(R)-N-(4-chloro-3-(trifluoromethyl)phenyl)-4,4-dimethyl-6-oxo-2-(1-phenylethylamino)cyclohex-1-enecarboxamide

ID: ALA4527955

PubChem CID: 155545500

Max Phase: Preclinical

Molecular Formula: C24H24ClF3N2O2

Molecular Weight: 464.92

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: C[C@@H](NC1=C(C(=O)Nc2ccc(Cl)c(C(F)(F)F)c2)C(=O)CC(C)(C)C1)c1ccccc1

Standard InChI: InChI=1S/C24H24ClF3N2O2/c1-14(15-7-5-4-6-8-15)29-19-12-23(2,3)13-20(31)21(19)22(32)30-16-9-10-18(25)17(11-16)24(26,27)28/h4-11,14,29H,12-13H2,1-3H3,(H,30,32)/t14-/m1/s1

Standard InChI Key: URAAOBZQYLLYNK-CQSZACIVSA-N

Molfile:

 
     RDKit          2D

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   20.7409   -5.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.1558   -4.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4471   -3.9329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4487   -6.3875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.7409   -6.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7407   -7.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0333   -6.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0327   -8.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0306   -8.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7364   -9.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.4498   -8.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3265   -7.6065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6173   -8.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9111   -7.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7331  -10.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0253   -9.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1572   -7.6078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9157   -6.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2103   -6.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5001   -6.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4998   -7.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2058   -8.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6144   -8.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4447   -3.1158    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   22.8619   -3.9269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5712   -4.3329    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8589   -3.1098    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   22.8566   -4.7422    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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 29 32  1  0
M  END

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: 464.92	Molecular Weight (Monoisotopic): 464.1478	AlogP: 6.29	#Rotatable Bonds: 5
Polar Surface Area: 58.20	Molecular Species: NEUTRAL	HBA: 3	HBD: 2
#RO5 Violations: 1	HBA (Lipinski): 4	HBD (Lipinski): 2	#RO5 Violations (Lipinski): 1
CX Acidic pKa: 13.12	CX Basic pKa: ┄	CX LogP: 5.69	CX LogD: 5.69
Aromatic Rings: 2	Heavy Atoms: 32	QED Weighted: 0.51	Np Likeness Score: -1.15

References

1. Che J, Song R, Chen B, Dong X.. (2020) Targeting CXCR1/2: The medicinal potential as cancer immunotherapy agents, antagonists research highlights and challenges ahead., 185 [PMID:31732253] [10.1016/j.ejmech.2019.111853]
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]

(R)-N-(4-chloro-3-(trifluoromethyl)phenyl)-4,4-dimethyl-6-oxo-2-(1-phenylethylamino)cyclohex-1-enecarboxamide

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source