compound 1u [PMID: 30245402]   Click here for help

GtoPdb Ligand ID: 10258

Antimalarial Ligand
Compound class: Synthetic organic
Comment: Compound 1u is the hit compound identified from a SAR study of peptoid-based histone deacetylase (HDAC) inhibitors for use as antimalarial agents [1].

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 98.74
Molecular weight 451.25
XLogP 4.65
No. Lipinski's rules broken 0
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Canonical SMILES ONC(=O)c1ccc(cc1)CN(C(=O)c1ccc(cc1)C(C)C)CC(=O)NC1CCCCC1
Isomeric SMILES ONC(=O)c1ccc(cc1)CN(C(=O)c1ccc(cc1)C(C)C)CC(=O)NC1CCCCC1
InChI InChI=1S/C26H33N3O4/c1-18(2)20-12-14-22(15-13-20)26(32)29(17-24(30)27-23-6-4-3-5-7-23)16-19-8-10-21(11-9-19)25(31)28-33/h8-15,18,23,33H,3-7,16-17H2,1-2H3,(H,27,30)(H,28,31)
1. Diedrich D, Stenzel K, Hesping E, Antonova-Koch Y, Gebru T, Duffy S, Fisher G, Schöler A, Meister S, Kurz T et al.. (2018)
One-pot, multi-component synthesis and structure-activity relationships of peptoid-based histone deacetylase (HDAC) inhibitors targeting malaria parasites.
Eur J Med Chem, 158: 801-813. [PMID:30245402]
2. Koehne E, Kreidenweiss A, Zoleko Manego R, McCall M, Mombo-Ngoma G, Mackwitz MKW, Hansen FK, Held J. (2019)
Histone deacetylase inhibitors with high in vitro activities against Plasmodium falciparum isolates collected from Gabonese children and adults.
Sci Rep, 9 (1): 17336. [PMID:31758015]