4-Cyclopropyl-7-phenoxy-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxide

ID: ALA4100668

PubChem CID: 53259006

Max Phase: Preclinical

Molecular Formula: C16H16N2O3S

Molecular Weight: 316.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S1(=O)NCN(C2CC2)c2ccc(Oc3ccccc3)cc21

Standard InChI:  InChI=1S/C16H16N2O3S/c19-22(20)16-10-14(21-13-4-2-1-3-5-13)8-9-15(16)18(11-17-22)12-6-7-12/h1-5,8-10,12,17H,6-7,11H2

Standard InChI Key:  RXFBWHUKXZCPCA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   35.3491  -17.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9407  -17.1621    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.5279  -17.8719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7936  -15.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7924  -16.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5072  -17.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5054  -15.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2207  -15.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2242  -16.7539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6637  -16.7481    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6603  -15.9150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9365  -15.4991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0776  -17.1638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3635  -16.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3687  -15.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6555  -15.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9397  -15.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9416  -16.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6556  -17.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9319  -14.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3349  -13.9590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5100  -13.9635    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
M  END

Alternative Forms

1. Parent:

   

   ALA4100668

   4-Cyclopropyl-7-phenoxy-2,3-dihydro-1lambda6,2,4-benzothiadiazine 1,1-dioxide

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: 316.38

Molecular Weight (Monoisotopic): 316.0882

AlogP: 2.70

#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: 2.82

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.95

Np Likeness Score: -0.66

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