3-Hydroxy-4-((4-oxo-5-phenyl-4,5-dihydro-1H-imidazol-2-yl)amino)benzonitrile

ID: ALA4777637

PubChem CID: 162644015

Max Phase: Preclinical

Molecular Formula: C16H12N4O2

Molecular Weight: 292.30

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(NC2=NC(=O)C(c3ccccc3)N2)c(O)c1

Standard InChI:  InChI=1S/C16H12N4O2/c17-9-10-6-7-12(13(21)8-10)18-16-19-14(15(22)20-16)11-4-2-1-3-5-11/h1-8,14,21H,(H2,18,19,20,22)

Standard InChI Key:  ULOZITGKQPTPQD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   11.0983   -7.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0972   -8.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8119   -9.0025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5284   -8.5892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5256   -7.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8101   -7.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8096   -9.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2440   -9.0027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9586   -8.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7153   -8.9290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2676   -8.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8554   -7.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0485   -7.7727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1935   -6.8440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0880   -8.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4190   -9.1564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2387   -9.2433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7249   -8.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3855   -7.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5668   -7.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3844   -7.3504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6698   -6.9381    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  3  7  1  0
  4  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  9  2  0
 12 14  2  0
 11 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  3  0
  1 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777637

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 292.30

Molecular Weight (Monoisotopic): 292.0960

AlogP: 1.90

#Rotatable Bonds: 2

Polar Surface Area: 97.51

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.54

CX Basic pKa: 4.43

CX LogP: 1.95

CX LogD: 1.92

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.73

Np Likeness Score: -0.71

References

1. Che J,Wang Z,Shen Z,Zhuang W,Ying H,Hu Y,Hu Y,Xie X,Dong X.  (2021)  Discovery of 1,5-Dihydro-4H-imidazol-4-one Derivatives as Potent, Selective Antagonists of CXC Chemokine Receptor 2.,  12  (5.0): [PMID:34055234] [10.1021/acsmedchemlett.1c00113]

2. Cutshall, N S NS, Ursino, R R, Kucera, K A KA, Latham, J J and Ihle, N C NC.  2001-07-23  Nicotinamide N-oxides as CXCR2 antagonists.  [PMID:11459668]

3. Cutshall, Neil S NS, Kucera, Kristin A KA, Ursino, Rocky R, Latham, John J and Ihle, Nathan C NC.  2002-06-03  Nicotinanilides as inhibitors of neutrophil chemotaxis.  [PMID:12031332]

4. Widdowson, Katherine L KL and 14 more authors.  2004-03-11  Evaluation of potent and selective small-molecule antagonists for the CXCR2 chemokine receptor.  [PMID:14998320]

5. Karlström, Sofia S and 20 more authors.  2013-04-25  Substituted 7-amino-5-thio-thiazolo[4,5-d]pyrimidines as potent and selective antagonists of the fractalkine receptor (CX3CR1).  [PMID:23516963]

6. Bachelerie, Francoise F and 22 more authors.  2014  International Union of Basic and Clinical Pharmacology. [corrected]. LXXXIX. Update on the extended family of chemokine receptors and introducing a new nomenclature for atypical chemokine receptors.  [PMID:24218476]

7. Austin, Rupert P RP and 14 more authors.  2015-04-01  Discovery and evaluation of a novel monocyclic series of CXCR2 antagonists.  [PMID:25708618]

8. Maeda, Dean Y and 8 more authors.  2015-06-01  Boronic acid-containing CXCR1/2 antagonists: Optimization of metabolic stability, in vivo evaluation, and a proposed receptor binding model.  [PMID:25933594]

9. Miller, Bruce E and 8 more authors.  2015-06-20  The pharmacokinetics and pharmacodynamics of danirixin (GSK1325756)--a selective CXCR2 antagonist --in healthy adult subjects.  [PMID:26092545]

10. Schuler, Aaron D and 8 more authors.  2015-09-15  Boronic acid-containing aminopyridine- and aminopyrimidinecarboxamide CXCR1/2 antagonists: Optimization of aqueous solubility and oral bioavailability.  [PMID:26248802]

11. Xu, Heng H and 19 more authors.  2016-04-14  Discovery of CNS Penetrant CXCR2 Antagonists for the Potential Treatment of CNS Demyelinating Disorders.  [PMID:27096048]

12. Gege, Christian and 15 more authors.  2018-05-15  Identification and biological evaluation of thiazole-based inverse agonists of RORγt.  [PMID:29631962]

Source

Source(1):

• Scientific Literature