4-Methyl-2-(3-phenylthioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid

ID: ALA4778886

PubChem CID: 162661251

Max Phase: Preclinical

Molecular Formula: C17H18N2O2S2

Molecular Weight: 346.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1CCCc2sc(NC(=S)Nc3ccccc3)c(C(=O)O)c21

Standard InChI:  InChI=1S/C17H18N2O2S2/c1-10-6-5-9-12-13(10)14(16(20)21)15(23-12)19-17(22)18-11-7-3-2-4-8-11/h2-4,7-8,10H,5-6,9H2,1H3,(H,20,21)(H2,18,19,22)

Standard InChI Key:  NTFPGWYEOQIDHA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    8.7958  -23.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7958  -23.8581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5078  -24.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5078  -22.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2197  -23.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2197  -23.8591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0054  -24.1144    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.4909  -23.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0054  -22.7780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5078  -21.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2604  -21.9933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7083  -21.3802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3159  -23.4462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7284  -24.1606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5534  -24.1606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3159  -24.8751    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.9659  -23.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0673  -21.8218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7913  -23.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2038  -22.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7912  -22.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9620  -22.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5533  -22.7361    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
  4 10  1  0
  9 11  1  0
 11 12  2  0
  8 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 11 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4778886

   ---

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: 346.48

Molecular Weight (Monoisotopic): 346.0810

AlogP: 4.70

#Rotatable Bonds: 3

Polar Surface Area: 61.36

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.75

CX Basic pKa: ┄

CX LogP: 6.13

CX LogD: 2.85

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.70

Np Likeness Score: -1.27

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