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

ID: ALA425338

PubChem CID: 11260243

Max Phase: Preclinical

Molecular Formula: C32H29N5

Molecular Weight: 483.62

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1nc2ccccc2n1C1CCN(Cc2ccc(-c3ncc(C#N)cc3-c3ccccc3)cc2)CC1

Standard InChI:  InChI=1S/C32H29N5/c1-23-35-30-9-5-6-10-31(30)37(23)28-15-17-36(18-16-28)22-24-11-13-27(14-12-24)32-29(19-25(20-33)21-34-32)26-7-3-2-4-8-26/h2-14,19,21,28H,15-18,22H2,1H3

Standard InChI Key:  BGGPIZRMKSCDID-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 37 42  0  0  0  0  0  0  0  0999 V2000
    3.7695    0.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0260    0.4761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305    0.2373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6854    0.3597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4135    0.7590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1282   -0.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6704   -0.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9355   -0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5208   -1.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2978    0.8754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8538    1.6743    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8125   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    0.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3835   -0.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1034   -0.4912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828    1.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5929    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9505   -0.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8730    0.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5587    2.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1256    2.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0164    1.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608    0.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9216    1.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5793    1.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3033    2.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5517    0.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895   -0.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2076   -1.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355   -1.6895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2456   -0.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577   -1.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6690   -1.8834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5217   -0.8261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2156   -2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5066   -1.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4 13  1  0
  5  4  2  0
  6  2  1  0
  7  4  1  0
  8  3  1  0
  9 12  3  0
 10  2  1  0
 11 20  1  0
 12 15  1  0
 13 24  2  0
 14  7  2  0
 15 14  1  0
 16 10  1  0
 17 10  1  0
 18  7  1  0
 19  5  1  0
 20 17  1  0
 21 16  1  0
 22 11  1  0
 23 27  2  0
 24 28  1  0
 25  1  1  0
 26 22  1  0
 27 26  1  0
 28 26  2  0
 29  6  1  0
 30  8  1  0
 31 18  2  0
 32 18  1  0
 33 29  2  0
 34 30  2  0
 35 32  2  0
 36 31  1  0
 37 35  1  0
  8  6  2  0
 34 33  1  0
 11 21  1  0
 13 23  1  0
 15 19  2  0
 37 36  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: 483.62Molecular Weight (Monoisotopic): 483.2423AlogP: 6.78#Rotatable Bonds: 5
Polar Surface Area: 57.74Molecular Species: BASEHBA: 5HBD:
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: 8.96CX LogP: 5.68CX LogD: 4.11
Aromatic Rings: 5Heavy Atoms: 37QED Weighted: 0.28Np Likeness Score: -1.32

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]
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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