4-[(6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]benzenesulfonamide

ID: ALA3613776

PubChem CID: 122189301

Max Phase: Preclinical

Molecular Formula: C18H20N2O5S

Molecular Weight: 376.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)CN(C(=O)c1ccc(S(N)(=O)=O)cc1)CC2

Standard InChI:  InChI=1S/C18H20N2O5S/c1-24-16-9-13-7-8-20(11-14(13)10-17(16)25-2)18(21)12-3-5-15(6-4-12)26(19,22)23/h3-6,9-10H,7-8,11H2,1-2H3,(H2,19,22,23)

Standard InChI Key:  BDKQEENATAIJAQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -4.9270    8.1081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8904    7.5036    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8488    8.0995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9091    1.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9067    3.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9494    0.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2030    3.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1976    5.2575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8958    6.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5995    5.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6050    3.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8855    8.7036    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
   -1.2964   -1.4973    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
    3.8911   -1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911    1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    2.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -2.7017    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 16  1  0
 14 15  1  0
 15 18  1  0
 17 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
 20 23  1  0
 21 24  1  0
 24 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3613776

   ---

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: 376.43

Molecular Weight (Monoisotopic): 376.1093

AlogP: 1.55

#Rotatable Bonds: 4

Polar Surface Area: 98.93

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.94

CX Basic pKa: ┄

CX LogP: 1.33

CX LogD: 1.33

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.87

Np Likeness Score: -1.20

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]

Source

Source(1):

• Scientific Literature