2-((4-Chloro-2-hydroxy-3-(isopropylsulfonyl)phenyl)amino)-1,5-dihydro-4H-imidazol-4-one

ID: ALA4765070

PubChem CID: 162662122

Max Phase: Preclinical

Molecular Formula: C12H14ClN3O4S

Molecular Weight: 331.78

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)S(=O)(=O)c1c(Cl)ccc(NC2=NC(=O)CN2)c1O

Standard InChI:  InChI=1S/C12H14ClN3O4S/c1-6(2)21(19,20)11-7(13)3-4-8(10(11)18)15-12-14-5-9(17)16-12/h3-4,6,18H,5H2,1-2H3,(H2,14,15,16,17)

Standard InChI Key:  JKZVWFJKEKXZJP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   32.7832   -8.5142    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.3732   -7.7970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9591   -8.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4952   -7.2742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4941   -8.1015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2088   -8.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9252   -8.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9223   -7.2706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2070   -6.8615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7790   -6.8670    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   32.7782   -9.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0614   -9.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4902   -9.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2065   -9.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6406   -8.5146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3552   -8.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1119   -8.4409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6642   -7.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2520   -7.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4451   -7.2846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5900   -6.3560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  4 10  1  0
  5  1  1  0
  1 11  1  0
 11 12  1  0
 11 13  1  0
  6 14  1  0
  7 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  2  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4765070

   ---

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: 331.78

Molecular Weight (Monoisotopic): 331.0394

AlogP: 1.13

#Rotatable Bonds: 3

Polar Surface Area: 107.86

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.30

CX Basic pKa: 3.78

CX LogP: 1.33

CX LogD: 0.25

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.72

Np Likeness Score: -0.88

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