Tert-butyl (3-((6-chloro-2-hydroxy-3-((4-oxo-5-phenyl-4,5-dihydro-1H-imidazol-2-yl)amino)phenyl)sulfonyl)propyl)carbamate

ID: ALA4757674

PubChem CID: 162657065

Max Phase: Preclinical

Molecular Formula: C23H27ClN4O6S

Molecular Weight: 523.01

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CC(C)(C)OC(=O)NCCCS(=O)(=O)c1c(Cl)ccc(NC2=NC(=O)C(c3ccccc3)N2)c1O

Standard InChI: InChI=1S/C23H27ClN4O6S/c1-23(2,3)34-22(31)25-12-7-13-35(32,33)19-15(24)10-11-16(18(19)29)26-21-27-17(20(30)28-21)14-8-5-4-6-9-14/h4-6,8-11,17,29H,7,12-13H2,1-3H3,(H,25,31)(H2,26,27,28,30)

Standard InChI Key: WDGAPSJJNQFKEV-UHFFFAOYSA-N

Molfile:

 
     RDKit          2D

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   19.2718   -1.8686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8577   -2.5822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3939   -1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3926   -2.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1075   -2.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8238   -2.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8210   -1.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1057   -0.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6775   -0.9385    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   19.6768   -3.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9598   -3.8164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1052   -3.4092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5394   -2.5862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2540   -2.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0107   -2.5124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5630   -1.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.3439   -1.3562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4889   -0.4274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.3834   -1.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7146   -2.7399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5342   -2.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0203   -2.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6810   -1.4024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8623   -1.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9549   -4.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2380   -5.0496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2331   -5.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5162   -6.2828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9450   -6.2913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9400   -7.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6520   -7.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2231   -7.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9400   -7.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
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 32 33  1  0
 32 34  1  0
 32 35  1  0
M  END

Associated Targets(Human)

CXCR2 Tchem Interleukin-8 receptor B (3491 Activities)

Discover Target: CXCR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CXCR1 Tchem Interleukin-8 receptor A (2256 Activities)

Discover Target: CXCR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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: 523.01	Molecular Weight (Monoisotopic): 522.1340	AlogP: 3.37	#Rotatable Bonds: 7
Polar Surface Area: 146.19	Molecular Species: ACID	HBA: 8	HBD: 4
#RO5 Violations: 1	HBA (Lipinski): 10	HBD (Lipinski): 4	#RO5 Violations (Lipinski): 1
CX Acidic pKa: 6.31	CX Basic pKa: 3.55	CX LogP: 3.10	CX LogD: 2.02
Aromatic Rings: 2	Heavy Atoms: 35	QED Weighted: 0.32	Np Likeness Score: -0.96

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]

Tert-butyl (3-((6-chloro-2-hydroxy-3-((4-oxo-5-phenyl-4,5-dihydro-1H-imidazol-2-yl)amino)phenyl)sulfonyl)propyl)carbamate

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source