2-Trifluoromethyl-8-(2-methoxybenzyl)-4-(Nmethylamino)pyrazolo[1,5-a]-1,3,5-triazine

ID: ALA516795

PubChem CID: 24829305

Max Phase: Preclinical

Molecular Formula: C15H14F3N5O

Molecular Weight: 337.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc(C(F)(F)F)nc2c(Cc3ccccc3OC)cnn12

Standard InChI:  InChI=1S/C15H14F3N5O/c1-19-14-22-13(15(16,17)18)21-12-10(8-20-23(12)14)7-9-5-3-4-6-11(9)24-2/h3-6,8H,7H2,1-2H3,(H,19,21,22)

Standard InChI Key:  LTVJIZBAUKWGLE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    9.2511   -2.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2511   -2.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5367   -3.2479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5367   -1.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8222   -2.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8222   -2.8354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0376   -3.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5526   -2.4229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0376   -1.7554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5367   -0.7729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2511   -0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9656   -3.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7826   -3.8749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9757   -4.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6801   -3.6604    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3781   -2.5334    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.5531   -3.9623    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.7207   -4.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137   -5.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3617   -4.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -3.6049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4236   -3.4334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2728   -5.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0178   -6.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
  2  3  2  0
  7 13  1  0
  3  6  1  0
 13 14  1  0
  1  2  1  0
 12 15  1  0
  5  4  1  0
 12 16  1  0
  6  7  2  0
 12 17  1  0
  7  8  1  0
 14 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  2  0
 20 21  1  0
  4 10  1  0
 21 22  2  0
 22 14  1  0
  5  6  1  0
 18 23  1  0
 10 11  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA516795

   8-[(2-methoxyphenyl)methyl]-N-methyl-2-(trifluoromethyl)pyrazolo[1,5-a][1,3,5]triazin-4-amine

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: 337.31

Molecular Weight (Monoisotopic): 337.1150

AlogP: 2.78

#Rotatable Bonds: 4

Polar Surface Area: 64.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.72

CX LogP: 3.80

CX LogD: 3.80

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: -1.21

References

1. Raboisson P, Schultz D, Muller C, Reimund JM, Pinna G, Mathieu R, Bernard P, Do QT, Desjarlais RL, Justiano H, Lugnier C, Bourguignon JJ..  (2008)  Cyclic nucleotide phosphodiesterase type 4 inhibitors: evaluation of pyrazolo[1,5-a]-1,3,5-triazine ring system as an adenine bioisostere.,  43  (4): [PMID:17640774] [10.1016/j.ejmech.2007.05.016]

2. Kodimuthali A, Jabaris SS, Pal M..  (2008)  Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease.,  51  (18): [PMID:18686943] [10.1021/jm800582j]

Source

Source(1):

• Scientific Literature