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

ID: ALA4097043

PubChem CID: 71532460

Max Phase: Preclinical

Molecular Formula: C19H20Cl2N2O4S

Molecular Weight: 443.35

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H20Cl2N2O4S/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:  TXXVMKBMGDYSSR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    8.8281   -3.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2409   -4.2387    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6493   -3.5263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1222   -4.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1210   -5.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8291   -5.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5387   -5.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5359   -4.6519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8273   -4.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9535   -4.6410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6727   -4.2530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3651   -4.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0838   -4.2952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1078   -3.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4072   -3.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6914   -3.4384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4130   -5.8830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6694   -5.5534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1221   -6.1602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5302   -6.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3296   -6.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4992   -4.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3095   -6.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8286   -6.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0160   -6.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6842   -5.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7793   -4.7243    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.4279   -2.2317    0.0000 Cl  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:

   

   ALA4097043

   (3,5-Dichlorophenyl) 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: 443.35

Molecular Weight (Monoisotopic): 442.0521

AlogP: 4.80

#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: 4.77

CX LogD: 4.77

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.44

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