1-((3-(trifluoromethoxy)phenyl)amino)-3-(trifluoromethyl)benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitrile

ID: ALA4514536

PubChem CID: 155539337

Max Phase: Preclinical

Molecular Formula: C20H10F6N4O

Molecular Weight: 436.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(C(F)(F)F)cc(Nc2cccc(OC(F)(F)F)c2)n2c1nc1ccccc12

Standard InChI:  InChI=1S/C20H10F6N4O/c21-19(22,23)14-9-17(28-11-4-3-5-12(8-11)31-20(24,25)26)30-16-7-2-1-6-15(16)29-18(30)13(14)10-27/h1-9,28H

Standard InChI Key:  JHQSWRYUFHWOIN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.3703  -21.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0755  -20.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0755  -20.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703  -19.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703  -22.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3703  -22.8814    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7827  -21.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7815  -22.0693    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4910  -20.8446    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.4880  -21.6597    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6650  -20.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6605  -20.0254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8892  -21.0992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4052  -20.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8842  -19.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5514  -19.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400  -18.9537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2624  -19.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5978  -20.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3714  -18.7954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0796  -18.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860  -18.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4938  -18.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4953  -17.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7832  -17.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783  -17.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2007  -18.8018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9092  -18.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6161  -18.8044    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.9107  -17.5773    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.6135  -17.9782    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 12  4  1  0
 11  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  1  5  1  0
  5  6  3  0
  2  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 11 12  1  0
 12 15  1  0
 14 13  1  0
 13 11  2  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  4 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 23 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4514536

   ---

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: 436.32

Molecular Weight (Monoisotopic): 436.0759

AlogP: 6.02

#Rotatable Bonds: 3

Polar Surface Area: 62.35

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.00

CX LogP: 5.86

CX LogD: 5.86

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.40

Np Likeness Score: -1.63

References

1. Mayoka G, Njoroge M, Okombo J, Gibhard L, Sanches-Vaz M, Fontinha D, Birkholtz LM, Reader J, van der Watt M, Coetzer TL, Lauterbach S, Churchyard A, Bezuidenhout B, Egan TJ, Yeates C, Wittlin S, Prudêncio M, Chibale K..  (2019)  Structure-Activity Relationship Studies and Plasmodium Life Cycle Profiling Identifies Pan-Active N-Aryl-3-trifluoromethyl Pyrido[1,2- a]benzimidazoles Which Are Efficacious in an in Vivo Mouse Model of Malaria.,  62  (2): [PMID:30562027] [10.1021/acs.jmedchem.8b01769]

2. Dziwornu GA, Attram HD, Gachuhi S, Chibale K..  (2020)  Chemotherapy for human schistosomiasis: how far have we come? What's new? Where do we go from here?,  11  (4.0): [PMID:33479649] [10.1039/D0MD00062K]

Source

Source(1):

• Scientific Literature