N-(5,6-Difluoro-2,3-dihydro-1H-inden-2-yl)-2-(1,1-difluoroethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

ID: ALA4794107

PubChem CID: 162673541

Max Phase: Preclinical

Molecular Formula: C17H15F4N5

Molecular Weight: 365.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(NC2Cc3cc(F)c(F)cc3C2)n2nc(C(C)(F)F)nc2n1

Standard InChI:  InChI=1S/C17H15F4N5/c1-8-3-14(26-16(22-8)24-15(25-26)17(2,20)21)23-11-4-9-6-12(18)13(19)7-10(9)5-11/h3,6-7,11,23H,4-5H2,1-2H3

Standard InChI Key:  SITNTKTWRALOFE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   12.6252   -9.4060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9194   -8.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9185   -9.8129    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8475   -9.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1384   -9.8171    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4293   -9.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4293   -8.5913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1384   -8.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8475   -8.5913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6248   -8.3408    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1049   -8.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6248   -9.6632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1384   -7.3655    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6821   -7.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4293   -6.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3453   -6.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5469   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1383   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3211   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9126   -5.9758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3211   -6.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1383   -6.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7244   -9.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3307   -8.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9123   -4.5591    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.0954   -5.9758    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  4  9  1  0
 10 11  2  0
 11 12  1  0
  9 10  1  0
  4 12  2  0
  8 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 14 22  1  0
 17 22  2  0
 13 15  1  0
  6 23  1  0
 11  2  1  0
  2 24  1  0
 19 25  1  0
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4794107

   ---

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: 365.33

Molecular Weight (Monoisotopic): 365.1264

AlogP: 3.40

#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: 3.95

CX LogD: 3.95

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -1.60

References

1. Kokkonda S,Deng X,White KL,Coteron JM,Marco M,de Las Heras L,White J,El Mazouni F,Tomchick DR,Manjalanagara K,Rudra KR,Chen G,Morizzi J,Ryan E,Kaminsky W,Leroy D,Martínez-Martínez MS,Jimenez-Diaz MB,Bazaga SF,Angulo-Barturen I,Waterson D,Burrows JN,Matthews D,Charman SA,Phillips MA,Rathod PK.  (2016)  Tetrahydro-2-naphthyl and 2-Indanyl Triazolopyrimidines Targeting Plasmodium falciparum Dihydroorotate Dehydrogenase Display Potent and Selective Antimalarial Activity.,  59  (11.0): [PMID:27127993] [10.1021/acs.jmedchem.6b00275]

Source

Source(1):

• Scientific Literature