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(S)-4-(2-(3-chlorophenyl)-2-hydroxyethylamino)-3-(6-(4-(2-hydroxyethoxy)piperidin-1-yl)-4-methyl-1H-benzo[d]imidazol-2-yl)pyridin-2(1H)-one

ID: ALA482089

PubChem CID: 135960714

Max Phase: Preclinical

Molecular Formula: C28H32ClN5O4

Molecular Weight: 538.05

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1cc(N2CCC(OCCO)CC2)cc2[nH]c(-c3c(NC[C@@H](O)c4cccc(Cl)c4)cc[nH]c3=O)nc12

Standard InChI:  InChI=1S/C28H32ClN5O4/c1-17-13-20(34-9-6-21(7-10-34)38-12-11-35)15-23-26(17)33-27(32-23)25-22(5-8-30-28(25)37)31-16-24(36)18-3-2-4-19(29)14-18/h2-5,8,13-15,21,24,35-36H,6-7,9-12,16H2,1H3,(H,32,33)(H2,30,31,37)/t24-/m1/s1

Standard InChI Key:  OMEGCBMNQDIBMF-XMMPIXPASA-N

Molfile:  

     RDKit          2D

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    7.1307   -4.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8456   -4.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8438   -2.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5591   -3.1838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5594   -4.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3499   -4.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8382   -3.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3494   -2.9268    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6599   -3.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0721   -4.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8963   -4.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3094   -3.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8922   -2.8814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0693   -2.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6546   -2.1717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8458   -5.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6591   -5.0274    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0711   -5.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6581   -6.4563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0701   -7.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6549   -7.8850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0663   -8.5992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8921   -8.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3050   -7.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8913   -7.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1300   -7.8787    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.8331   -6.4558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4135   -2.7707    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4153   -1.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7048   -1.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9880   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9862   -2.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013   -3.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -1.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5591   -1.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8461   -1.5216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490   -0.6966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11 18  1  0
  8  9  1  0
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  5  6  1  0
 21 22  2  0
 10 11  2  0
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 11 12  1  0
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  2  3  1  0
 25 26  2  0
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 25 27  1  0
  3  6  2  0
 20 28  1  6
 29 30  1  0
 13 14  1  0
  1  2  2  0
 14 15  1  0
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  8 10  1  0
  5  4  2  0
 29 34  1  0
 30 31  1  0
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  1 29  1  0
 15 16  2  0
 32 35  1  0
  6  7  1  0
 35 36  1  0
  3 17  1  0
 36 37  1  0
  7  8  2  0
 37 38  1  0
M  END

Alternative Forms

  1. Parent:

    ALA482089

    ---

Associated Targets(Human)

IGF1R Tclin Insulin-like growth factor I receptor (8605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Igf1r Insulin-like growth factor 1 receptor (35 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 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

Biocomponents

Calculated Properties

Molecular Weight: 538.05Molecular Weight (Monoisotopic): 537.2143AlogP: 4.00#Rotatable Bonds: 9
Polar Surface Area: 126.50Molecular Species: NEUTRALHBA: 7HBD: 5
#RO5 Violations: 1HBA (Lipinski): 9HBD (Lipinski): 5#RO5 Violations (Lipinski): 1
CX Acidic pKa: 9.58CX Basic pKa: 4.13CX LogP: 2.34CX LogD: 2.33
Aromatic Rings: 4Heavy Atoms: 38QED Weighted: 0.22Np Likeness Score: -0.76

References

1. Zimmermann K, Wittman MD, Saulnier MG, Velaparthi U, Langley DR, Sang X, Frennesson D, Carboni J, Li A, Greer A, Gottardis M, Attar RM, Yang Z, Balimane P, Discenza LN, Vyas D..  (2008)  Balancing oral exposure with Cyp3A4 inhibition in benzimidazole-based IGF-IR inhibitors.,  18  (14): [PMID:18572407] [10.1016/j.bmcl.2008.05.104]
2. Girnita, Ada A and 5 more authors.  2004-01-01  Cyclolignans as inhibitors of the insulin-like growth factor-1 receptor and malignant cell growth.  [PMID:14729630]
3. García-Echeverría, Carlos C and 17 more authors.  2004-03  In vivo antitumor activity of NVP-AEW541-A novel, potent, and selective inhibitor of the IGF-IR kinase.  [PMID:15050915]
4. Gable, Karissa L KL and 10 more authors.  2006-04  Diarylureas are small-molecule inhibitors of insulin-like growth factor I receptor signaling and breast cancer cell growth.  [PMID:16648580]
5. Hubbard, Robert D RD and 16 more authors.  2009-03-15  Development of multitargeted inhibitors of both the insulin-like growth factor receptor (IGF-IR) and members of the epidermal growth factor family of receptor tyrosine kinases.  [PMID:19217287]
6. Li, Rongshi; Pourpak, Alan and Morris, Stephan W.  2009-08-27  Inhibition of the insulin-like growth factor-1 receptor (IGF1R) tyrosine kinase as a novel cancer therapy approach.  [PMID:19610618]
7. Sabbatini, Peter P and 19 more authors.  2009-10  GSK1838705A inhibits the insulin-like growth factor-1 receptor and anaplastic lymphoma kinase and shows antitumor activity in experimental models of human cancers.  [PMID:19825801]
8. Liu, Xiaofeng X and 8 more authors.  2010-03-25  Discovery and SAR of thiazolidine-2,4-dione analogues as insulin-like growth factor-1 receptor (IGF-1R) inhibitors via hierarchical virtual screening.  [PMID:20178321]
9. Lesuisse, Dominique D and 17 more authors.  2011-04-15  Discovery of the first non-ATP competitive IGF-1R kinase inhibitors: advantages in comparison with competitive inhibitors.  [PMID:21441024]
10. Huang, Wei-Sheng WS and 33 more authors.  2016-05-26  Discovery of Brigatinib (AP26113), a Phosphine Oxide-Containing, Potent, Orally Active Inhibitor of Anaplastic Lymphoma Kinase.  [PMID:27144831]
11. Klaeger, Susan S and 47 more authors.  2017-12-01  The target landscape of clinical kinase drugs.  [PMID:29191878]
12. Qi, Baohui B and 11 more authors.  2019-02-01  Discovery of N1-(4-((7-(3-(4-ethylpiperazin-1-yl)propoxy)-6-methoxyquinolin-4-yl)oxy)-3,5-difluorophenyl)-N3-(2-(2,6-difluorophenyl)-4-oxothiazolidin-3-yl)urea as a multi-tyrosine kinase inhibitor for drug-sensitive and drug-resistant cancers treatment.  [PMID:30503936]
13. Yan, Guoyi and 11 more authors.  2021-02-11  Targeting Cysteine Located Outside the Active Site: An Effective Strategy for Covalent ALKi Design.  [PMID:33471528]

Source