6-chloro-8-(4-chlorophenylthio)-2-(phenylsulfonylmethyl)imidazo[1,2-a]pyridin-3-amine

ID: ALA4555847

PubChem CID: 155556865

Max Phase: Preclinical

Molecular Formula: C20H15Cl2N3O2S2

Molecular Weight: 464.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1c(CS(=O)(=O)c2ccccc2)nc2c(Sc3ccc(Cl)cc3)cc(Cl)cn12

Standard InChI:  InChI=1S/C20H15Cl2N3O2S2/c21-13-6-8-15(9-7-13)28-18-10-14(22)11-25-19(23)17(24-20(18)25)12-29(26,27)16-4-2-1-3-5-16/h1-11H,12,23H2

Standard InChI Key:  YLFUUZHASFMYTD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    8.4303   -3.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1707   -4.2799    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1077   -3.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2787   -4.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2787   -5.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9840   -5.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9840   -4.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6893   -4.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6938   -5.4118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4733   -5.6604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9507   -4.9957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4660   -4.3365    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9840   -3.3637    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5716   -5.8204    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.7678   -4.9912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9897   -4.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3984   -4.9846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2148   -4.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6203   -4.2699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2033   -3.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3883   -3.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763   -2.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2807   -2.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5739   -1.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652   -2.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8678   -2.9584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5753   -3.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1569   -1.7293    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.7301   -6.4362    0.0000 N   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
 11 15  1  0
 15  2  1  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
 10 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4555847

   ---

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: 464.40

Molecular Weight (Monoisotopic): 462.9983

AlogP: 5.35

#Rotatable Bonds: 5

Polar Surface Area: 77.46

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.32

CX LogP: 4.52

CX LogD: 4.49

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.43

Np Likeness Score: -1.57

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