5-(3-Chloro-phenyl)-6-ethyl-pyrimidine-2,4-diamine

ID: ALA278847

Chembl Id: CHEMBL278847

PubChem CID: 10060600

Max Phase: Preclinical

Molecular Formula: C12H13ClN4

Molecular Weight: 248.72

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: TCMDC-137371 | TCMDC-137371 | TCMDC-137371|CHEMBL278847|SCHEMBL11881285|BDBM18784|5-(3-chlorophenyl)-6-ethylpyrimidine-2,4-diamine

Canonical SMILES:  CCc1nc(N)nc(N)c1-c1cccc(Cl)c1

Standard InChI:  InChI=1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-4-3-5-8(13)6-7/h3-6H,2H2,1H3,(H4,14,15,16,17)

Standard InChI Key:  KYIIICAIZHTXJE-UHFFFAOYSA-N

Alternative Forms

Associated Targets(Human)

KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHFR Tclin Dihydrofolate reductase (3072 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLC2A1 Tchem Glucose transporter (14755 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Dihydrofolate reductase (1810 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
folA Dihydrofolate reductase (79 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DFR1 Dihydrofolate reductase (68 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ht1 Hexose transporter 1 (14071 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LmGT2 Glucose transporter (14035 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: 248.72Molecular Weight (Monoisotopic): 248.0829AlogP: 2.52#Rotatable Bonds: 2
Polar Surface Area: 77.82Molecular Species: NEUTRALHBA: 4HBD: 2
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 7.77CX LogP: 2.75CX LogD: 2.24
Aromatic Rings: 2Heavy Atoms: 17QED Weighted: 0.86Np Likeness Score: -1.07

References

1. Tarnchompoo B, Sirichaiwat C, Phupong W, Intaraudom C, Sirawaraporn W, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y..  (2002)  Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum.,  45  (6): [PMID:11881993] [10.1021/jm010131q]
2. McKie JH, Douglas KT, Chan C, Roser SA, Yates R, Read M, Hyde JE, Dascombe MJ, Yuthavong Y, Sirawaraporn W..  (1998)  Rational drug design approach for overcoming drug resistance: application to pyrimethamine resistance in malaria.,  41  (9): [PMID:9554869] [10.1021/jm970845u]
3. Kamchonwongpaisan S, Quarrell R, Charoensetakul N, Ponsinet R, Vilaivan T, Vanichtanankul J, Tarnchompoo B, Sirawaraporn W, Lowe G, Yuthavong Y..  (2004)  Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities.,  47  (3): [PMID:14736247] [10.1021/jm030165t]
4. Parenti MD, Pacchioni S, Ferrari AM, Rastelli G..  (2004)  Three-dimensional quantitative structure-activity relationship analysis of a set of Plasmodium falciparum dihydrofolate reductase inhibitors using a pharmacophore generation approach.,  47  (17): [PMID:15293997] [10.1021/jm040769c]
5. El-Hamamsy MH, Smith AW, Thompson AS, Threadgill MD..  (2007)  Structure-based design, synthesis and preliminary evaluation of selective inhibitors of dihydrofolate reductase from Mycobacterium tuberculosis.,  15  (13): [PMID:17451962] [10.1016/j.bmc.2007.04.011]
6. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]
7. Prado-Prado FJ, García-Mera X, González-Díaz H..  (2010)  Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species.,  18  (6): [PMID:20185316] [10.1016/j.bmc.2010.01.068]
8. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]
9. Tarnchompoo B, Chitnumsub P, Jaruwat A, Shaw PJ, Vanichtanankul J, Poen S, Rattanajak R, Wongsombat C, Tonsomboon A, Decharuangsilp S, Anukunwithaya T, Arwon U, Kamchonwongpaisan S, Yuthavong Y..  (2018)  Hybrid Inhibitors of Malarial Dihydrofolate Reductase with Dual Binding Modes That Can Forestall Resistance.,  (12): [PMID:30613332] [10.1021/acsmedchemlett.8b00389]
10. Saepua S, Sadorn K, Vanichtanankul J, Anukunwithaya T, Rattanajak R, Vitsupakorn D, Kamchonwongpaisan S, Yuthavong Y, Thongpanchang C..  (2019)  6-Hydrophobic aromatic substituent pyrimethamine analogues as potential antimalarials for pyrimethamine-resistant Plasmodium falciparum.,  27  (24): [PMID:31685330] [10.1016/j.bmc.2019.115158]