Ethyl-2-(3-benzoylthioureido)-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

ID: ALA4780039

PubChem CID: 162663285

Max Phase: Preclinical

Molecular Formula: C20H22N2O3S2

Molecular Weight: 402.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1c(NC(=S)NC(=O)c2ccccc2)sc2c1C(C)CCC2

Standard InChI:  InChI=1S/C20H22N2O3S2/c1-3-25-19(24)16-15-12(2)8-7-11-14(15)27-18(16)22-20(26)21-17(23)13-9-5-4-6-10-13/h4-6,9-10,12H,3,7-8,11H2,1-2H3,(H2,21,22,23,26)

Standard InChI Key:  FGIMIJPJPWNRJQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   26.3622  -18.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3622  -19.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0743  -19.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0743  -17.7790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7862  -18.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7862  -19.0216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5718  -19.2770    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.0574  -18.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5718  -17.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0743  -16.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8268  -17.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6338  -16.9844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2748  -16.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8887  -16.1998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6957  -16.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8824  -18.6087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.2949  -19.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1199  -19.3232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8824  -20.0376    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.5323  -20.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3573  -20.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7683  -20.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5926  -20.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0059  -20.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5890  -19.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7661  -19.3255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1157  -20.7519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  4 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 20 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4780039

   ---

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: 402.54

Molecular Weight (Monoisotopic): 402.1072

AlogP: 4.49

#Rotatable Bonds: 4

Polar Surface Area: 67.43

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.90

CX Basic pKa: ┄

CX LogP: 6.44

CX LogD: 6.44

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.58

Np Likeness Score: -1.46

References

1. Xue D,Chen W,Neamati N.  (2020)  Discovery, structure-activity relationship study and biological evaluation of 2-thioureidothiophene-3-carboxylates as a novel class of C-X-C chemokine receptor 2 (CXCR2) antagonists.,  204  [PMID:32829163] [10.1016/j.ejmech.2020.112387]

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