2-(4-(8-Amino-3-oxo-2-phenyl-2,3-dihydro-1,2,4-triazolo-[4,3-a]pyrazin-6-yl)phenoxy)acetonitrile

ID: ALA4578482

PubChem CID: 155564753

Max Phase: Preclinical

Molecular Formula: C19H14N6O2

Molecular Weight: 358.36

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  N#CCOc1ccc(-c2cn3c(=O)n(-c4ccccc4)nc3c(N)n2)cc1

Standard InChI:  InChI=1S/C19H14N6O2/c20-10-11-27-15-8-6-13(7-9-15)16-12-24-18(17(21)22-16)23-25(19(24)26)14-4-2-1-3-5-14/h1-9,12H,11H2,(H2,21,22)

Standard InChI Key:  WWQYFWNNAFDIPN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   31.9475  -27.2273    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.9463  -28.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6544  -28.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6526  -26.8184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3612  -27.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3615  -28.0423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1401  -28.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6211  -27.6326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.1397  -26.9705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4352  -27.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8434  -28.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6598  -28.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0690  -27.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6557  -26.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8407  -26.9279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3929  -29.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.6501  -26.0012    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.2402  -28.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5325  -28.0443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8250  -28.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8239  -29.2697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5362  -29.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2409  -29.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1164  -29.6787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4085  -29.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7010  -29.6794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9968  -30.0872    0.0000 N   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
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  9  5  2  0
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 12 13  2  0
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 14 15  2  0
 15 10  1  0
  8 10  1  0
  7 16  2  0
  4 17  1  0
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 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  2 18  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4578482

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 358.36

Molecular Weight (Monoisotopic): 358.1178

AlogP: 2.03

#Rotatable Bonds: 4

Polar Surface Area: 111.23

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.02

CX LogP: 1.85

CX LogD: 1.70

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.60

Np Likeness Score: -1.54

References

1. Falsini M, Catarzi D, Varano F, Ceni C, Dal Ben D, Marucci G, Buccioni M, Volpini R, Di Cesare Mannelli L, Lucarini E, Ghelardini C, Bartolucci G, Menicatti M, Colotta V..  (2019)  Antioxidant-Conjugated 1,2,4-Triazolo[4,3-a]pyrazin-3-one Derivatives: Highly Potent and Selective Human A_2A Adenosine Receptor Antagonists Possessing Protective Efficacy in Neuropathic Pain.,  62  (18): [PMID:31453698] [10.1021/acs.jmedchem.9b00778]

Source

Source(1):

• Scientific Literature