8-benzoylamino-2-phenylimidazo[1,2-a]pyrazine

ID: ALA4092103

PubChem CID: 137656020

Max Phase: Preclinical

Molecular Formula: C19H14N4O

Molecular Weight: 314.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1nccn2cc(-c3ccccc3)nc12)c1ccccc1

Standard InChI:  InChI=1S/C19H14N4O/c24-19(15-9-5-2-6-10-15)22-17-18-21-16(13-23(18)12-11-20-17)14-7-3-1-4-8-14/h1-13H,(H,20,22,24)

Standard InChI Key:  ZBZLIMXLZLGHSQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    2.2686  -17.0124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2674  -17.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9755  -18.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9737  -16.6035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6823  -17.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6825  -17.8320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655  -18.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492  -17.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4651  -16.7543    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9712  -15.7863    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7632  -17.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1714  -18.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9878  -18.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3970  -17.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9838  -16.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1687  -16.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2623  -15.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2599  -14.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5558  -15.7906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9662  -14.1531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9641  -13.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546  -12.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5458  -13.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514  -14.1596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  2  0
  4 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 11  1  0
 10 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4092103

   ---

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: 314.35

Molecular Weight (Monoisotopic): 314.1168

AlogP: 3.65

#Rotatable Bonds: 3

Polar Surface Area: 59.29

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.70

CX LogP: 3.26

CX LogD: 3.26

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -1.63

References

1. Poli D, Falsini M, Varano F, Betti M, Varani K, Vincenzi F, Pugliese AM, Pedata F, Dal Ben D, Thomas A, Palchetti I, Bettazzi F, Catarzi D, Colotta V..  (2017)  Imidazo[1,2-a]pyrazin-8-amine core for the design of new adenosine receptor antagonists: Structural exploration to target the A3 and A2A subtypes.,  125  [PMID:27721147] [10.1016/j.ejmech.2016.09.076]

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