4-(3,4-Dihydroquinolin-1(2H)-ylcarbonyl)benzenesulfonamide

ID: ALA3613783

PubChem CID: 91827503

Max Phase: Preclinical

Molecular Formula: C16H16N2O3S

Molecular Weight: 316.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(C(=O)N2CCCc3ccccc32)cc1

Standard InChI:  InChI=1S/C16H16N2O3S/c17-22(20,21)14-9-7-13(8-10-14)16(19)18-11-3-5-12-4-1-2-6-15(12)18/h1-2,4,6-10H,3,5,11H2,(H2,17,20,21)

Standard InChI Key:  UVLCSZMJFKEEJN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -6.4773    7.2144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4794    6.0144    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5199    5.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2489    3.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835    5.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807    6.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1815    5.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852    3.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880    3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5175    6.6164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    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  1  0
  5  6  1  0
  5  7  2  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  6  1  0
 10  2  1  0
  2 13  1  0
  4 14  1  0
  4 17  1  0
 14 15  1  0
 15 16  1  0
 18 16  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3613783

   4-(3,4-Dihydroquinolin-1(2h)-Ylcarbonyl)benzenesulfonamide

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: 316.38

Molecular Weight (Monoisotopic): 316.0882

AlogP: 1.93

#Rotatable Bonds: 2

Polar Surface Area: 80.47

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.84

CX Basic pKa: ┄

CX LogP: 2.02

CX LogD: 2.02

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.92

Np Likeness Score: -1.68

References

1. Buemi MR, De Luca L, Ferro S, Bruno E, Ceruso M, Supuran CT, Pospíšilová K, Brynda J, Řezáčová P, Gitto R..  (2015)  Carbonic anhydrase inhibitors: Design, synthesis and structural characterization of new heteroaryl-N-carbonylbenzenesulfonamides targeting druggable human carbonic anhydrase isoforms.,  102  [PMID:26276436] [10.1016/j.ejmech.2015.07.049]

2. Buemi MR, Di Fiore A, De Luca L, Angeli A, Mancuso F, Ferro S, Monti SM, Buonanno M, Russo E, De Sarro G, De Simone G, Supuran CT, Gitto R..  (2019)  Exploring structural properties of potent human carbonic anhydrase inhibitors bearing a 4-(cycloalkylamino-1-carbonyl)benzenesulfonamide moiety.,  163  [PMID:30530195] [10.1016/j.ejmech.2018.11.073]

Source

Source(1):

• Scientific Literature