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

ID: ALA3221022

PubChem CID: 90667519

Max Phase: Preclinical

Molecular Formula: C16H17N3O3S

Molecular Weight: 331.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CNS(=O)(=O)c2cc(C(=O)N(C)c3ccccc3)ccc21

Standard InChI:  InChI=1S/C16H17N3O3S/c1-18-11-17-23(21,22)15-10-12(8-9-14(15)18)16(20)19(2)13-6-4-3-5-7-13/h3-10,17H,11H2,1-2H3

Standard InChI Key:  ZVDPSAIPBDFMCR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    1.3688  -29.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677  -30.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0757  -31.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7854  -30.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7826  -29.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0739  -29.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887  -29.4497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1980  -29.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9041  -29.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010  -30.6728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6154  -29.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042  -28.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9014  -28.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3184  -28.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3186  -29.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0256  -29.8561    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7371  -29.4478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7369  -28.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0253  -28.2143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0240  -27.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4426  -30.4301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4290  -30.5580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4856  -28.6325    0.0000 C   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
  7 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221022

   N,4-dimethyl-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: 331.40

Molecular Weight (Monoisotopic): 331.0991

AlogP: 1.65

#Rotatable Bonds: 2

Polar Surface Area: 69.72

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.03

CX Basic pKa: ┄

CX LogP: 1.81

CX LogD: 1.80

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.91

Np Likeness Score: -1.40

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