GNF-Pf-3356

ID: ALA579731

Chembl Id: CHEMBL579731

PubChem CID: 5718145

Max Phase: Preclinical

Molecular Formula: C26H27ClN4

Molecular Weight: 430.98

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: GNF-Pf-3356 | GNF-Pf-3356|CHEMBL579731|Probes1_000279|Probes1_000380|Probes2_000225|Probes2_000372|SCHEMBL15165345|BDBM50504518|AKOS001582785|PD169356|N-{2-[(E)-2-(4-chlorophenyl)-1-ethenyl]benzo[g]quinazolin-4-yl}-N-[2-(diethylamino)ethyl]amine

Canonical SMILES:  CCN(CC)CCNc1nc(/C=C/c2ccc(Cl)cc2)nc2cc3ccccc3cc12

Standard InChI:  InChI=1S/C26H27ClN4/c1-3-31(4-2)16-15-28-26-23-17-20-7-5-6-8-21(20)18-24(23)29-25(30-26)14-11-19-9-12-22(27)13-10-19/h5-14,17-18H,3-4,15-16H2,1-2H3,(H,28,29,30)/b14-11+

Standard InChI Key:  MSOORHLGOVMZQM-SDNWHVSQSA-N

Associated Targets(Human)

Huh-7 (12904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FLT3 Tclin Tyrosine-protein kinase receptor FLT3 (13481 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ftsZ Cell division protein ftsZ (97 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ftsZ Cell division protein FtsZ (54 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ftsZ Cell division protein FtsZ (65 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: 430.98Molecular Weight (Monoisotopic): 430.1924AlogP: 6.36#Rotatable Bonds: 8
Polar Surface Area: 41.05Molecular Species: BASEHBA: 4HBD: 1
#RO5 Violations: 1HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: 9.29CX LogP: 6.99CX LogD: 5.10
Aromatic Rings: 4Heavy Atoms: 31QED Weighted: 0.33Np Likeness Score: -1.05

References

1. Plouffe D, Brinker A, McNamara C, Henson K, Kato N, Kuhen K, Nagle A, Adrián F, Matzen JT, Anderson P, Nam TG, Gray NS, Chatterjee A, Janes J, Yan SF, Trager R, Caldwell JS, Schultz PG, Zhou Y, Winzeler EA..  (2008)  In silico activity profiling reveals the mechanism of action of antimalarials discovered in a high-throughput screen.,  105  (26): [PMID:18579783] [10.1073/pnas.0802982105]
2. Keffer JL, Huecas S, Hammill JT, Wipf P, Andreu JM, Bewley CA..  (2013)  Chrysophaentins are competitive inhibitors of FtsZ and inhibit Z-ring formation in live bacteria.,  21  (18): [PMID:23932448] [10.1016/j.bmc.2013.07.033]
3. Nepomuceno GM, Chan KM, Huynh V, Martin KS, Moore JT, O'Brien TE, Pollo LA, Sarabia FJ, Tadeus C, Yao Z, Anderson DE, Ames JB, Shaw JT..  (2015)  Synthesis and Evaluation of Quinazolines as Inhibitors of the Bacterial Cell Division Protein FtsZ.,  (3): [PMID:25815151] [10.1021/ml500497s]
4. Matsui T, Lallo S, Nisa K, Morita H..  (2017)  Filamenting temperature-sensitive mutant Z inhibitors from Glycyrrhiza glabra and their inhibitory mode of action.,  27  (6): [PMID:28196701] [10.1016/j.bmcl.2017.01.095]
5. Zhou D, Springer MZ, Xu D, Liu D, Hudmon A, Macleod KF, Meroueh SO..  (2017)  Small molecules inhibit STAT3 activation, autophagy, and cancer cell anchorage-independent growth.,  25  (12): [PMID:28438385] [10.1016/j.bmc.2017.03.048]
6. Baska F, Sipos A, Őrfi Z, Nemes Z, Dobos J, Szántai-Kis C, Szabó E, Szénási G, Dézsi L, Hamar P, Cserepes MT, Tóvári J, Garamvölgyi R, Krekó M, Őrfi L..  (2019)  Discovery and development of extreme selective inhibitors of the ITD and D835Y mutant FLT3 kinases.,  184  [PMID:31614258] [10.1016/j.ejmech.2019.111710]
7. Hurley KA, Santos TM, Nepomuceno GM, Huynh V, Shaw JT, Weibel DB..  (2016)  Targeting the Bacterial Division Protein FtsZ.,  59  (15): [PMID:26756351] [10.1021/acs.jmedchem.5b01098]
8. Huecas S, Araújo-Bazán L, Ruiz FM, Ruiz-Ávila LB, Martínez RF, Escobar-Peña A, Artola M, Vázquez-Villa H, Martín-Fontecha M, Fernández-Tornero C, López-Rodríguez ML, Andreu JM..  (2021)  Targeting the FtsZ Allosteric Binding Site with a Novel Fluorescence Polarization Screen, Cytological and Structural Approaches for Antibacterial Discovery.,  64  (9.0): [PMID:33908781] [10.1021/acs.jmedchem.0c02207]
9. Buroni S, Makarov V, Scoffone VC, Trespidi G, Riccardi G, Chiarelli LR..  (2020)  The cell division protein FtsZ as a cellular target to hit cystic fibrosis pathogens.,  190  [PMID:32066012] [10.1016/j.ejmech.2020.112132]