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

ID: ALA1090418

PubChem CID: 45378360

Max Phase: Preclinical

Molecular Formula: C14H20N2O4S

Molecular Weight: 312.39

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  COc1cc2c(cc1OC)C(C1CC1)N(S(N)(=O)=O)CC2

Standard InChI:  InChI=1S/C14H20N2O4S/c1-19-12-7-10-5-6-16(21(15,17)18)14(9-3-4-9)11(10)8-13(12)20-2/h7-9,14H,3-6H2,1-2H3,(H2,15,17,18)

Standard InChI Key:  XZFBPECMSJPLSK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -3.5284   -6.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5296   -7.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8151   -7.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8169   -5.7793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1021   -6.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0986   -7.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799   -7.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6600   -7.0149    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6634   -6.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3867   -5.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0552   -7.4252    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7681   -7.0110    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623   -8.1366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622   -8.1366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2439   -7.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9576   -7.0176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2425   -5.7798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9564   -6.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776   -8.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7846   -8.9725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9601   -8.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  5  6  1  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
 20 19  1  0
 21 20  1  0
 19 21  1  0
  7  8  1  0
  8  9  1  0
M  END

Associated Targets(Human)

CA14 Tclin Carbonic anhydrase XIV (1305 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA9 Tclin Carbonic anhydrase IX (8255 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA2 Tclin Carbonic anhydrase II (17698 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CA1 Tclin Carbonic anhydrase I (13240 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 312.39Molecular Weight (Monoisotopic): 312.1144AlogP: 1.22#Rotatable Bonds: 4
Polar Surface Area: 81.86Molecular Species: NEUTRALHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: 10.70CX Basic pKa: CX LogP: 0.75CX LogD: 0.75
Aromatic Rings: 1Heavy Atoms: 21QED Weighted: 0.91Np 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