2-(1,1-Difluoroethyl)-N-(6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

ID: ALA4747214

PubChem CID: 162650133

Max Phase: Preclinical

Molecular Formula: C18H18BrF2N5

Molecular Weight: 422.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(NC2CCc3cc(Br)ccc3C2)n2nc(C(C)(F)F)nc2n1

Standard InChI:  InChI=1S/C18H18BrF2N5/c1-10-7-15(26-17(22-10)24-16(25-26)18(2,20)21)23-14-6-4-11-8-13(19)5-3-12(11)9-14/h3,5,7-8,14,23H,4,6,9H2,1-2H3

Standard InChI Key:  KUSWFJYHVKCDSX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   13.8015   -6.8182    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.8056   -7.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5112   -7.2232    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.7346   -8.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0303   -8.4764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3206   -8.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3110   -7.2589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0194   -6.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7291   -7.2465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5034   -6.9868    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9912   -7.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5147   -8.3092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0098   -6.0249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6163   -8.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5958   -6.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3001   -5.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2946   -4.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5849   -4.4031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8807   -4.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1668   -4.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625   -4.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4680   -5.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1818   -6.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8861   -5.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7528   -4.4239    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.2217   -8.3439    0.0000 C   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
  6 14  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 15 24  1  0
 19 24  2  0
 21 25  1  0
 13 16  1  0
 11  2  1  0
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4747214

   ---

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: 422.28

Molecular Weight (Monoisotopic): 421.0714

AlogP: 4.28

#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: 4.85

CX LogD: 4.85

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.69

Np Likeness Score: -1.53

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]

2. 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