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6-[4-(4-Benzoimidazol-1-yl-piperidin-1-ylmethyl)-phenyl]-5-phenyl-nicotinonitrile

ID: ALA361391

PubChem CID: 11374804

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(n4cnc5ccccc54)CC3)cc2)c(-c2ccccc2)c1

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

Standard InChI Key:  SAMGJCKBKBTGPW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
    3.1077    0.6872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8441    1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4174    0.4627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5997    0.4452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3363    0.8377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5676   -0.3834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2269   -0.1296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4458   -1.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3718    1.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9117    1.8322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0373   -0.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7083   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9123    0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719   -0.8235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9998   -0.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3398    1.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6755    0.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8479   -0.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9480    1.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1755    2.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1761    0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9482    1.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5203    1.7725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    2.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4801    0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7011   -0.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3251   -1.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1441   -0.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -1.5885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9852   -1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7996   -1.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4162   -0.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0799   -1.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3839   -1.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4 13  1  0
  5  4  2  0
  6  4  1  0
  7  1  1  0
  8 12  3  0
  9  1  1  0
 10 21  1  0
 11  7  2  0
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 13 23  2  0
 14  6  2  0
 15 14  1  0
 16  9  1  0
 17  9  1  0
 18  6  1  0
 19  5  1  0
 20 16  1  0
 21 17  1  0
 22 10  1  0
 23 27  1  0
 24 26  2  0
 25 22  1  0
 26 25  1  0
 27 25  2  0
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 29 11  1  0
 30 18  1  0
 31 18  2  0
 32 28  2  0
 33 32  1  0
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  3 11  1  0
 20 10  1  0
 33 29  2  0
 24 13  1  0
 15 19  2  0
 36 34  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: 469.59Molecular Weight (Monoisotopic): 469.2266AlogP: 6.47#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: 9.02CX LogP: 5.55CX LogD: 3.92
Aromatic Rings: 5Heavy Atoms: 36QED Weighted: 0.30Np Likeness Score: -1.13

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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