5-(4-bromobenzyl)-6-oxo-2-phenyl-1,6-dihydropyridine-3-carbonitrile

ID: ALA2069992

PubChem CID: 70693053

Max Phase: Preclinical

Molecular Formula: C19H13BrN2O

Molecular Weight: 365.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cc(Cc2ccc(Br)cc2)c(=O)[nH]c1-c1ccccc1

Standard InChI:  InChI=1S/C19H13BrN2O/c20-17-8-6-13(7-9-17)10-15-11-16(12-21)18(22-19(15)23)14-4-2-1-3-5-14/h1-9,11H,10H2,(H,22,23)

Standard InChI Key:  QXQUTJCZHVKUOG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -4.0681  -15.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0693  -16.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3544  -16.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6380  -16.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409  -15.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3562  -14.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9279  -14.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2119  -15.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2122  -16.0219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4970  -16.4317    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169  -16.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111  -15.1872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5046  -14.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9260  -16.4355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335  -16.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9217  -14.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6331  -14.3540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9348  -17.2511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6505  -17.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3638  -17.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570  -16.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407  -16.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7840  -16.4476    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
 13  8  2  0
  1  2  2  0
  9 14  2  0
  5  7  1  0
 11 15  1  0
  3  4  2  0
  7  8  1  0
 16 17  3  0
 12 16  1  0
 15 18  2  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  2  0
  9 10  1  0
 20 21  1  0
  2  3  1  0
 21 22  2  0
 22 15  1  0
 10 11  1  0
  2 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2069992

   5-[(4-bromophenyl)methyl]-6-oxo-2-phenyl-1H-pyridine-3-carbonitrile

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: 365.23

Molecular Weight (Monoisotopic): 364.0211

AlogP: 4.27

#Rotatable Bonds: 3

Polar Surface Area: 56.65

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.31

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -0.73

References

1. Ravinder M, Mahendar B, Mattapally S, Hamsini KV, Reddy TN, Rohit C, Srinivas K, Banerjee SK, Rao VJ..  (2012)  Synthesis and evaluation of novel 2-pyridone derivatives as inhibitors of phosphodiesterase3 (PDE3): a target for heart failure and platelet aggregation.,  22  (18): [PMID:22897945] [10.1016/j.bmcl.2012.05.019]

Source

Source(1):

• Scientific Literature