N-(3-cyano-1-(4-bromobenzyl)-1H-indol-5-yl]-6-oxo-1,6-dihydropyrimidine-4-carboxamide

ID: ALA5208786

PubChem CID: 156780193

Max Phase: Preclinical

Molecular Formula: C21H14BrN5O2

Molecular Weight: 448.28

Names and Identifiers

Canonical SMILES:  N#Cc1cn(Cc2ccc(Br)cc2)c2ccc(NC(=O)c3cc(=O)[nH]cn3)cc12

Standard InChI:  InChI=1S/C21H14BrN5O2/c22-15-3-1-13(2-4-15)10-27-11-14(9-23)17-7-16(5-6-19(17)27)26-21(29)18-8-20(28)25-12-24-18/h1-8,11-12H,10H2,(H,26,29)(H,24,25,28)

Standard InChI Key:  FZGSOLJGDAITGB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.0178    0.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3033    0.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085    0.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4085   -0.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3014   -0.9290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0178   -0.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915   -0.7631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -0.0955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2127    0.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4263    1.3552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6398    2.1522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4050   -1.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021   -1.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858   -1.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803   -1.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7939   -2.2013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2144   -2.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4166   -2.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5910   -2.4149    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7325    0.7201    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4472    0.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8764    0.3075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5910    0.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5910    1.5453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8764    1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617    1.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8764    2.7831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4472   -0.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  4  7  1  0
  7  8  1  0
  9  8  2  0
  3  9  1  0
 10  9  1  0
 10 11  3  0
  7 12  1  0
 12 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 13 18  1  0
 16 19  1  0
  1 20  1  0
 20 21  1  0
 21 22  1  0
 23 22  1  0
 24 23  2  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
 22 27  2  0
 26 28  2  0
 21 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5208786

   ---

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: 448.28

Molecular Weight (Monoisotopic): 447.0331

AlogP: 3.66

#Rotatable Bonds: 4

Polar Surface Area: 103.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.36

CX Basic pKa: ┄

CX LogP: 3.18

CX LogD: 3.14

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -1.76

References

1. Zhang B, Duan Y, Yang Y, Mao Q, Lin F, Gao J, Dai X, Zhang P, Li Q, Li J, Dai R, Wang S..  (2022)  Design, synthesis, and biological evaluation of N-(3-cyano-1H-indol-5/6-yl)-6-oxo-1,6-dihydropyrimidine-4-carboxamides and 5-(6-oxo-1,6-dihydropyrimidin-2-yl)-1H-indole-3-carbonitriles as novel xanthine oxidase inhibitors.,  227  [PMID:34688012] [10.1016/j.ejmech.2021.113928]

Source

Source(1):

• Scientific Literature