1-(Phenylsulfonyl)-1H-benzotriazole

ID: ALA4095965

Cas Number: 4106-18-7

PubChem CID: 750248

Max Phase: Preclinical

Molecular Formula: C12H9N3O2S

Molecular Weight: 259.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S(=O)(c1ccccc1)n1nnc2ccccc21

Standard InChI:  InChI=1S/C12H9N3O2S/c16-18(17,10-6-2-1-3-7-10)15-12-9-5-4-8-11(12)13-14-15/h1-9H

Standard InChI Key:  ZMGFTNXUMSRNMD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   10.9779   -4.1146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1945   -3.3192    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.3973   -3.5294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7193   -1.4659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7181   -2.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4326   -2.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4307   -1.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1458   -1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1506   -2.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9378   -2.5390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4194   -1.8679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9299   -1.2025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0046   -3.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2587   -4.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0655   -4.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6146   -3.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3513   -3.0358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5452   -2.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 10  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
M  END

Alternative Forms

1. Parent:

   

   ALA4095965

   1-(Phenylsulfonyl)-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: 259.29

Molecular Weight (Monoisotopic): 259.0415

AlogP: 1.67

#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: 2.23

CX LogD: 2.23

Aromatic Rings: 3

Heavy Atoms: 18

QED Weighted: 0.70

Np Likeness Score: -1.91

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. Pagliero RJ, Kaiser M, Brun R, Nieto MJ, Mazzieri MR..  (2017)  Lead selection of antiparasitic compounds from a focused library of benzenesulfonyl derivatives of heterocycles.,  27  (17): [PMID:28789893] [10.1016/j.bmcl.2017.07.081]

3. 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]

4. 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]

5. 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