N-(4-Chlorophenyl)-2-(1,1-difluoroethyl)-5-methyl[1,2,4]triazolo-[1,5-a]pyrimidin-7-amine

ID: ALA1956283

Chembl Id: CHEMBL1956283

PubChem CID: 51347101

Max Phase: Preclinical

Molecular Formula: C14H12ClF2N5

Molecular Weight: 323.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(Nc2ccc(Cl)cc2)n2nc(C(C)(F)F)nc2n1

Standard InChI:  InChI=1S/C14H12ClF2N5/c1-8-7-11(19-10-5-3-9(15)4-6-10)22-13(18-8)20-12(21-22)14(2,16)17/h3-7,19H,1-2H3

Standard InChI Key:  RIOPTIZLYYUGNM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1956283

   N-(4-chlorophenyl)-2-(1,1-difluoroethyl)-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: 323.73

Molecular Weight (Monoisotopic): 323.0749

AlogP: 3.94

#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: 3.87

CX LogD: 3.87

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: -2.18

References

1. Coteron JM, Marco M, Esquivias J, Deng X, White KL, White J, Koltun M, El Mazouni F, Kokkonda S, Katneni K, Bhamidipati R, Shackleford DM, Angulo-Barturen I, Ferrer SB, Jiménez-Díaz MB, Gamo FJ, Goldsmith EJ, Charman WN, Bathurst I, Floyd D, Matthews D, Burrows JN, Rathod PK, Charman SA, Phillips MA..  (2011)  Structure-guided lead optimization of triazolopyrimidine-ring substituents identifies potent Plasmodium falciparum dihydroorotate dehydrogenase inhibitors with clinical candidate potential.,  54  (15): [PMID:21696174] [10.1021/jm200592f]

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

Source

Source(2):

• Scientific Literature
• BindingDB Database