N-Phenyl-4-methyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-carboxamide 1,1-dioxide

ID: ALA3221021

PubChem CID: 90667518

Max Phase: Preclinical

Molecular Formula: C15H15N3O3S

Molecular Weight: 317.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CNS(=O)(=O)c2cc(C(=O)Nc3ccccc3)ccc21

Standard InChI:  InChI=1S/C15H15N3O3S/c1-18-10-16-22(20,21)14-9-11(7-8-13(14)18)15(19)17-12-5-3-2-4-6-12/h2-9,16H,10H2,1H3,(H,17,19)

Standard InChI Key:  YZAMCSKRNZUODT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   25.9148  -25.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9136  -26.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6280  -26.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3439  -26.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3410  -25.3837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6261  -24.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0535  -24.9687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.7690  -25.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4815  -24.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7722  -26.2027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.1990  -25.3785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1877  -23.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4788  -24.1461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9083  -24.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9085  -24.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6219  -25.3788    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   32.3396  -24.9668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.3395  -24.1386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6216  -23.7224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.6202  -22.8979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0336  -25.9578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.0287  -26.0869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  2  0
 11 15  1  0
 14 12  1  0
 12 13  2  0
 13  9  1  0
 14 15  2  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16 21  2  0
 16 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221021

   4-methyl-1,1-dioxo-N-phenyl-2,3-dihydro-1lambda6,2,4-benzothiadiazine-7-carboxamide

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: 317.37

Molecular Weight (Monoisotopic): 317.0834

AlogP: 1.62

#Rotatable Bonds: 2

Polar Surface Area: 78.51

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.03

CX Basic pKa: ┄

CX LogP: 1.94

CX LogD: 1.94

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.88

Np Likeness Score: -1.28

References

1. Dintilhac G, Arslan D, Dilly S, Danober L, Botez I, Lestage P, Pirotte B, de Tullio P.  (2011)  New substituted aryl esters and aryl amides of 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides as positive allosteric modulators of AMPA receptors,  2  (6): [10.1039/C1MD00069A]

Source

Source(1):

• Scientific Literature