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

ID: ALA4534157

PubChem CID: 155546793

Max Phase: Preclinical

Molecular Formula: C20H13Cl2N3O4S2

Molecular Weight: 494.38

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H13Cl2N3O4S2/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:  GMELBBZUKRQOIY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   18.7360  -11.8082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4764  -12.1629    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.4134  -11.3444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5844  -12.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5844  -13.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2897  -13.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2897  -12.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9950  -12.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9995  -13.2948    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7790  -13.5434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2564  -12.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7717  -12.2196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2897  -11.2467    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.8773  -13.7034    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.0397  -14.3220    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8399  -14.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4962  -14.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0735  -12.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2954  -12.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7041  -12.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5205  -12.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9260  -12.1529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5090  -11.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6940  -11.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5820  -10.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5864  -10.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8796   -9.6113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1709  -10.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1735  -10.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8810  -11.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4626   -9.6123    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  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:

   

   ALA4534157

   ---

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: 494.38

Molecular Weight (Monoisotopic): 492.9725

AlogP: 5.67

#Rotatable Bonds: 6

Polar Surface Area: 94.58

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.02

CX Basic pKa: 0.92

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.25

Np Likeness Score: -1.70

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]

2. Fersing C,Boudot C,Castera-Ducros C,Pinault E,Hutter S,Paoli-Lombardo R,Primas N,Pedron J,Seguy L,Bourgeade-Delmas S,Sournia-Saquet A,Stigliani JL,Brossas JY,Paris L,Valentin A,Wyllie S,Fairlamb AH,Boutet-Robinet É,Corvaisier S,Since M,Malzert-Fréon A,Destere A,Mazier D,Rathelot P,Courtioux B,Azas N,Verhaeghe P,Vanelle P.  (2020)  8-Alkynyl-3-nitroimidazopyridines display potent antitrypanosomal activity against both T. b. brucei and cruzi.,  202  [PMID:32652409] [10.1016/j.ejmech.2020.112558]

Source

Source(1):

• Scientific Literature