4-Cyclopropyl-7-(2-methylphenoxy)-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxide

ID: ALA4073898

PubChem CID: 137641078

Max Phase: Preclinical

Molecular Formula: C17H18N2O3S

Molecular Weight: 330.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccccc1Oc1ccc2c(c1)S(=O)(=O)NCN2C1CC1

Standard InChI:  InChI=1S/C17H18N2O3S/c1-12-4-2-3-5-16(12)22-14-8-9-15-17(10-14)23(20,21)18-11-19(15)13-6-7-13/h2-5,8-10,13,18H,6-7,11H2,1H3

Standard InChI Key:  AYBKVNSABKVZCY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    9.0008   -5.0630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5924   -4.3504    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.1796   -5.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4450   -3.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4439   -3.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1587   -4.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1569   -2.6999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8723   -3.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8758   -3.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3155   -3.9363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3121   -3.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5882   -2.6873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7289   -4.3522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0147   -3.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0200   -3.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3067   -2.7011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908   -3.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5927   -3.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3068   -4.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5836   -1.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9907   -1.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1656   -1.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097   -5.1768    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  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 12  1  0
  9  2  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 12 20  1  0
 21 20  1  0
 22 21  1  0
 20 22  1  0
 19 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4073898

   ---

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: 330.41

Molecular Weight (Monoisotopic): 330.1038

AlogP: 3.01

#Rotatable Bonds: 3

Polar Surface Area: 58.64

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.07

CX Basic pKa: ┄

CX LogP: 3.33

CX LogD: 3.33

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.94

Np Likeness Score: -0.74

References

1. Goffin E, Drapier T, Larsen AP, Geubelle P, Ptak CP, Laulumaa S, Rovinskaja K, Gilissen J, Tullio P, Olsen L, Frydenvang K, Pirotte B, Hanson J, Oswald RE, Kastrup JS, Francotte P..  (2018)  7-Phenoxy-Substituted 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxides as Positive Allosteric Modulators of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors with Nanomolar Potency.,  61  (1): [PMID:29256599] [10.1021/acs.jmedchem.7b01323]

Source

Source(1):

• Scientific Literature