Phenethyl 4-ethyl-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-carboxylate 1,1-dioxide

ID: ALA3221020

PubChem CID: 90667517

Max Phase: Preclinical

Molecular Formula: C18H20N2O4S

Molecular Weight: 360.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN1CNS(=O)(=O)c2cc(C(=O)OCCc3ccccc3)ccc21

Standard InChI:  InChI=1S/C18H20N2O4S/c1-2-20-13-19-25(22,23)17-12-15(8-9-16(17)20)18(21)24-11-10-14-6-4-3-5-7-14/h3-9,12,19H,2,10-11,13H2,1H3

Standard InChI Key:  QBYVRVYJBNQUNC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   19.3208  -25.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0300  -26.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7362  -25.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0331  -26.9790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4474  -26.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4362  -24.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7335  -24.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1505  -24.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1506  -25.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8577  -26.1622    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.5691  -25.7539    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5690  -24.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8574  -24.5204    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8561  -23.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2747  -26.7362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2611  -26.8641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5632  -23.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6146  -26.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9054  -25.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9023  -24.9440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6093  -24.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6065  -23.7219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8968  -23.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1883  -23.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1945  -24.5459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  2  0
  5  9  1  0
  8  6  1  0
  6  7  2  0
  7  3  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  2  0
 10 16  2  0
 14 17  1  0
  1 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3221020

   2-Phenylethyl 4-ethyl-1,1-dioxo-2,3-dihydro-1lambda6,2,4-benzothiadiazine-7-carboxylate

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: 360.44

Molecular Weight (Monoisotopic): 360.1144

AlogP: 2.16

#Rotatable Bonds: 5

Polar Surface Area: 75.71

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: ┄

CX LogP: 3.22

CX LogD: 3.22

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: -0.61

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