(5-Methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)(4-trifluoromethylphenyl)amine

ID: ALA492529

Cas Number: 898743-92-5

PubChem CID: 25263414

Max Phase: Preclinical

Molecular Formula: C13H10F3N5

Molecular Weight: 293.25

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Synonyms: DSM-74 | DSM74|DSM-74|898743-92-5|A94AKH2DCP|5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine|UNII-A94AKH2DCP|5-methyl-N-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine|5-Methyl-N-(4-(trifluoromethyl)phenyl)(1,2,4)triazolo(1,5-a)pyrimidin-7-amine|(1,2,4)Triazolo(1,5-a)pyrimidin-7-amine, 5-methyl-N-(4-(trifluoromethyl)phenyl)-|CHEMBL492529|SCHEMBL4099123|BDBM28817|LRHHXKBKRNNFRV-UHFFFAOYSA-N|AKOS040746782|DB08008|triazolopyrimidine-based compound, Show More

Canonical SMILES:  Cc1cc(Nc2ccc(C(F)(F)F)cc2)n2ncnc2n1

Standard InChI:  InChI=1S/C13H10F3N5/c1-8-6-11(21-12(19-8)17-7-18-21)20-10-4-2-9(3-5-10)13(14,15)16/h2-7,20H,1H3

Standard InChI Key:  LRHHXKBKRNNFRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.4904   -0.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9386   -0.2480    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6530    0.9895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -1.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377    0.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4904   -1.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4377    2.0694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9386    2.2270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9193   -1.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048   -1.4855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2048   -0.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9386    0.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241    0.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241    1.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4904    2.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6530    1.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9226    1.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6338   -2.3105    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3318   -1.1835    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.5068   -2.6125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  2  0
  1  3  1  0
  3  2  1  0
 13  2  1  0
  3  5  2  0
  4  6  1  0
 13  4  1  0
 17  4  1  0
  5  7  1  0
 18  6  2  0
  7 11  2  0
 18  8  1  0
 17  8  2  0
 17  9  1  0
 15  9  2  0
 10 20  1  0
 10 19  1  0
 10 11  1  0
 10 21  1  0
 12 11  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
M  END

Associated Targets(Human)

DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Liver microsomes (16955 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (7708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Plasmodium berghei (192651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
dhod Dihydroorotate dehydrogenase (710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dhodh Dihydroorotate dehydrogenase (165 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dhodh Dihydroorotate dehydrogenase (104 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 293.25Molecular Weight (Monoisotopic): 293.0888AlogP: 3.20#Rotatable Bonds: 2
Polar Surface Area: 55.11Molecular Species: NEUTRALHBA: 5HBD: 1
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 2.75CX LogD: 2.75
Aromatic Rings: 3Heavy Atoms: 21QED Weighted: 0.79Np Likeness Score: -2.42

References

1. Gujjar R, Marwaha A, El Mazouni F, White J, White KL, Creason S, Shackleford DM, Baldwin J, Charman WN, Buckner FS, Charman S, Rathod PK, Phillips MA..  (2009)  Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.,  52  (7): [PMID:19296651] [10.1021/jm801343r]
2. Gujjar R, El Mazouni F, White KL, White J, Creason S, Shackleford DM, Deng X, Charman WN, Bathurst I, Burrows J, Floyd DM, Matthews D, Buckner FS, Charman SA, Phillips MA, Rathod PK..  (2011)  Lead optimization of aryl and aralkyl amine-based triazolopyrimidine inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with antimalarial activity in mice.,  54  (11): [PMID:21517059] [10.1021/jm200265b]
3. Deng X, Kokkonda S, El Mazouni F, White J, Burrows JN, Kaminsky W, Charman SA, Matthews D, Rathod PK, Phillips MA..  (2014)  Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.,  57  (12): [PMID:24801997] [10.1021/jm500481t]
4. Singh A, Maqbool M, Mobashir M, Hoda N..  (2017)  Dihydroorotate dehydrogenase: A drug target for the development of antimalarials.,  125  [PMID:27721149] [10.1016/j.ejmech.2016.09.085]
5. Boschi D, Pippione AC, Sainas S, Lolli ML..  (2019)  Dihydroorotate dehydrogenase inhibitors in anti-infective drug research.,  183  [PMID:31557612] [10.1016/j.ejmech.2019.111681]

Source