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

ID: ALA4761666

PubChem CID: 162660313

Max Phase: Preclinical

Molecular Formula: C18H18ClF2N5

Molecular Weight: 377.83

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H18ClF2N5/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:  IWFHYSLDEVNARR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   15.6917  -10.6689    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.6959  -11.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4015  -11.0739    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.6198  -11.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9113  -12.2876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2058  -11.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2089  -11.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9216  -10.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6270  -11.0681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4023  -10.8203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8808  -11.4837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3948  -12.1385    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9246   -9.8361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4931  -12.2793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5106   -9.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2192   -9.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2223   -8.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5168   -8.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8082   -8.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1028   -8.1850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3942   -8.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3870   -9.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0925   -9.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8010   -9.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6888   -8.1767    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.1039  -12.1960    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:

   

   ALA4761666

   ---

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: 377.83

Molecular Weight (Monoisotopic): 377.1219

AlogP: 4.17

#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: 4.64

CX LogD: 4.64

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.74

Np Likeness Score: -1.65

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