2-[4-(1H-[1,2,4]-triazol-1-yl)phenyl]-1-(3-chlorobenzyl)-4,6-difluoro-1H-benzo[d]imidazole

ID: ALA550243

PubChem CID: 42645837

Max Phase: Preclinical

Molecular Formula: C22H14ClF2N5

Molecular Weight: 421.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Fc1cc(F)c2nc(-c3ccc(-n4cncn4)cc3)n(Cc3cccc(Cl)c3)c2c1

Standard InChI:  InChI=1S/C22H14ClF2N5/c23-16-3-1-2-14(8-16)11-29-20-10-17(24)9-19(25)21(20)28-22(29)15-4-6-18(7-5-15)30-13-26-12-27-30/h1-10,12-13H,11H2

Standard InChI Key:  BSZIFTAIBXWNHQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    8.8561   -5.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4081   -6.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2151   -6.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7671   -6.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5122   -7.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7052   -7.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1532   -6.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5741   -6.4588    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1110   -4.7910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3246   -3.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3246   -4.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6101   -4.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6101   -3.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1110   -3.4562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8957   -3.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8957   -4.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6261   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6101   -2.4736    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0391   -4.9486    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.8011   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -4.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5636   -4.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1511   -4.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5636   -3.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886   -3.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3261   -4.1236    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8412   -4.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566   -4.5361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0566   -3.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8412   -3.4562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  7  2  1  0
  3  4  1  0
  4  8  1  0
 14 15  1  0
 16  9  1  0
  9 17  1  0
 17 14  2  0
 13 18  1  0
  1  9  1  0
 11 19  1  0
  4  5  2  0
 17 20  1  0
  2  3  2  0
 20 21  2  0
 10 11  2  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 11 12  1  0
 23 24  1  0
 12 16  2  0
 24 25  2  0
 25 20  1  0
  1  2  1  0
 23 26  1  0
 27 28  2  0
 15 13  2  0
 13 10  1  0
 15 16  1  0
  6  7  2  0
 26 27  1  0
 28 29  1  0
 29 30  2  0
 30 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA550243

   1-[(3-Chlorophenyl)methyl]-4,6-difluoro-2-[4-(1,2,4-triazol-1-yl)phenyl]benzimidazole

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 421.84

Molecular Weight (Monoisotopic): 421.0906

AlogP: 5.26

#Rotatable Bonds: 4

Polar Surface Area: 48.53

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.60

CX LogP: 5.52

CX LogD: 5.52

Aromatic Rings: 5

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -2.30

References

1. Jadhav GR, Shaikh MU, Kale RP, Shiradkar MR, Gill CH..  (2009)  SAR study of clubbed [1,2,4]-triazolyl with fluorobenzimidazoles as antimicrobial and antituberculosis agents.,  44  (7): [PMID:19150154] [10.1016/j.ejmech.2008.12.001]

Source

Source(1):

• Scientific Literature