Tert-Butyl-2-(3-(3,4-dimethoxyphenyl)thioureido)-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

ID: ALA4779981

PubChem CID: 162662426

Max Phase: Preclinical

Molecular Formula: C23H30N2O4S2

Molecular Weight: 462.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(NC(=S)Nc2sc3c(c2C(=O)OC(C)(C)C)C(C)CCC3)cc1OC

Standard InChI:  InChI=1S/C23H30N2O4S2/c1-13-8-7-9-17-18(13)19(21(26)29-23(2,3)4)20(31-17)25-22(30)24-14-10-11-15(27-5)16(12-14)28-6/h10-13H,7-9H2,1-6H3,(H2,24,25,30)

Standard InChI Key:  GMPOQIKLVNCGSO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   19.8498  -15.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8498  -14.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5618  -15.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5618  -14.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2738  -14.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2737  -15.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0594  -15.5895    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.5450  -14.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0595  -14.2531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3144  -13.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7624  -12.8553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3700  -14.9213    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7825  -15.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6075  -15.6357    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3700  -16.3502    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.0200  -14.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8455  -14.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2579  -14.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8454  -13.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0160  -13.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6074  -14.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1217  -13.2983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3780  -12.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6085  -11.7976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1797  -12.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9093  -11.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5618  -13.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0853  -14.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2596  -12.7781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0846  -12.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5013  -13.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  4  1  0
  1  3  1  0
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  9 10  1  0
 10 11  2  0
  8 12  1  0
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 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
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 10 22  1  0
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  4 27  1  0
 18 28  1  0
 19 29  1  0
 29 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4779981

   ---

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: 462.64

Molecular Weight (Monoisotopic): 462.1647

AlogP: 5.97

#Rotatable Bonds: 5

Polar Surface Area: 68.82

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.49

CX Basic pKa: ┄

CX LogP: 7.22

CX LogD: 7.22

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: -1.13

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