Optimization of chloronitrobenzamides (CNBs) as therapeutic leads for human African trypanosomiasis (HAT)

Journal of Medicinal Chemistry

Volumn 56, Issue 7, 2013, Pages 2850-2860

  Hwang, Jong Yeon ^a   Smithson, David ^a   Zhu, Fangyi ^a   Holbrook, Gloria ^a   Connelly, Michele C ^a   Kaiser, Marcel ^b,c   Brun, Reto ^b,c   Guy, R Kiplin ^a  

^a ST JUDE CHILDREN S RESEARCH HOSPITAL   (United States)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITRYPANOSOMAL AGENT; CHLORONITROBENZAMIDE DERIVATIVE; EFLORNITHINE; MELARSOPROL; METHYLPIPERAZINE DERIVATIVE; NIFURTIMOX; PENTAMIDINE; PIPERAZINE DERIVATIVE; SURAMIN; UNCLASSIFIED DRUG;

AFRICAN TRYPANOSOMIASIS; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; FEMALE; HUMAN; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; QUANTITATIVE STRUCTURE PROPERTY RELATION; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA BRUCEI; TRYPANOSOMA GAMBIENSE; TRYPANOSOMA RHODESIENSE;

ANIMALS; BENZAMIDES; CELL LINE; DRUG EVALUATION, PRECLINICAL; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMIASIS, AFRICAN;

EID: 84876241768     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301687p     Document Type: Article

References (22)

1. Jacobs, R. T.; Nare, B.; Phillips, M. A. State of the art in African trypanosome drug discovery Curr. Top. Med. Chem. 2011, 11, 1255-1274
2. Welburn, S. C.; Maudlin, I. Priorities for the elimination of sleeping sickness Adv. Parasitol. 2012, 79, 299-337
3. Delespaux, V.; de Koning, H. P. Drugs and drug resistance in African trypanosomiasis Drug Resist. Update 2007, 10, 30-50
4. Rodgers, J. Human African trypanosomiasis, chemotherapy and CNS disease J. Neuroimmunol. 2009, 211, 16-22
5. Priotto, G.; Kasparian, S.; Mutombo, W.; Ngouama, D.; Ghorashian, S.; Arnold, U.; Ghabri, S.; Baudin, E.; Buard, V.; Kazadi-Kyanza, S.; Ilunga, M.; Mutangala, W.; Pohlig, G.; Schmid, C.; Karunakara, U.; Torreele, E.; Kande, V. Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, noninferiority trial Lancet 2009, 374, 56-64
6. Fevre, E. M.; Wissmann, B. V.; Welburn, S. C.; Lutumba, P. The burden of human African trypanosomiasis PLoS Negl. Trop. Dis. 2008, 2, e333
7. Simarro, P. P.; Jannin, J.; Cattand, P. Eliminating human African trypanosomiasis: where do we stand and what comes next? PLoS Med. 2008, 5, e55
8. Kuettel, S.; Zambon, A.; Kaiser, M.; Brun, R.; Scapozza, L.; Perozzo, R. Synthesis and evaluation of antiparasitic activities of new 4-[5-(4- phenoxyphenyl)-2 H -pyrazol-3-yl]morpholine derivatives J. Med. Chem. 2007, 50, 5833-5839
9. Bakunov, S. A.; Bakunova, S. M.; Wenzler, T.; Barszcz, T.; Werbovetz, K. A.; Brun, R.; Tidwell, R. R. Synthesis and antiprotozoal activity of cationic 2-phenylbenzofurans J. Med. Chem. 2008, 51, 6927-6944
10. Bolognesi, M. L.; Lizzi, F.; Perozzo, R.; Brun, R.; Cavalli, A. Synthesis of a small library of 2-phenoxy-1,4-naphthoquinone and 2-phenoxy-1,4- anthraquinone derivatives bearing anti-trypanosomal and anti-leishmanial activity Bioorg. Med. Chem. Lett. 2008, 18, 2272-2276
11. Ismail, M. A.; Arafa, R. K.; Wenzler, T.; Brun, R.; Tanious, F. A.; Wilson, W. D.; Boykin, D. W. Synthesis and antiprotozoal activity of novel bis-benzamidino imidazo[1,2- a ]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2- a ]pyridines Bioorg. Med. Chem. 2008, 16, 683-691
12. Papanastasiou, I.; Tsotinis, A.; Kolocouris, N.; Prathalingam, S. R.; Kelly, J. M. Design, synthesis, and trypanocidal activity of new aminoadamantane derivatives J. Med. Chem. 2008, 51, 1496-1500
13. Weis, R.; Seebacher, W. New bicyclic amines: synthesis and SARs of their action against the causative organisms of malaria and sleeping sickness Curr. Med. Chem. 2009, 16, 1426-1441
14. Hwang, J. Y.; Smithson, D.; Connelly, M.; Maier, J.; Zhu, F.; Guy, K. R. Discovery of halo-nitrobenzamides with potential application against human African trypanosomiasis Bioorg. Med. Chem. Lett. 2010, 20, 149-152
15. Hwang, J. Y.; Attia, R. R.; Carrillo, A. K.; Connelly, M. C.; Guy, R. K. Synthesis and evaluation of methylsulfonylnitrobenzamides (MSNBAs) as inhibitors of the thyroid hormone receptor-coactivator interaction Bioorg. Med. Chem. Lett. 2013, 23, 1891-1895
16. Hwang, J. Y.; Attia, R. R.; Zhu, F.; Yang, L.; Lemoff, A.; Jeffries, C.; Connelly, M. C.; Guy, R. K. Synthesis and evaluation of sulfonylnitrophenylthiazoles (SNPTs) as thyroid hormone receptor-coactivator interaction inhibitors J. Med. Chem. 2012, 55, 2301-2310
17. Hwang, J. Y.; Huang, W.; Arnold, L. A.; Huang, R.; Attia, R. R.; Connelly, M.; Wichterman, J.; Zhu, F.; Augustinaite, I.; Austin, C. P.; Inglese, J.; Johnson, R. L.; Guy, R. K. Methylsulfonylnitrobenzoates, a new class of irreversible inhibitors of the interaction of the thyroid hormone receptor and its obligate coactivators that functionally antagonizes thyroid hormone J. Biol. Chem. 2011, 286, 11895-11908
18. Mackey, Z. B.; Baca, A. M.; Mallari, J. P.; Apsel, B.; Shelat, A.; Hansell, E. J.; Chiang, P. K.; Wolff, B.; Guy, K. R.; Williams, J.; McKerrow, J. H. Discovery of trypanocidal compounds by whole cell HTS of Trypanosoma brucei Chem. Biol. Drug Des. 2006, 67, 355-363
19. Lemoff, A.; Yan, B. Dual detection approach to a more accurate measure of relative purity in high-throughput characterization of compound collections J. Comb. Chem. 2008, 10, 746-751
20. Lindenberg, M.; Kopp, S.; Dressman, J. B. Classification of orally administered drugs on the World Health Organization Model List of Essential Medicines according to the biopharmaceutics classification system Eur. J. Pharm. Biopharm. 2004, 58, 265-278
21. Wu, C. Y.; Benet, L. Z. Predicting drug disposition via application of BCS: transport/absorption/elimination interplay and development of a biopharmaceutics drug disposition classification system Pharm. Res. 2005, 22, 11-23
22. Baltz, T.; Baltz, D.; Giroud, C.; Crockett, J. Cultivation in a semidefined medium of animal infective forms of Trypanosoma brucei, T. equiperdum, T. evansi, T. rhodesiense and T. gambiense EMBO J. 1985, 4, 1273-1277