N-Ethyl-N-phenyl-4-methyl-3,4-dihy dro-2H-1,2,4-benzothiadiazine-7-carboxamide 1,1-dioxide

ID: ALA3221023

PubChem CID: 90667520

Max Phase: Preclinical

Molecular Formula: C17H19N3O3S

Molecular Weight: 345.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(C(=O)c1ccc2c(c1)S(=O)(=O)NCN2C)c1ccccc1

Standard InChI:  InChI=1S/C17H19N3O3S/c1-3-20(14-7-5-4-6-8-14)17(21)13-9-10-15-16(11-13)24(22,23)18-12-19(15)2/h4-11,18H,3,12H2,1-2H3

Standard InChI Key:  FZZXVTZCGUESRU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    8.7153  -29.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7141  -30.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4222  -30.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1319  -30.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1290  -29.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4204  -29.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8352  -29.0040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5444  -29.4099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2506  -28.9987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5475  -30.2271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9618  -29.4100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9507  -27.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2479  -28.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6649  -28.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6650  -29.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3721  -29.4103    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.0836  -29.0020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0834  -28.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3718  -27.7685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3705  -26.9513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7891  -29.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7755  -30.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8321  -28.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5383  -27.7755    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
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221023

   N-ethyl-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: 345.42

Molecular Weight (Monoisotopic): 345.1147

AlogP: 2.04

#Rotatable Bonds: 3

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: 2.16

CX LogD: 2.16

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.92

Np Likeness Score: -1.53

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