5-(3-tosylureido)pyridine-2-sulfonamide

ID: ALA3099282

PubChem CID: 73054728

Max Phase: Preclinical

Molecular Formula: C13H14N4O5S2

Molecular Weight: 370.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)NC(=O)Nc2ccc(S(N)(=O)=O)nc2)cc1

Standard InChI:  InChI=1S/C13H14N4O5S2/c1-9-2-5-11(6-3-9)24(21,22)17-13(18)16-10-4-7-12(15-8-10)23(14,19)20/h2-8H,1H3,(H2,14,19,20)(H2,16,17,18)

Standard InChI Key:  PBRJWJGMKVRIRK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    4.1530  -10.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530  -11.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675  -11.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5820  -11.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5820  -10.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8675  -10.1681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2964  -11.8181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4386  -10.1681    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7241  -10.5806    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8511   -9.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0261   -9.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0109  -11.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7254  -11.8181    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0109  -10.5806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4399  -11.4056    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1543  -11.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8524  -10.6912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0274  -10.6912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1543  -12.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8688  -13.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5833  -12.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5833  -11.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8688  -11.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2977  -13.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  1  8  1  0
  8  9  1  0
  8 10  2  0
 11  8  2  0
  7 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 18 15  2  0
 16 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 16  1  0
 21 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3099282

   5-({[(4-Methylphenyl)sulfonyl]carbamoyl}amino)pyridine-2-Sulfonamide

Molecule Features

Natural Product: No

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: 370.41

Molecular Weight (Monoisotopic): 370.0406

AlogP: 0.55

#Rotatable Bonds: 4

Polar Surface Area: 148.32

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.60

CX Basic pKa: ┄

CX LogP: 0.97

CX LogD: 0.02

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.72

Np Likeness Score: -1.77

References

1. Bozdag M, Ferraroni M, Nuti E, Vullo D, Rossello A, Carta F, Scozzafava A, Supuran CT..  (2014)  Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: solution and X-ray crystallographic studies.,  22  (1): [PMID:24300919] [10.1016/j.bmc.2013.11.016]

2. Bozdag M, Ferraroni M, Carta F, Vullo D, Lucarini L, Orlandini E, Rossello A, Nuti E, Scozzafava A, Masini E, Supuran CT..  (2014)  Structural insights on carbonic anhydrase inhibitory action, isoform selectivity, and potency of sulfonamides and coumarins incorporating arylsulfonylureido groups.,  57  (21): [PMID:25310626] [10.1021/jm501314c]

Source

Source(1):

• Scientific Literature