Synthesis, biological evaluation, and structure-activity relationships of N -benzoyl-2-hydroxybenzamides as agents active against P. falciparum (K1 strain), trypanosomes, and leishmania

Journal of Medicinal Chemistry

Volumn 55, Issue 7, 2012, Pages 3088-3100

  Stec, Jozef ^a   Huang, Qingqing ^a   Pieroni, Marco ^a   Kaiser, Marcel ^b,c   Fomovska, Alina ^d   Mui, Ernest ^d   Witola, William H ^d   Bettis, Samuel ^e   McLeod, Rima ^d   Brun, Reto ^b,c   Kozikowski, Alan P ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

^c UNIVERSITY OF BASEL   (Switzerland)

^d UNIVERSITY OF CHICAGO   (United States)

^e UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXY N (4 ISOPROPYLBENZOYL)BENZAMIDE; 2 HYDROXY N (4 METHOXYBENZOYL)BENZAMIDE; 2 HYDROXY N (4 METHYLBENZOYL)BENZAMIDE; 2 HYDROXY N (4 MORPHOLINOBENZOYL)BENZAMIDE; 2 HYDROXY N (4 NITROBENZOYL)BENZAMIDE; 2 HYDROXY N [4 (METHYLSULFONYL)BENZOYL]BENZAMIDE; 2 HYDROXY N [4 (TRIFLUOROMETHOXY)BENZOYL]BENZAMIDE; 2 HYDROXY N [4 (TRIFLUOROMETHYL)BENZOYL]BENZAMIDE; ANTIPROTOZOAL AGENT; BENZAMIDE DERIVATIVE; BENZNIDAZOLE; CHLOROQUINE; MELARSOPROL; METHYL 4 [(2 HYDROXYBENZOYL)CARBAMOYL]BENZOATE; MILTEFOSINE; N (2 HYDROXYBENZOYL) 2 NAPHTHAMIDE; N (2 HYDROXYBENZOYL) 6 METHOXY 2 NAPHTHAMIDE; N (2 HYDROXYBENZOYL)(1,1' BIPHENYL) 4 CARBOXAMIDE; N (4 BUTOXYBENZOYL) 2 HYDROXYBENZAMIDE; N (4 CYANOBENZOYL) 2 HYDROXYBENZAMIDE; N (4 ETHOXYBENZOYL) 2 HYDROXYBENZAMIDE; N (4 ETHYLBENZOYL) 2 HYDROXYBENZAMIDE; N (4 FLUOROBENZOYL) 2 HYDROXYBENZAMIDE; N (4 TERT BUTYLBENZOYL) 2 HYDROXYBENZAMIDE; N [3 (CHLOROMETHYL)BENZOYL] 2 HYDROXYBENZAMIDE; N [4 (BENZYLOXY)BENZOYL] 2 HYDROXYBENZAMIDE; N [4 (DIETHYLAMINO)BENZOYL] 2 HYDROXYBENZAMIDE; N [4 (DIMETHYLAMINO)BENZOYL] 2 HYDROXYBENZAMIDE; N BENZOYL 2 HYDROXYBENZAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; LEISHMANIA DONOVANI; NONHUMAN; PLASMODIUM FALCIPARUM; RAT; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA CRUZI; TRYPANOSOMA RHODESIENSE;

ANTIMALARIALS; BENZAMIDES; IMIDES; LEISHMANIA DONOVANI; PARASITIC SENSITIVITY TESTS; PLASMODIUM FALCIPARUM; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOCIDAL AGENTS; TRYPANOSOMA; TRYPANOSOMA BRUCEI RHODESIENSE; TRYPANOSOMA CRUZI;

EID: 84859798409     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2015183     Document Type: Article

References (21)

