4-[3-(2-Fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylbutan-1-amine

ID: ALA1085831

PubChem CID: 24937633

Max Phase: Preclinical

Molecular Formula: C17H20FN3O2S

Molecular Weight: 349.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCCCCN1c2ccccc2N(c2ccccc2F)S1(=O)=O

Standard InChI:  InChI=1S/C17H20FN3O2S/c1-19-12-6-7-13-20-16-10-4-5-11-17(16)21(24(20,22)23)15-9-3-2-8-14(15)18/h2-5,8-11,19H,6-7,12-13H2,1H3

Standard InChI Key:  YFXILLLEWBTOSN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    9.5569   -5.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5557   -6.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2706   -6.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2688   -5.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9841   -5.7213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9844   -6.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7749   -6.8082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2632   -6.1365    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.7744   -5.4643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1716   -7.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7427   -8.2343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1397   -8.9566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9654   -8.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3925   -8.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9931   -7.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4183   -6.8369    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.6708   -5.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9750   -6.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1792   -4.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0041   -4.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4090   -4.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2340   -4.0095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6389   -3.2926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4638   -3.2848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  3  1  0
 12 13  2  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  7 10  1  0
  5  4  2  0
 15 16  1  0
  6  7  1  0
  8 17  2  0
  7  8  1  0
  8 18  2  0
  8  9  1  0
  9 19  1  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  1  0
  5  6  1  0
 21 22  1  0
 10 11  2  0
 22 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085831

   4-[3-(2-Fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methylbutan-1-amine

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: 349.43

Molecular Weight (Monoisotopic): 349.1260

AlogP: 3.03

#Rotatable Bonds: 6

Polar Surface Area: 52.65

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.54

CX LogP: 2.26

CX LogD: -0.63

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.82

Np Likeness Score: -0.91

References

1. O'Neill DJ, Adedoyin A, Alfinito PD, Bray JA, Cosmi S, Deecher DC, Fensome A, Harrison J, Leventhal L, Mann C, McComas CC, Sullivan NR, Spangler TB, Uveges AJ, Trybulski EJ, Whiteside GT, Zhang P..  (2010)  Discovery of novel selective norepinephrine reuptake inhibitors: 4-[3-aryl-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ols (WYE-103231).,  53  (11): [PMID:20462211] [10.1021/jm100053t]

Source

Source(1):

• Scientific Literature