1-Cyclopentyl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamide

ID: ALA1090420

PubChem CID: 45378362

Max Phase: Preclinical

Molecular Formula: C16H24N2O4S

Molecular Weight: 340.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(C1CCCC1)N(S(N)(=O)=O)CC2

Standard InChI:  InChI=1S/C16H24N2O4S/c1-21-14-9-12-7-8-18(23(17,19)20)16(11-5-3-4-6-11)13(12)10-15(14)22-2/h9-11,16H,3-8H2,1-2H3,(H2,17,19,20)

Standard InChI Key:  USTNFAJVFHIJIS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   14.0041   -5.1615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0029   -5.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7177   -6.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7159   -4.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4311   -5.1578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4346   -5.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1535   -6.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8738   -5.9848    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8704   -5.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1467   -4.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5892   -6.3953    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.3025   -5.9809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1716   -7.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9965   -7.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2883   -6.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5743   -5.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2897   -4.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5755   -5.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1558   -7.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4926   -7.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7495   -8.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5744   -8.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8271   -7.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  1  0
 11 12  1  0
  2  3  1  0
 11 13  2  0
  3  6  2  0
 11 14  2  0
  1  2  2  0
  2 15  1  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
  1 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
  7 19  1  0
 19 20  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5  6  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090420

   1-cyclopentyl-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-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: 340.45

Molecular Weight (Monoisotopic): 340.1457

AlogP: 2.00

#Rotatable Bonds: 4

Polar Surface Area: 81.86

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.70

CX Basic pKa: ┄

CX LogP: 1.63

CX LogD: 1.63

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.91

Np Likeness Score: -0.06

References

1. Gitto R, Agnello S, Ferro S, De Luca L, Vullo D, Brynda J, Mader P, Supuran CT, Chimirri A..  (2010)  Identification of 3,4-Dihydroisoquinoline-2(1H)-sulfonamides as potent carbonic anhydrase inhibitors: synthesis, biological evaluation, and enzyme--ligand X-ray studies.,  53  (6): [PMID:20170095] [10.1021/jm9014026]

Source

Source(1):

• Scientific Literature