1-[(4-Methylphenyl)sulfonyl]-1H-benzotriazole

ID: ALA4071353

PubChem CID: 1380969

Max Phase: Preclinical

Molecular Formula: C13H11N3O2S

Molecular Weight: 273.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)n2nnc3ccccc32)cc1

Standard InChI:  InChI=1S/C13H11N3O2S/c1-10-6-8-11(9-7-10)19(17,18)16-13-5-3-2-4-12(13)14-15-16/h2-9H,1H3

Standard InChI Key:  IFMSDQULCNOGJS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   26.1254  -10.8711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4196  -11.2838    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.1299  -11.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1563  -10.5133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6279   -9.8458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1361   -9.1900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3752  -10.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3647   -9.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6549   -9.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9551   -9.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9696  -10.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6800  -10.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8819  -11.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0824  -11.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5446  -12.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8081  -13.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6145  -13.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1488  -12.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2709  -13.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  7  4  1  0
  4  5  1  0
  5  6  2  0
  6  8  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
  4  2  1  0
  2 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4071353

   1-Tosyl-1H-benzotriazole

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 273.32

Molecular Weight (Monoisotopic): 273.0572

AlogP: 1.98

#Rotatable Bonds: 2

Polar Surface Area: 64.85

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.74

CX LogD: 2.74

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.72

Np Likeness Score: -1.96

References

1. Singh D, Silakari O..  (2017)  Sodium hydrogen exchanger inhibitory activity of benzotriazole derivatives.,  126  [PMID:27750152] [10.1016/j.ejmech.2016.10.005]

2. Lee, Sunkyung S and 5 more authors.  2005-04-21  (5-Arylfuran-2-ylcarbonyl)guanidines as cardioprotectives through the inhibition of Na+/H+ exchanger isoform-1.  [PMID:15828827]

3. Lee, Sunkyung S and 6 more authors.  2005-06-15  4-Substituted (benzo[b]thiophene-2-carbonyl)guanidines as novel Na+/H+ exchanger isoform-1 (NHE-1) inhibitors.  [PMID:15914000]

4. Huber, John D JD and 19 more authors.  2012-08-23  Identification of a potent sodium hydrogen exchanger isoform 1 (NHE1) inhibitor with a suitable profile for chronic dosing and demonstrated cardioprotective effects in a preclinical model of myocardial infarction in the rat.  [PMID:22803959]

Source

Source(1):

• Scientific Literature