5-Benzyloxy-quinazoline-2,4-diamine

ID: ALA342595

Chembl Id: CHEMBL342595

Cas Number: 123241-95-2

PubChem CID: 11536300

Max Phase: Preclinical

Molecular Formula: C15H14N4O

Molecular Weight: 266.30

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(OCc3ccccc3)cccc2n1

Standard InChI:  InChI=1S/C15H14N4O/c16-14-13-11(18-15(17)19-14)7-4-8-12(13)20-9-10-5-2-1-3-6-10/h1-8H,9H2,(H4,16,17,18,19)

Standard InChI Key:  NHYQPQNHEXBWBH-UHFFFAOYSA-N

Alternative Forms

Associated Targets(Human)

DCPS Tchem Scavenger mRNA-decapping enzyme DcpS (115 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHFR Tclin Dihydrofolate reductase (3072 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

folA Dihydrofolate reductase (1415 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHFR Dihydrofolate reductase (644 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
dengue virus type 2 (2400 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: 266.30Molecular Weight (Monoisotopic): 266.1168AlogP: 2.37#Rotatable Bonds: 3
Polar Surface Area: 87.05Molecular Species: NEUTRALHBA: 5HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 7.61CX LogP: 2.61CX LogD: 2.20
Aromatic Rings: 3Heavy Atoms: 20QED Weighted: 0.76Np Likeness Score: -0.64

References

1. Harris NV, Smith C, Bowden K..  (1990)  Antifolate and antibacterial activities of 5-substituted 2,4-diaminoquinazolines.,  33  (1): [PMID:2404122] [10.1021/jm00163a067]
2. Chao B, Tong XK, Tang W, Li DW, He PL, Garcia JM, Zeng LM, Gao AH, Yang L, Li J, Nan FJ, Jacobs M, Altmeyer R, Zuo JP, Hu YH..  (2012)  Discovery and optimization of 2,4-diaminoquinazoline derivatives as a new class of potent dengue virus inhibitors.,  55  (7): [PMID:22448770] [10.1021/jm2015952]
3. Gopalsamy A, Narayanan A, Liu S, Parikh MD, Kyne RE, Fadeyi O, Tones MA, Cherry JJ, Nabhan JF, LaRosa G, Petersen DN, Menard C, Foley TL, Noell S, Ren Y, Loria PM, Maglich-Goodwin J, Rong H, Jones LH..  (2017)  Design of Potent mRNA Decapping Scavenger Enzyme (DcpS) Inhibitors with Improved Physicochemical Properties To Investigate the Mechanism of Therapeutic Benefit in Spinal Muscular Atrophy (SMA).,  60  (7): [PMID:28257199] [10.1021/acs.jmedchem.7b00124]
4. Gehringer M, Laufer SA..  (2019)  Emerging and Re-Emerging Warheads for Targeted Covalent Inhibitors: Applications in Medicinal Chemistry and Chemical Biology.,  62  (12): [PMID:30565923] [10.1021/acs.jmedchem.8b01153]

Source