4-[3-(2-Fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ol

ID: ALA1083083

PubChem CID: 24937759

Max Phase: Preclinical

Molecular Formula: C17H20FN3O3S

Molecular Weight: 365.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNCC(O)CCN1c2ccccc2N(c2ccccc2F)S1(=O)=O

Standard InChI:  InChI=1S/C17H20FN3O3S/c1-19-12-13(22)10-11-20-16-8-4-5-9-17(16)21(25(20,23)24)15-7-3-2-6-14(15)18/h2-9,13,19,22H,10-12H2,1H3

Standard InChI Key:  PHSDSMUCNUCJGQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   16.9819   -5.4916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9807   -6.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6956   -6.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6938   -5.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4091   -5.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4094   -6.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1999   -6.5749    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6882   -5.9031    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.1994   -5.2310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5966   -7.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1677   -8.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5647   -8.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3904   -8.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8175   -8.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4181   -7.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8433   -6.6036    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   20.0958   -5.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4000   -6.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6042   -4.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4291   -4.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8340   -3.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6590   -3.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0639   -3.0593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8888   -3.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4140   -3.0749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 11 12  1  0
 21 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083083

   2,1,3-Benzothiadiazole-1(3H)-propanol, 3-(2-fluorophenyl)-alpha-[(methylamino)methyl]-, 2,2-dioxide, (alphaS)-

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: 365.43

Molecular Weight (Monoisotopic): 365.1209

AlogP: 2.00

#Rotatable Bonds: 6

Polar Surface Area: 72.88

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.92

CX LogP: 1.11

CX LogD: -1.33

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.82

Np Likeness Score: -0.53

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