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

ID: ALA178445

PubChem CID: 11364261

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(n4cnc5ccccc54)CC3)cc2)cc1

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

Standard InChI Key:  BUDCDMBOPKDELH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.2833   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5833   -1.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0333   -0.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1708   -1.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    0.2208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5625   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1333   -0.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500    0.8833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1333    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3625   -1.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8500   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667   -0.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4292    1.7208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1500    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375    0.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1417    2.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167    2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083    0.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4333    1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    2.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042    0.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -1.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -1.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -1.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -1.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -0.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0042   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  5  2  0
  4  1  1  0
  5  2  1  0
  6 12  1  0
  7  4  2  0
  8 18  2  0
  9 11  1  0
 10 11  2  0
 11 19  1  0
 12  2  2  0
 13  9  2  0
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 15  1  1  0
 16 24  1  0
 17 14  2  0
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 19 26  2  0
 20 15  1  0
 21 15  1  0
 22  9  1  0
 23 20  1  0
 24 21  1  0
 25 16  1  0
 26 30  1  0
 27 29  2  0
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 32 17  1  0
 33 22  2  0
 34 22  1  0
 35 31  2  0
 36 35  1  0
 37 33  1  0
 38 34  2  0
 39 38  1  0
  7 17  1  0
 23 16  1  0
 36 32  2  0
 19 27  1  0
  8 13  1  0
 39 37  2  0
  3  6  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: 5.78#Rotatable Bonds: 6
Polar Surface Area: 88.41Molecular Species: ZWITTERIONHBA: 7HBD: 1
#RO5 Violations: 2HBA (Lipinski): 8HBD (Lipinski): 1#RO5 Violations (Lipinski): 2
CX Acidic pKa: 5.75CX Basic pKa: 9.02CX LogP: 3.63CX LogD: 3.66
Aromatic Rings: 6Heavy Atoms: 39QED Weighted: 0.30Np Likeness Score: -1.10

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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