6-(4-Bromophenyl)-8-(1-cyclohexyl-1H-benzo[d]imidazole-6-yl)imidazo[1,2-a]pyrazine

ID: ALA5290943

Max Phase: Preclinical

Molecular Formula: C25H22BrN5

Molecular Weight: 472.39

Names and Identifiers

Canonical SMILES:  Brc1ccc(-c2cn3ccnc3c(-c3ccc4ncn(C5CCCCC5)c4c3)n2)cc1

Standard InChI:  InChI=1S/C25H22BrN5/c26-19-9-6-17(7-10-19)22-15-30-13-12-27-25(30)24(29-22)18-8-11-21-23(14-18)31(16-28-21)20-4-2-1-3-5-20/h6-16,20H,1-5H2

Standard InChI Key:  ZKBXHSGSXIBFCV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 36  0  0  0  0  0  0  0  0999 V2000
   16.0700   -2.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0689   -3.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7769   -4.0474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4866   -3.6379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7751   -2.4100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4809   -2.8183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0874   -2.2732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7564   -1.5279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9454   -1.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1955   -4.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1969   -4.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6071   -4.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8983   -3.6301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6124   -4.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9089   -5.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0836   -6.0628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8951   -6.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2218   -5.3958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5452   -6.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7442   -6.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2022   -7.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4558   -7.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2568   -8.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8041   -7.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3627   -4.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6551   -3.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9475   -4.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9464   -4.8613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6588   -5.2703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3634   -4.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2389   -5.2702    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  1  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
 10 11  2  0
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 14 12  1  0
 12 13  2  0
 13 10  1  0
  4 10  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 16 19  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
  2 25  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5290943

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 472.39

Molecular Weight (Monoisotopic): 471.1059

AlogP: 6.68

#Rotatable Bonds: 3

Polar Surface Area: 48.01

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.03

CX LogP: 5.69

CX LogD: 5.68

Aromatic Rings: 5

Heavy Atoms: 31

QED Weighted: 0.29

Np Likeness Score: -1.23

References

1. Singh I, Luxami V, Paul K..  (2019)  Effective synthesis of benzimidazoles-imidazo[1,2-a]pyrazine conjugates: A comparative study of mono-and bis-benzimidazoles for antitumor activity.,  180  [PMID:31344614] [10.1016/j.ejmech.2019.07.042]

Source

Source(1):

• Scientific Literature