AN13762   Click here for help

GtoPdb Ligand ID: 10085

Synonyms: AN762
Antimalarial Ligand
Compound class: Synthetic organic
Comment: AN13762 is a preclinical antimalarial candidate optimized from the benzoxaboroles, a novel class of boron-containing compound [2].

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 7
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 105.01
Molecular weight 355.13
XLogP 0.36
No. Lipinski's rules broken 0
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Canonical SMILES O=C(c1cnc(cn1)Oc1ccc2c(c1C)B(O)OC2)N1CC(C1)(C)O
Isomeric SMILES O=C(c1cnc(cn1)Oc1ccc2c(c1C)B(O)OC2)N1CC(C1)(C)O
InChI InChI=1S/C17H18BN3O5/c1-10-13(4-3-11-7-25-18(24)15(10)11)26-14-6-19-12(5-20-14)16(22)21-8-17(2,23)9-21/h3-6,23-24H,7-9H2,1-2H3
1. Sonoiki E, Ng CL, Lee MC, Guo D, Zhang YK, Zhou Y, Alley MR, Ahyong V, Sanz LM, Lafuente-Monasterio MJ et al.. (2017)
A potent antimalarial benzoxaborole targets a Plasmodium falciparum cleavage and polyadenylation specificity factor homologue.
Nat Commun, 8: 14574. [PMID:28262680]
2. Zhang YK, Plattner JJ, Easom EE, Jacobs RT, Guo D, Freund YR, Berry P, Ciaravino V, Erve JCL, Rosenthal PJ et al.. (2017)
Benzoxaborole Antimalarial Agents. Part 5. Lead Optimization of Novel Amide Pyrazinyloxy Benzoxaboroles and Identification of a Preclinical Candidate.
J Med Chem, 60 (13): 5889-5908. [PMID:28635296]
3. Zhang YK, Plattner JJ, Freund YR, Easom EE, Zhou Y, Gut J, Rosenthal PJ, Waterson D, Gamo FJ, Angulo-Barturen I et al.. (2011)
Synthesis and structure-activity relationships of novel benzoxaboroles as a new class of antimalarial agents.
Bioorg Med Chem Lett, 21 (2): 644-51. [PMID:21195617]
4. Zhang YK, Plattner JJ, Freund YR, Easom EE, Zhou Y, Ye L, Zhou H, Waterson D, Gamo FJ, Sanz LM et al.. (2012)
Benzoxaborole antimalarial agents. Part 2: Discovery of fluoro-substituted 7-(2-carboxyethyl)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles.
Bioorg Med Chem Lett, 22 (3): 1299-307. [PMID:22243961]