3-(2-amino-6-phenylpyrimidin-4-yl)phenyl 4-methylpiperazine-1-carboxylate

ID: ALA3753390

PubChem CID: 127037154

Max Phase: Preclinical

Molecular Formula: C22H23N5O2

Molecular Weight: 389.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(C(=O)Oc2cccc(-c3cc(-c4ccccc4)nc(N)n3)c2)CC1

Standard InChI:  InChI=1S/C22H23N5O2/c1-26-10-12-27(13-11-26)22(28)29-18-9-5-8-17(14-18)20-15-19(24-21(23)25-20)16-6-3-2-4-7-16/h2-9,14-15H,10-13H2,1H3,(H2,23,24,25)

Standard InChI Key:  MBMNYBUCPCOZEE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8934   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -6.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -5.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4915   -3.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1925   -3.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969   -9.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8945   -8.2599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1924   -7.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4926   -8.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4949   -9.7559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1971  -10.5079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7958  -10.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0950   -9.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3940  -10.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3939  -12.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0949  -12.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7959  -12.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586  -10.3616    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383    1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  2  0
  7  9  1  0
  1  7  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 10 15  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 22 27  2  0
 20 22  1  0
 16 28  1  0
 12 18  1  0
  9 10  1  0
  4 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3753390

   ---

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: 389.46

Molecular Weight (Monoisotopic): 389.1852

AlogP: 3.14

#Rotatable Bonds: 3

Polar Surface Area: 84.58

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.84

CX LogP: 3.53

CX LogD: 3.43

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.74

Np Likeness Score: -1.02

References

1. Robinson SJ, Petzer JP, Rousseau AL, Terre'Blanche G, Petzer A, Lourens AC..  (2016)  Carbamate substituted 2-amino-4,6-diphenylpyrimidines as adenosine receptor antagonists.,  26  (3): [PMID:26776359] [10.1016/j.bmcl.2016.01.004]

2. Saini A, Patel R, Gaba S, Singh G, Gupta GD, Monga V..  (2022)  Adenosine receptor antagonists: Recent advances and therapeutic perspective.,  227  [PMID:34695776] [10.1016/j.ejmech.2021.113907]

Source

Source(1):

• Scientific Literature