N-(7,8-Dichloro-4-cyano-3-trifluoromethyl-benzo[4,5]imidazo[1,2-a]pyridin-1-yl)-4-trifluoromethoxy-benzenesulfonamide

ID: ALA4558267

PubChem CID: 155557676

Max Phase: Preclinical

Molecular Formula: C20H8Cl2F6N4O3S

Molecular Weight: 569.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#Cc1c(C(F)(F)F)cc(NS(=O)(=O)c2ccc(OC(F)(F)F)cc2)n2c1nc1cc(Cl)c(Cl)cc12

Standard InChI:  InChI=1S/C20H8Cl2F6N4O3S/c21-13-6-15-16(7-14(13)22)32-17(5-12(19(23,24)25)11(8-29)18(32)30-15)31-36(33,34)10-3-1-9(2-4-10)35-20(26,27)28/h1-7,31H

Standard InChI Key:  GHNGJNBUUWVGJG-UHFFFAOYSA-N

Molfile:  

 
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   30.6075   -6.3889    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.0161   -7.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9013   -9.2491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.6118   -5.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   29.9047   -4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9067   -5.1678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9802   -7.5408    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   26.9357   -6.2106    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.6153   -3.1235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   32.0273   -2.2989    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4558267

   ---

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: 569.27

Molecular Weight (Monoisotopic): 567.9598

AlogP: 6.38

#Rotatable Bonds: 4

Polar Surface Area: 96.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.93

CX Basic pKa: 3.75

CX LogP: 6.11

CX LogD: 5.64

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.29

Np Likeness Score: -1.66

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]

Source

Source(1):

• Scientific Literature