4-Cyclopropyl-7-(3-methoxyphenoxy)-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxide

ID: ALA4091984

Cas Number: 1314805-66-7

PubChem CID: 53304139

Max Phase: Preclinical

Molecular Formula: C17H18N2O4S

Molecular Weight: 346.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(Oc2ccc3c(c2)S(=O)(=O)NCN3C2CC2)c1

Standard InChI:  InChI=1S/C17H18N2O4S/c1-22-13-3-2-4-14(9-13)23-15-7-8-16-17(10-15)24(20,21)18-11-19(16)12-5-6-12/h2-4,7-10,12,18H,5-6,11H2,1H3

Standard InChI Key:  CTMHATKTIDUKBM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   18.7996  -11.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3912  -10.5081    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.9783  -11.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2439   -9.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2428  -10.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9576  -10.5107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9559   -8.8578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6712   -9.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6746  -10.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1141  -10.0941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.1107   -9.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3870   -8.8452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5281  -10.5098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8139  -10.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8192   -9.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1059   -8.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3901   -9.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3921  -10.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1060  -10.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3824   -8.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7854   -7.3050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9604   -7.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6788  -10.5147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9632  -10.1041    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
 18 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091984

   4-Cyclopropyl-7-(3-methoxyphenoxy)-2,3-dihydro-1$l^{6},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: 346.41

Molecular Weight (Monoisotopic): 346.0987

AlogP: 2.71

#Rotatable Bonds: 4

Polar Surface Area: 67.87

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.07

CX Basic pKa: ┄

CX LogP: 2.66

CX LogD: 2.66

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.92

Np Likeness Score: -0.61

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