2-(1,1-difluoroethyl)-N-[3-fluoro-4-(trifluoromethyl)phenyl]-5-methyl [1,2,4]triazolo[1,5-a]pyrimidin-7-amine

ID: ALA3289670

PubChem CID: 51347544

Max Phase: Preclinical

Molecular Formula: C15H11F6N5

Molecular Weight: 375.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Nc2ccc(C(F)(F)F)c(F)c2)n2nc(C(C)(F)F)nc2n1

Standard InChI:  InChI=1S/C15H11F6N5/c1-7-5-11(26-13(22-7)24-12(25-26)14(2,17)18)23-8-3-4-9(10(16)6-8)15(19,20)21/h3-6,23H,1-2H3

Standard InChI Key:  HOTDSHUZUQSKJD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.3383   -1.3500    0.0000 C   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
    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
    0.0031    3.0008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092    5.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6108    5.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9072    5.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9020    3.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9392    3.1369    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2096    5.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2145    7.1864    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2465    5.3825    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2511    6.5823    0.0000 F   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
   -2.7248    1.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6065    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -1.2135    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 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1047    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7044   -1.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7054    1.0388    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3047   -0.0006    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12  6  1  0
  9 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 17  1  0
 21 22  1  0
 22  2  2  0
 19 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3289670

   2-(1,1-difluoroethyl)-N-[3-fluoro-4-(trifluoromethyl)phenyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-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: 375.28

Molecular Weight (Monoisotopic): 375.0919

AlogP: 4.45

#Rotatable Bonds: 3

Polar Surface Area: 55.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.33

CX LogD: 4.33

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -1.93

References

1. Deng X, Kokkonda S, El Mazouni F, White J, Burrows JN, Kaminsky W, Charman SA, Matthews D, Rathod PK, Phillips MA..  (2014)  Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.,  57  (12): [PMID:24801997] [10.1021/jm500481t]

2.  (2016)  Antimalarial agents that are inhibitors of dihydroorotate dehydrogenase, 

Source

Source(2):

• Scientific Literature
• BindingDB Database