Facile Synthesis and Preliminary Structure-Activity Analysis of New Sulfonamides Against Trypanosoma brucei

ACS Medicinal Chemistry Letters

Volumn 5, Issue 5, 2014, Pages 496-500

  Rashad, Adel A ^a   Jones, Amy J ^b   Avery, Vicky M ^b   Baell, Jonathan ^c   Keller, Paul A ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b GRIFFITH UNIVERSITY   (Australia)

^c MONASH UNIVERSITY   (Australia)

Author keywords

SAR; sulfonamides; T. brucei; tetrahydroquinoline

Indexed keywords

ANTIPARASITIC AGENT; METHYL GROUP; SULFONAMIDE; TETRAHYDROISOQUINOLINE DISULFONAMIDE; UNCLASSIFIED DRUG;

AFRICAN TRYPANOSOMIASIS; ANIMAL CELL; ARTICLE; CENTRAL NERVOUS SYSTEM; CLUSTER ANALYSIS; CYTOTOXICITY; DRUG DEVELOPMENT; DRUG PENETRATION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH THROUGHPUT SCREENING; HYDROPHOBICITY; IC 50; MEDICINAL CHEMISTRY; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA BRUCEI;

EID: 84900414255     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml400487t     Document Type: Article

References (23)

1. Cecchi, G.; Paone, M.; Franco, J. R.; Fevre, E. M.; Diarra, A.; Ruiz, J. A.; Mattioli, R. C.; Simarro, P. P. Towards the Atlas of human African trypanosomiasis Int. J. Health. Geogr. 2009, 8, 15
2. Brun, R.; Blum, J.; Chappuis, F.; Burri, C. Human African trypanosomiasis Lancet 2010, 375, 148-159
3. Simarro, P. P.; Cecchi, G.; Franco, J. R.; Paone, M.; Diarra, A.; Ruiz-Postigo, J. A.; Fevre, E. M.; Mattioli, R. C.; Jannin, J. G. Estimating and mapping the population at risk of sleeping sickness PLoS Negl. Trop. Dis. 2012, 6, e1859
4. Popejoy, M. W. Working to Overcome the Global Impact of Neglected Tropical Diseases Perspect. Public Heal. 2012, 132, 192-192
5. Wastling, S. L.; Welburn, S. C. Diagnosis of human sleeping sickness: sense and sensitivity Trends Parasitol. 2011, 27, 394-402
6. Phillips, M. A. Stoking the drug target pipeline for human African trypanosomiasis Mol. Microbiol. 2012, 86, 10-14
7. Croft, S. L.; Barrett, M. P.; Urbina, J. A. Chemotherapy of trypanosomiases and leishmaniasis Trends Parasitol. 2005, 21, 508-512
8. Renslo, A. R.; McKerrow, J. H. Drug discovery and development for neglected parasitic diseases Nat. Chem. Biol. 2006, 2, 701-710
9. Pepin, J.; Milord, F. The treatment of human African trypanosomiasis Adv. Parasitol. 1994, 33, 1-47
10. Barrett, M. P. Potential new drugs for human African trypanosomiasis: some progress at last Curr. Opin. Infect. Dis. 2010, 23, 603-608
11. 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, non-inferiority trial Lancet 2009, 374, 56-64
12. Yun, O.; Priotto, G.; Tong, J.; Flevaud, L.; Chappuis, F. NECT is next: Implementing the new drug combination therapy for Trypanosoma brucei gambiense sleeping sickness PLoS Neglect. Trop. Dis. 2010, 4, e720
13. Delespaux, V.; de Koning, H. P. Drugs and drug resistance in African trypanosomiasis Drug Resist. Update 2007, 10, 30-50
14. Rodgers, J. Human African trypanosomiasis, chemotherapy and CNS disease J. Neuroimmunol. 2009, 211, 16-22
15. Wenzler, T.; Boykin, D. W.; Ismail, M. A.; Hall, J. E.; Tidwell, R. R.; Brun, R. New treatment option for second-stage African sleeping sickness: In vitro and in vivo efficacy of aza analogs of DB289 Antimicrob. Agents Chemother. 2009, 53, 4185-4192
16. Torreele, E.; Trunz, B. B.; Tweats, D.; Kaiser, M.; Brun, R.; Mazue, G.; Bray, M. A.; Pecoul, B. Fexinidazole: A new oral nitroimidazole drug candidate entering clinical development for the treatment of sleeping sickness PLoS Neglect. Trop. Dis. 2010, 4, e923
17. Jacobs, R. T.; Nare, B.; Wring, S. A.; Orr, M. D.; Chen, D.; Sligar, J. M.; Jenks, M. X.; Noe, R. A.; Bowling, T. S.; Mercer, L. T.; Rewerts, C.; Gaukel, E.; Owens, J.; Parham, R.; Randolph, R.; Beaudet, B.; Bacchi, C. J.; Yarlett, N.; Plattner, J. J.; Freund, Y.; Ding, C.; Akama, T.; Zhang, Y. K.; Brun, R.; Kaiser, M.; Scandale, I.; Don, R. SCYX-7158, an orally-active benzoxaborole for the treatment of stage 2 human African trypanosomiasis PLoS Neglect. Trop. Dis. 2011, 5, e1151
18. Ettari, R.; Tamborini, L.; Angelo, I. C.; Micale, N.; Pinto, A.; De Micheli, C.; Conti, P. Inhibition of Rhodesain as a Novel Therapeutic Modality for Human African Trypanosomiasis J. Med. Chem. 2013, 56, 5637-5658
19. Sykes, M. L.; Baell, J. B.; Kaiser, M.; Chatelain, E.; Moawad, S. R.; Ganame, D.; Ioset, J. R.; Avery, V. M. Identification of compounds with anti-proliferative activity against Trypanosoma brucei brucei Strain 427 by a whole cell viability based HTS campaign PLoS Neglect. Trop. Dis. 2012, 6, e1896
20. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 2001, 46, 3-26
21. Gamble, A. B.; Garner, J.; Gordon, C. P.; O'Conner, S. M. J.; Keller, P. A. Aryl nitro reduction with iron powder or stannous chloride under ultrasonic irradiation Synth. Commun. 2007, 37, 2777-2786
22. Buchstaller, H. P.; Siebert, C. D.; Steinmetz, R.; Frank, I.; Berger, M. L.; Gottschlich, R.; Leibrock, J.; Krug, M.; Steinhilber, D.; Noe, C. R. Synthesis of thieno[2,3-b]pyridinones acting as cytoprotectants and as inhibitors of [H-3]Glycine binding to the N -methyl- d -aspartate (NMDA) receptor J. Med. Chem. 2006, 49, 864-871
23. Hwang, K. J.; Lee, T. S.; Kim, K. W.; Kim, B. T.; Lee, C. M.; Park, E. Y.; Woo, R. S. 4-Hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b] pyrimidine derivatives: Synthesis and their biological evaluation for the glycine site acting on the N -methyl- d -aspartate (NMDA) receptor Arch. Pharm. Res. 2001, 24, 270-275