(S)-N-(7-Chloro-1,2,3,4-tetrahydronaphthalen-2-yl)-2-(1,1-difluoroethyl)-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

ID: ALA4751920

PubChem CID: 162653432

Max Phase: Preclinical

Molecular Formula: C18H18ClF2N5

Molecular Weight: 377.83

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1cc(N[C@H]2CCc3ccc(Cl)cc3C2)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)23-14-6-4-11-3-5-13(19)8-12(11)9-14/h3,5,7-8,14,23H,4,6,9H2,1-2H3/t14-/m0/s1

Standard InChI Key:  MIVYUYYPBSQCPE-AWEZNQCLSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   16.6936  -11.8168    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9808  -11.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9798  -12.2278    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.8835  -11.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1674  -12.2148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4555  -11.7948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4598  -10.9696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1761  -10.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8921  -10.9801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6754  -10.7311    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1577  -11.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6658  -12.0666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.1846   -9.7390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7394  -12.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7565   -9.7285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4728   -9.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4771   -8.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7652   -8.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0491   -8.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3372   -8.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6168   -8.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6125   -9.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3244   -9.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0447   -9.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8963   -9.7073    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.3994  -10.6935    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
 11  2  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
 22 25  1  0
 16 13  1  6
  2 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4751920

   ---

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: -1.61

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