8-hydroxy-7-(2-(6-sulfonaphthalen-2-yl)hydrazinyl)quinoline-5-sulfonic acid

ID: ALA472004

Chembl Id: CHEMBL472004

Max Phase: Preclinical

Molecular Formula: C19H13N3O7S2

Molecular Weight: 459.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-87877

Synonyms from Alternative Forms(1): NSC-87877

Canonical SMILES:  O=S(=O)(O)c1ccc2cc(/N=N/c3cc(S(=O)(=O)O)c4cccnc4c3O)ccc2c1

Standard InChI:  InChI=1S/C19H13N3O7S2/c23-19-16(10-17(31(27,28)29)15-2-1-7-20-18(15)19)22-21-13-5-3-12-9-14(30(24,25)26)6-4-11(12)8-13/h1-10,23H,(H,24,25,26)(H,27,28,29)/b22-21+

Standard InChI Key:  XGMFVZOKHBRUTL-QURGRASLSA-N

Alternative Forms

1. Parent:

   

   ALA472004

   ---

2. Alternative Forms:

   

   ALA472004

   NSC87877

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 459.46

Molecular Weight (Monoisotopic): 459.0195

AlogP: 4.00

#Rotatable Bonds: 4

Polar Surface Area: 166.58

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: -4.04

CX Basic pKa: 2.57

CX LogP: -1.05

CX LogD: -1.17

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -0.79

References

1. Geronikaki A, Eleftheriou P, Vicini P, Alam I, Dixit A, Saxena AK..  (2008)  2-Thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones as new agents with SHP-2 inhibitory action.,  51  (17): [PMID:18702480] [10.1021/jm8004306]

2. Roldós V, Carbajo RJ, Schott AK, Pineda-Lucena A, Ochoa-Callejero L, Martínez A, Ramos A, de Pascual-Teresa B..  (2012)  Identification of first proadrenomedullin N-terminal 20 peptide (PAMP) modulator by means of virtual screening and NMR interaction experiments.,  55  [PMID:22884224] [10.1016/j.ejmech.2012.07.031]

3. Park H, Kyung A, Lee H, Kang S, Yoon T, Ryu SE, Jeong DG.  (2013)  Virtual screening and biochemical evaluation of the inhibitors of dual-specificity phosphatase 26,  22  (8): [10.1007/s00044-012-0405-3]

4. Genomics of Drug Sensitity in Cancer screening data, Wellcome Trust Sanger Institute,  [10.6019/CHEMBL1201861]

5. Tautz L, Senis YA, Oury C, Rahmouni S..  (2015)  Perspective: Tyrosine phosphatases as novel targets for antiplatelet therapy.,  23  (12): [PMID:25921264] [10.1016/j.bmc.2015.03.075]

6.  (2015)  Inhibition of Shp2/PTPN11 protein tyrosine phosphatase by NSC-87877, NSC-117199 and their analogs, 

7.  (2018)  Small molecule antagonists of dusp5 and methods of use, 

8. Yuan X,Bu H,Zhou J,Yang CY,Zhang H.  (2020)  Recent Advances of SHP2 Inhibitors in Cancer Therapy: Current Development and Clinical Application.,  63  (20.0): [PMID:32460492] [10.1021/acs.jmedchem.0c00249]

9. Song Y, Wang S, Zhao M, Yang X, Yu B..  (2022)  Strategies Targeting Protein Tyrosine Phosphatase SHP2 for Cancer Therapy.,  65  (4.0): [PMID:35157464] [10.1021/acs.jmedchem.1c02008]

10. Kong J, Long YQ..  (2022)  Recent advances in the discovery of protein tyrosine phosphatase SHP2 inhibitors.,  13  (3.0): [PMID:35434626] [10.1039/d1md00386k]

11. Shen D, Chen W, Zhu J, Wu G, Shen R, Xi M, Sun H..  (2020)  Therapeutic potential of targeting SHP2 in human developmental disorders and cancers.,  190  [PMID:32061959] [10.1016/j.ejmech.2020.112117]

12. Tang K, Jia YN, Yu B, Liu HM..  (2020)  Medicinal chemistry strategies for the development of protein tyrosine phosphatase SHP2 inhibitors and PROTAC degraders.,  204  [PMID:32738411] [10.1016/j.ejmech.2020.112657]

13. Zhang J, Zhang Y, Qu B, Yang H, Hu S, Dong X..  (2021)  If small molecules immunotherapy comes, can the prime be far behind?,  218  [PMID:33773287] [10.1016/j.ejmech.2021.113356]

Source

Source(4):

• Scientific Literature
• Sanger Institute Genomics of Drug Sensitivity in Cancer
• BindingDB Database
• Patent Bioactivity Data