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

ID: ALA1077215

PubChem CID: 45378363

Max Phase: Preclinical

Molecular Formula: C17H26N2O4S

Molecular Weight: 354.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(C1CCCCC1)N(S(N)(=O)=O)CC2

Standard InChI:  InChI=1S/C17H26N2O4S/c1-22-15-10-13-8-9-19(24(18,20)21)17(12-6-4-3-5-7-12)14(13)11-16(15)23-2/h10-12,17H,3-9H2,1-2H3,(H2,18,20,21)

Standard InChI Key:  IQAZISQFVSXDOO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.7773  -11.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7785  -12.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0644  -12.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0662  -10.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3518  -11.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3483  -12.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6301  -12.5258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0895  -12.1091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0861  -11.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6368  -10.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042  -12.5192    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5168  -12.1052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870  -13.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111  -13.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4924  -12.5244    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2057  -12.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910  -10.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2045  -11.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6278  -13.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3371  -13.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369  -14.5846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6240  -14.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0904  -14.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918  -13.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  8 11  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077215

   1-cyclohexyl-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: 354.47

Molecular Weight (Monoisotopic): 354.1613

AlogP: 2.39

#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: 10.71

CX Basic pKa: ┄

CX LogP: 2.08

CX LogD: 2.08

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.90

Np Likeness Score: -0.08

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