1. Fomovska, A.; Huang, Q.; Bissati, K. E.; Mui, E. J.; Witola, W. H.; Cheng, G.; Zhou, Y.; Sommerville, C.; Roberts, C. W.; Bettis, S.; Prigge, S. T.; Afanador, G. A.; Hickman, M. R.; Lee, P. J.; Leed, S. E.; Auschwitz, J. M.; Pieroni, M.; Stec, J.; Muench, S. P.; Rice, D. W.; Kozikowski, A. P.; McLeod, R. Novel N -benzoyl-2-hydroxybenzamide disrupts unique parasite secretory pathway Antimicrob. Agents Chemother. 2012, 10.1128/AAC.06450-11
2. Working to Overcome the Global Impact of Neglected Tropical Diseases: First WHO Report on Neglected Tropical Diseases; World Health Organization: Geneva, 2010.
3. Brun, R.; Blum, J.; Chappuis, F.; Burri, C. Human African trypanosomiasis Lancet 2010, 375, 148-159
4. Stuart, K.; Brun, R.; Croft, S.; Fairlamb, A.; GuIrtler, R. E.; McKerrow, J.; Reed, S.; Tarleton, R. Kinetoplastids: related protozoan pathogens, different diseases J. Clin. Invest. 2008, 118, 1301-1310
5. Malaria Fact sheet No. 94; World Health Organization: Geneva, 2011.
6. Rathore, D.; Jani, D.; Nagarkatti, R. Novel therapeutic target for protozoal diseases. U.S. Patent US20070148185 (A1), 2007.
7. Adagu, I. S.; Nolder, D.; Warhurst, D. C.; Rossignol, J. F. In vitro activity of nitazoxanide and related compounds against isolates of Giardia intestinalis, Entamoeba histolytica and Trichomonas vaginalis J. Antimicrob. Chemother. 2002, 49, 103-111
8. Cortes, H. C.; Mueller, N.; Esposito, M.; Leitao, A.; Naguleswaran, A.; Hemphill, A. In vitro efficacy of nitro- and bromo-thiazolyl-salicylamide compounds (thiazolides) against Besnoitia besnoiti infection in Vero cells Parasitology 2007, 134, 975-985
9. Esposito, M.; Moores, S.; Naguleswaran, A.; Muller, J.; Hemphill, A. Induction of tachyzoite egress from cells infected with the protozoan Neospora caninum by nitro- and bromo-thiazolides, a class of broad-spectrum anti-parasitic drugs Int. J. Parasitol. 2007, 37, 1143-1152
10. Fonseca-Salamanca, F.; Martinez-Grueiro, M. M.; Martinez-Fernandez, A. R. Nematocidal activity of nitazoxanide in laboratory models Parasitol. Res. 2003, 91, 321-324
11. Roberts, C. W.; Roberts, F.; Henriquez, F. L.; Akiyoshi, D.; Samuel, B. U.; Richards, T. A.; Milhous, W.; Kyle, D.; McIntosh, L.; Hill, G. C.; Chaudhuri, M.; Tzipori, S.; McLeod, R. Evidence for mitochondrial-derived alternative oxidase in the apicomplexan parasite Cryptosporidium parvum: a potential antimicrobial agent target Int. J. Parasitol. 2004, 34, 297-308
12. Cai, Z. R.; Jabri, S. Y.; Jin, H.; Kim, C. U.; Lansdown, R. A.; Metobo, S. E.; Mish, M. R.; Pastor, R. M. Integrase inhibitor compounds. Patent WO 2006/125048 A2, 2006.
13. Wittich, S.; Scherf, H.; Xie, C.; Brosch, G.; Loidl, P.; GerhaIuser, C.; Jung, M. Structure-activity relationships on phenylalanine-containing inhibitors of histone deacetylase: in vitro enzyme inhibition, induction of differentiation, and inhibition of proliferation in Friend leukemic cells J. Med. Chem. 2002, 45, 3296-3309
14. Hossain, N. Novel tricyclic spiroderivatives as modulators of chemokine receptor activity. Patent WO 2005/037814 (A1), 2005.
15. Qiao, C.; Gupte, A.; Boshoff, H. I.; Wilson, D. J.; Bennett, E. M.; Somu, R. V.; Barry, C. E.; Aldrich, C. C. 5a- O -[(N -Acyl)sulfamoyl]adenosines as antitubercular agents that inhibit MbtA: an adenylation enzyme required for siderophore biosynthesis of the mycobactins J. Med. Chem. 2007, 50, 6080-6094
16. Adler, T.; Bonjoch, J.; Clayden, J.; Font-Bardia, M.; Pickworth, M.; Solans, X.; Sole, D.; Vallverdu, L. Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines Org. Biomol. Chem. 2005, 3, 3173-3183
17. Kline, T.; Fromhold, M.; McKennon, T. E.; Cai, S.; Treiberg, J.; Ihle, N.; Sherman, D.; Schwan, W.; Hickey, M. J.; Warrener, P.; Witte, P. R.; Brody, L. L.; Goltry, L.; Barker, L. M.; Anderson, S. U.; Tanaka, S. K.; Shawar, R. M.; Nguyen, L. Y.; Langhorne, M.; Bigelow, A.; Embuscado, L.; Naeemi, E. Antimicrobial effects of novel siderophores linked to beta-lactam antibiotics Bioorg. Med. Chem. 2000, 8, 73-93
18. Hanessian, S.; Liak, T. J.; Vanasse, B. Facile cleavage of benzyl ethers by catalytic transfer hydrogenation Synthesis 1981, 396-397
19. Orhan, I.; Sener, B.; Kaiser, M.; Brun, R.; Tasdemir, D. Inhibitory activity of marine sponge-derived natural products against parasitic protozoa Mar. Drugs 2010, 8, 47-58
20. Qu, J.; Kumar, N.; Alamgir, M.; Black, D. S. A versatile synthetic route to 11 H -indolo[3,2- c ]isoquinolines Tetrahedron Lett. 2009, 50, 5628-5630
21. Vasudevan, A.; Souers, A. J.; Freeman, J. C.; Verzal, M. K.; Gao, J.; Mulhern, M. M.; Wodka, D.; Lynch, J. K.; Engstrom, K. M.; Wagaw, S. H.; Brodjian, S.; Dayton, B.; Falls, D. H.; Bush, E.; Brune, M.; Shapiro, R. D.; Marsh, K. C.; Hernandez, L. E.; Collins, C. A.; Kym, P. R. Aminopiperidine indazoles as orally efficacious melanin concentrating hormone receptor-1 antagonists Bioorg. Med. Chem. Lett. 2005, 15, 5293-5297