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5-Phenyl-6-{4-[(4-[1,2,3]thiadiazol-4-yl-benzylamino)-methyl]-phenyl}-nicotinonitrile

ID: ALA360333

PubChem CID: 9912061

Max Phase: Preclinical

Molecular Formula: C28H21N5S

Molecular Weight: 459.58

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  N#Cc1cnc(-c2ccc(CNCc3ccc(-c4csnn4)cc3)cc2)c(-c2ccccc2)c1

Standard InChI:  InChI=1S/C28H21N5S/c29-15-22-14-26(23-4-2-1-3-5-23)28(31-18-22)25-12-8-21(9-13-25)17-30-16-20-6-10-24(11-7-20)27-19-34-33-32-27/h1-14,18-19,30H,16-17H2

Standard InChI Key:  FWYIMAUKHHHKGK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
    5.7417   -0.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7000    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4208    0.4708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    0.4458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6958   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -0.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5458   -1.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333   -1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292    0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958    0.4833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1333   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8667    1.3208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2833    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042    1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    1.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3000    1.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2583   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9708   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5458   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2458   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5333   -1.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  3  2  2  0
  4  5  1  0
  5  1  2  0
  6  2  1  0
  7  1  1  0
  8  7  1  0
  9 10  3  0
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 30 15  1  0
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 34 33  2  0
  8  4  2  0
 24 27  2  0
 20 12  1  0
 14 16  2  0
 34 32  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: 459.58Molecular Weight (Monoisotopic): 459.1518AlogP: 6.10#Rotatable Bonds: 7
Polar Surface Area: 74.49Molecular Species: NEUTRALHBA: 6HBD: 1
#RO5 Violations: 1HBA (Lipinski): 5HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: 8.23CX LogP: 6.20CX LogD: 5.31
Aromatic Rings: 5Heavy Atoms: 34QED Weighted: 0.32Np Likeness Score: -1.36

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]
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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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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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