3,5-Dibromophenyl-4-(3-Butyl-2-oxoimidazolidin-1-yl)benzenesulfonate

ID: ALA4096128

PubChem CID: 71532463

Max Phase: Preclinical

Molecular Formula: C19H20Br2N2O4S

Molecular Weight: 532.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCN1CCN(c2ccc(S(=O)(=O)Oc3cc(Br)cc(Br)c3)cc2)C1=O

Standard InChI:  InChI=1S/C19H20Br2N2O4S/c1-2-3-8-22-9-10-23(19(22)24)16-4-6-18(7-5-16)28(25,26)27-17-12-14(20)11-15(21)13-17/h4-7,11-13H,2-3,8-10H2,1H3

Standard InChI Key:  BYPYPMJEURZIRS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    8.7332   -4.1479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1459   -4.8577    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5544   -4.1454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0273   -5.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0261   -6.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7342   -6.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4438   -6.0936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4410   -5.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7324   -4.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8586   -5.2601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5778   -4.8721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2702   -5.3016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9889   -4.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0129   -4.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3123   -3.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5965   -4.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3181   -6.5021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -6.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0272   -6.7793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4353   -7.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2347   -7.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4043   -5.3732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2146   -6.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -7.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211   -7.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5893   -6.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6843   -5.3434    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.3330   -2.8508    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
 15 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4096128

   (3,5-Dibromophenyl) 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: 532.25

Molecular Weight (Monoisotopic): 529.9511

AlogP: 5.02

#Rotatable Bonds: 7

Polar Surface Area: 66.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 5.10

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -1.25

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