8-(4-Bromophenylthio)-6-chloro-3-nitro-2-(phenylsulfonylmethyl)imidazo[1,2-a]pyridine

ID: ALA4450630

PubChem CID: 155521391

Max Phase: Preclinical

Molecular Formula: C20H13BrClN3O4S2

Molecular Weight: 538.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1c(CS(=O)(=O)c2ccccc2)nc2c(Sc3ccc(Br)cc3)cc(Cl)cn12

Standard InChI:  InChI=1S/C20H13BrClN3O4S2/c21-13-6-8-15(9-7-13)30-18-10-14(22)11-24-19(18)23-17(20(24)25(26)27)12-31(28,29)16-4-2-1-3-5-16/h1-11H,12H2

Standard InChI Key:  ISPROKRBNAORAW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    8.9999  -11.2469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7403  -11.6016    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6772  -10.7831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483  -11.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8483  -12.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5536  -13.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5536  -11.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2588  -11.9153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2634  -12.7335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0429  -12.9821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5202  -12.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0356  -11.6583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5536  -10.6854    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1412  -13.1421    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.3035  -13.7607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1038  -13.9262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7601  -14.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3374  -12.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5592  -11.5984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9679  -12.3063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7844  -12.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1898  -11.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7729  -10.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9579  -10.8915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8459  -10.2768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8503   -9.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1434   -9.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4347   -9.4587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4374  -10.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1448  -10.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7265   -9.0510    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  1  0
  4  7  2  0
  5  6  2  0
  6  9  1  0
  8  7  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  2  0
  7 13  1  0
  5 14  1  0
 15 16  2  0
 15 17  1  0
 10 15  1  0
 11 18  1  0
 18  2  1  0
  2 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
 13 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4450630

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 538.83

Molecular Weight (Monoisotopic): 536.9219

AlogP: 5.78

#Rotatable Bonds: 6

Polar Surface Area: 94.58

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.02

CX Basic pKa: 0.92

CX LogP: 5.45

CX LogD: 5.45

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.23

Np Likeness Score: -1.74

References

1. Fersing C, Basmaciyan L, Boudot C, Pedron J, Hutter S, Cohen A, Castera-Ducros C, Primas N, Laget M, Casanova M, Bourgeade-Delmas S, Piednoel M, Sournia-Saquet A, Belle Mbou V, Courtioux B, Boutet-Robinet É, Since M, Milne R, Wyllie S, Fairlamb AH, Valentin A, Rathelot P, Verhaeghe P, Vanelle P, Azas N..  (2019)  Nongenotoxic 3-Nitroimidazo[1,2-a]pyridines Are NTR1 Substrates That Display Potent in Vitro Antileishmanial Activity.,  10  (1): [PMID:30655943] [10.1021/acsmedchemlett.8b00347]

Source

Source(1):

• Scientific Literature