compound 28 [PMID: 31188540]   Click here for help

GtoPdb Ligand ID: 10617

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Compound 28 is the optimized lead from a novel class of antimalarial compounds based on an aminoacetamide scaffold [3].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 96.12
Molecular weight 469.12
XLogP 2.74
No. Lipinski's rules broken 0
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Canonical SMILES O=C(C(Nc1ccc(c(c1)S(=O)(=O)N1CCOCC1)C)(C)C)Nc1ccc(c(c1)Cl)F
Isomeric SMILES O=C(C(Nc1ccc(c(c1)S(=O)(=O)N1CCOCC1)C)(C)C)Nc1ccc(c(c1)Cl)F
InChI InChI=1S/C21H25ClFN3O4S/c1-14-4-5-16(13-19(14)31(28,29)26-8-10-30-11-9-26)25-21(2,3)20(27)24-15-6-7-18(23)17(22)12-15/h4-7,12-13,25H,8-11H2,1-3H3,(H,24,27)
1. Calderón F, Barros D, Bueno JM, Coterón JM, Fernández E, Gamo FJ, Lavandera JL, León ML, Macdonald SJ, Mallo A et al.. (2011)
An Invitation to Open Innovation in Malaria Drug Discovery: 47 Quality Starting Points from the TCAMS.
ACS Med Chem Lett, 2 (10): 741-6. [PMID:24900261]
2. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S et al.. (2010)
Thousands of chemical starting points for antimalarial lead identification.
Nature, 465 (7296): 305-10. [PMID:20485427]
3. Norcross NR, Wilson C, Baragaña B, Hallyburton I, Osuna-Cabello M, Norval S, Riley J, Fletcher D, Sinden R, Delves M et al.. (2019)
Substituted Aminoacetamides as Novel Leads for Malaria Treatment.
ChemMedChem, 14 (14): 1329-1335. [PMID:31188540]