2-Butyl-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3,5-dihydro-imidazo[4,5-c]pyridin-4-one

ID: ALA429008

PubChem CID: 10025443

Max Phase: Preclinical

Molecular Formula: C24H23N7O

Molecular Weight: 425.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1nc2ccnc(O)c2n1Cc1ccc(-c2ccccc2-c2nn[nH]n2)cc1

Standard InChI:  InChI=1S/C24H23N7O/c1-2-3-8-21-26-20-13-14-25-24(32)22(20)31(21)15-16-9-11-17(12-10-16)18-6-4-5-7-19(18)23-27-29-30-28-23/h4-7,9-14H,2-3,8,15H2,1H3,(H,25,32)(H,27,28,29,30)

Standard InChI Key:  XUZIAARJXWYAQV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   -1.3875    1.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    1.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875    2.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458    1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2250   -1.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7708   -0.4917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2083   -0.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1458   -0.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8083   -1.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7583   -1.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2000   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    2.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167    1.3875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2167    1.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3000    0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5458   -0.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9125    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458    1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    0.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4500   -0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8583   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6458    2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2458    2.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -2.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3875   -2.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5458    2.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  5  2  0
  5  1  1  0
  6 12  1  0
  7  8  2  0
  8  6  1  0
  9 11  1  0
 10  2  1  0
 11  6  2  0
 12 13  2  0
 13 18  1  0
 14  3  1  0
 15 10  2  0
 16  1  1  0
 17 15  1  0
 18 20  2  0
 19 10  1  0
 20 25  1  0
 21 24  2  0
 22 16  1  0
 23  5  1  0
 24 22  1  0
 25 22  2  0
 26 12  1  0
 27 13  1  0
 28 23  1  0
 29 28  1  0
 30 27  2  0
 31 30  1  0
 32 29  1  0
  3  4  1  0
 21 18  1  0
 17 14  2  0
 26 31  2  0
  7  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA429008

   2-butyl-4,5-dihydro-4-oxo-3-[2'-(tetrazol-5-yl)biphenyl-4-ylmethyl]-3H-imidazo[4,5-c]pyridine

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: 425.50

Molecular Weight (Monoisotopic): 425.1964

AlogP: 4.37

#Rotatable Bonds: 7

Polar Surface Area: 105.40

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.85

CX Basic pKa: 4.18

CX LogP: 5.60

CX LogD: 4.45

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -1.06

References

1. Gibson K, Wood R, Oldham A, Major J.  (1993)  The synthesis of heterosubstituted benzimidazole derivatives with potent angiotensin II antagonist activity,  3  (6): [10.1016/S0960-894X(00)80279-6]

2. Mederski WW, Dorsch D, Bokel HH, Beier N, Lues I, Schelling P..  (1994)  Non-peptide angiotensin II receptor antagonists: synthesis and biological activity of a series of novel 4,5-dihydro-4-oxo-3H-imidazo[4,5-c]pyridine derivatives.,  37  (11): [PMID:8201597] [10.1021/jm00037a014]

3. Sharma MC, Kohli DV.  (2013)  A comprehensive structureactivity analysis 2,3,5-trisubstituted 4,5-dihydro-4-oxo-3H-imidazo [4,5-c] pyridine derivatives as angiotensin II receptor antagonists: using 2D- and 3D-QSAR approach,  22  (2): [10.1007/s00044-012-0040-z]

Source

Source(1):

• Scientific Literature