4-((1-(2-chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl)methyl)morpholine

ID: ALA2313234

PubChem CID: 71153436

Max Phase: Preclinical

Molecular Formula: C21H20ClN5O

Molecular Weight: 393.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nc2ccc(CN3CCOCC3)cc2n2c(-c3ccccc3Cl)nnc12

Standard InChI:  InChI=1S/C21H20ClN5O/c1-14-20-24-25-21(16-4-2-3-5-17(16)22)27(20)19-12-15(6-7-18(19)23-14)13-26-8-10-28-11-9-26/h2-7,12H,8-11,13H2,1H3

Standard InChI Key:  LZRGPVBUCASWQB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   21.6530   -3.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3611   -4.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0707   -3.9021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0679   -3.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6541   -3.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3584   -2.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9440   -1.8660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9461   -2.6831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6483   -1.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3569   -1.8628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9637   -1.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6300   -0.5684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8171   -0.6551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2348   -1.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7626   -1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0153   -2.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8141   -2.4290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3609   -1.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1034   -1.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3053   -0.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0495   -0.0992    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   23.7791   -4.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4861   -3.8998    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.1928   -4.3129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8978   -3.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9007   -3.0892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1925   -2.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4814   -3.0874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  6  2  0
  5  6  1  0
  5  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  2  0
  7 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 11 15  1  0
 20 21  1  0
  3 22  1  0
 22 23  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2313234

   4-[[1-(2-Chlorophenyl)-4-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-8-yl]methyl]morpholine

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: 393.88

Molecular Weight (Monoisotopic): 393.1356

AlogP: 3.74

#Rotatable Bonds: 3

Polar Surface Area: 55.55

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.83

CX LogP: 2.47

CX LogD: 2.37

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: -1.93

References

1. Andrés JI, Buijnsters P, De Angelis M, Langlois X, Rombouts F, Trabanco AA, Vanhoof G..  (2013)  Discovery of a new series of [1,2,4]triazolo[4,3-a]quinoxalines as dual phosphodiesterase 2/phosphodiesterase 10 (PDE2/PDE10) inhibitors.,  23  (3): [PMID:23260348] [10.1016/j.bmcl.2012.11.077]

2. Gomez L, Breitenbucher JG..  (2013)  PDE2 inhibition: potential for the treatment of cognitive disorders.,  23  (24): [PMID:24189054] [10.1016/j.bmcl.2013.10.014]

3. Buijnsters P, De Angelis M, Langlois X, Rombouts FJ, Sanderson W, Tresadern G, Ritchie A, Trabanco AA, VanHoof G, Roosbroeck YV, Andrés JI..  (2014)  Structure-Based Design of a Potent, Selective, and Brain Penetrating PDE2 Inhibitor with Demonstrated Target Engagement.,  5  (9): [PMID:25221665] [10.1021/ml500262u]

Source

Source(1):

• Scientific Literature