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

ID: ALA4777868

PubChem CID: 162644160

Max Phase: Preclinical

Molecular Formula: C20H24N2O2S2

Molecular Weight: 388.56

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)c1c(NC(=S)Nc2ccccc2)sc2c1CCCC2

Standard InChI:  InChI=1S/C20H24N2O2S2/c1-20(2,3)24-18(23)16-14-11-7-8-12-15(14)26-17(16)22-19(25)21-13-9-5-4-6-10-13/h4-6,9-10H,7-8,11-12H2,1-3H3,(H2,21,22,25)

Standard InChI Key:  YORRHQVVRUIWKP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.4956  -29.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4956  -29.9414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2076  -30.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2076  -28.6997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9196  -29.1164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9195  -29.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7052  -30.1977    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.1908  -29.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7052  -28.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9602  -28.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4082  -27.4635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0158  -29.5294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4283  -30.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2533  -30.2439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0158  -30.9584    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   27.6658  -29.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4913  -29.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9037  -28.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4911  -28.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6618  -28.1052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2532  -28.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7675  -27.9065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0238  -27.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2542  -26.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8255  -26.8093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5550  -26.3939    0.0000 C   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
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 10 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4777868

   ---

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: 388.56

Molecular Weight (Monoisotopic): 388.1279

AlogP: 5.39

#Rotatable Bonds: 3

Polar Surface Area: 50.36

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.54

CX Basic pKa: ┄

CX LogP: 7.25

CX LogD: 7.25

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.55

Np Likeness Score: -1.89

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