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4-((E)-(((Z)-4-cyclopropyl-2-(phenylimino)thiazol-3(2H)-yl)imino)methyl)benzene-1,2,3-triol hydrogen bromide

ID: ALA5282175

Max Phase: Preclinical

Molecular Formula: C19H18BrN3O3S

Molecular Weight: 367.43

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  Br.Oc1ccc(/C=N/n2c(C3CC3)cs/c2=N\c2ccccc2)c(O)c1O

Standard InChI:  InChI=1S/C19H17N3O3S.BrH/c23-16-9-8-13(17(24)18(16)25)10-20-22-15(12-6-7-12)11-26-19(22)21-14-4-2-1-3-5-14;/h1-5,8-12,23-25H,6-7H2;1H/b20-10+,21-19-;

Standard InChI Key:  LPBMVSPSUCLMLH-WINKVWEOSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    4.1517   -1.9419    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718    2.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    2.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    2.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454    1.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8555    0.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718    1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.8958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4307    0.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7160   -0.3419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9016   -1.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7031   -1.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352   -0.4844    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3181   -1.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0015    0.0706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7130   -0.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4277    0.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4279    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1408    1.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8556    0.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8572    0.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454   -0.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454   -1.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5718   -0.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702    1.3064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1041   -2.5454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787   -1.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  7  6  2  0
  2  7  1  0
  5  8  1  0
  8  9  2  0
 10  9  1  0
 10 11  1  0
 11 12  2  0
 13 12  1  0
  9 13  1  0
 11 14  1  0
 10 15  1  0
 15 16  2  0
 16 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 22 23  1  0
 21 24  1  0
 20 25  1  0
 26 14  1  0
 26 27  1  0
 14 27  1  0
M  END

Associated Targets(Human)

BCL2A1 Tchem Bcl-2-related protein A1 (291 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Topical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

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MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

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Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Biocomponents

Calculated Properties

Molecular Weight: 367.43Molecular Weight (Monoisotopic): 367.0991AlogP: 3.66#Rotatable Bonds: 4
Polar Surface Area: 90.34Molecular Species: NEUTRALHBA: 7HBD: 3
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 8.54CX Basic pKa: 2.29CX LogP: 4.28CX LogD: 4.25
Aromatic Rings: 3Heavy Atoms: 26QED Weighted: 0.49Np Likeness Score: -0.77

References

1. Li X, Dou J, You Q, Jiang Z..  (2021)  Inhibitors of BCL2A1/Bfl-1 protein: Potential stock in cancer therapy.,  220  [PMID:34034128] [10.1016/j.ejmech.2021.113539]
2. Nguyen, Mai M and 16 more authors.  2007-12-04  Small molecule obatoclax (GX15-070) antagonizes MCL-1 and overcomes MCL-1-mediated resistance to apoptosis.  [PMID:18040043]
3. Wei, Jun J and 12 more authors.  2009-07-23  Apogossypol derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins.  [PMID:19555126]
4. Wei, Jun J and 13 more authors.  2010-05-27  BI-97C1, an optically pure Apogossypol derivative as pan-active inhibitor of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins.  [PMID:20443627]
5. Cashman, John R and 9 more authors.  2010-11-15  Inhibition of Bfl-1 with N-aryl maleimides.  [PMID:20933419]
6. Wei, Jun J and 12 more authors.  2010-11-25  Synthesis and biological evaluation of Apogossypolone derivatives as pan-active inhibitors of antiapoptotic B-cell lymphoma/leukemia-2 (Bcl-2) family proteins.  [PMID:21033669]
7. de Araujo, Aline Dantas AD, Lim, Junxian J, Good, Andrew C AC, Skerlj, Renato T RT and Fairlie, David P DP.  2017-01-12  Electrophilic Helical Peptides That Bond Covalently, Irreversibly, and Selectively in a Protein-Protein Interaction Site.  [PMID:28105269]
8. Kump, Karson J and 15 more authors.  2020-03-12  Discovery and Characterization of 2,5-Substituted Benzoic Acid Dual Inhibitors of the Anti-apoptotic Mcl-1 and Bfl-1 Proteins.  [PMID:31971799]

Source