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6559    1.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8871    0.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5109    1.3216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5364    0.4969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037    1.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2369   -1.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1265   -0.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0743   -1.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3054   -0.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5016   -1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0610   -1.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123   -1.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3813   -2.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6506   -1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4 13  1  0
  5  4  2  0
  6  4  1  0
  7  2  1  0
  8  3  1  0
  9 11  3  0
 10 24  1  0
 11 15  1  0
 12  1  1  0
 13 19  1  0
 14  6  2  0
 15 14  1  0
 16  6  1  0
 17  5  1  0
 18 10  1  0
 19 27  2  0
 20 26  1  0
 21 12  1  0
 22 12  1  0
 23 21  1  0
 24 22  1  0
 25 18  1  0
 26 25  2  0
 27 25  1  0
 28  7  1  0
 29  8  1  0
 30 16  2  0
 31 16  1  0
 32 29  2  0
 33 28  2  0
 34 31  2  0
 35 30  1  0
 36 34  1  0
  7  8  2  0
 23 10  1  0
 33 32  1  0
 13 20  2  0
 15 17  2  0
 36 35  2  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: 469.59Molecular Weight (Monoisotopic): 469.2266AlogP: 6.54#Rotatable Bonds: 5
Polar Surface Area: 68.60Molecular Species: BASEHBA: 4HBD: 1
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: 12.39CX Basic pKa: 9.17CX LogP: 5.91CX LogD: 4.13
Aromatic Rings: 5Heavy Atoms: 36QED Weighted: 0.32Np Likeness Score: -1.28

References

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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]
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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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