3-Bromophenyl-4-(3-Butyl-2-oxoimidazolidin-1-yl)benzenesulfonate

ID: ALA4089342

PubChem CID: 71532408

Max Phase: Preclinical

Molecular Formula: C19H21BrN2O4S

Molecular Weight: 453.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN1CCN(c2ccc(S(=O)(=O)Oc3cccc(Br)c3)cc2)C1=O

Standard InChI:  InChI=1S/C19H21BrN2O4S/c1-2-3-11-21-12-13-22(19(21)23)16-7-9-18(10-8-16)27(24,25)26-17-6-4-5-15(20)14-17/h4-10,14H,2-3,11-13H2,1H3

Standard InChI Key:  ZPFBVUCXEAJUMK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    7.9325   -3.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3453   -4.5193    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7537   -3.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2266   -4.9361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2254   -5.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9335   -6.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431   -5.7552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6403   -4.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9317   -4.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0579   -4.9217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7771   -4.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4695   -4.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1882   -4.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2122   -3.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5116   -3.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7958   -3.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5174   -6.1637    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7738   -5.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2265   -6.4409    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6346   -7.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4340   -6.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036   -5.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4139   -6.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9330   -7.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1204   -6.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -6.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8836   -5.0050    0.0000 Br  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  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8  2  1  0
  2 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  5 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  1  0
 18 22  2  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 13 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089342

   (3-Bromophenyl) 4-(3-butyl-2-oxoimidazolidin-1-yl)benzenesulfonate

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: 453.36

Molecular Weight (Monoisotopic): 452.0405

AlogP: 4.26

#Rotatable Bonds: 7

Polar Surface Area: 66.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.33

CX LogD: 4.33

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -1.50

References

1. Fortin S, Charest-Morin X, Turcotte V, Lauvaux C, Lacroix J, Côté MF, Gobeil S, C-Gaudreault R..  (2017)  Activation of Phenyl 4-(2-Oxo-3-alkylimidazolidin-1-yl)benzenesulfonates Prodrugs by CYP1A1 as New Antimitotics Targeting Breast Cancer Cells.,  60  (12): [PMID:28535350] [10.1021/acs.jmedchem.7b00343]

Source

Source(1):

• Scientific Literature