Synthesis, optimization and structure-activity relationships of 3,5-disubstituted isoxazolines as new anti-tuberculosis agents

European Journal of Medicinal Chemistry

Volumn 44, Issue 2, 2009, Pages 460-472

  Rakesh, ^a   Sun, Dianqing ^a   Lee, Robin B ^a   Tangallapally, Rajendra P ^a   Lee, Richard E ^a  

^a UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

Author keywords

Anti tuberculosis agents; Antibacterial; Isoxazolines; Lead optimization; Nitrofurans

Indexed keywords

4 [4 (3 ETHOXYCARBONYL 4,5 DIHYDROISOXAZOL 5 YL)PHENYL]PIPERAZINE 1 CARBOXYLIC ACID ALLYL ESTER; 4 [4 (3 ETHOXYCARBONYL 4,5 DIHYDROISOXAZOL 5 YL)PHENYL]PIPERAZINE 1 CARBOXYLIC ACID BUTYL ESTER; 4 [4 (3 ETHOXYCARBONYL 4,5 DIHYDROISOXAZOL 5 YL)PHENYL]PIPERAZINE 1 CARBOXYLIC ACID ISOBUTYL ESTER; 5 [4 (4 HEXYLCARBAMOYLPIPERAZIN 1 YL)PHENYL] 4,5 DIHYDROISOXAZOLE 3 CARBOXYLIC ACID ETHYL ESTER; ISOXAZOLINE DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

AMIDES; ANTITUBERCULAR AGENTS; FURANS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; OXAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 60149090334     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.04.007     Document Type: Article

References (21)

1. Dye C., Scheele S., Dolin P., et al. Global burden of tuberculosis. Estimated incidence, prevalence, and mortality by country. J. Am. Med. Assoc. 282 7 (1999) 677-686
2. Murray J.F. Tuberculosis and HIV infection: a global perspective. Respiration 65 2 (1998) 335-342
3. " Tuberculosis" WHO Fact Sheet No 104 (2006), Health Communications, WHO, Geneva. http://www.who.int/mediacentre/factsheets/fs104/en/index.html
4. In: Bloom B.R. (Ed). Tuberculosis: Pathogenesis, Protection, and Control (1994), ASM Press, Washington, DC
5. Sacchettini J.C., Rubin E.J., and Freundlich J.S. Nat. Rev. Microbiol. 6 1 (2008) 41-52
6. Burman W.J., and Jones B.E. Am. J. Respir. Crit. Care Med. 164 (2001) 7-12
7. Spigelman M.K. J. Infect. Dis. 196 (2007) S28-S34
8. Tangallapally R.P., Yendapally R., Lee R.E., Hevener K., Jones V.C., Lenaerts A.J.M., McNeil M.R., Wang Y., Franzblau S., and Lee R.E. J. Med. Chem. 47 (2004) 5276-5283
9. Tangallapally R.P., Yendapally R., Lee R.E.B., Lenaerts A.J.M., and Lee R.E. J. Med. Chem. 48 (2005) 8261-8269
10. Tangallapally R.P., Lee R.E.B., Lenaerts A.J.M., and Lee R.E. Bioorg. Med. Chem. Lett. 16 (2006) 2584-2589
11. Tangallapally R.P., Yendapally R., Daniels A.J., Lee R.E.B., and Lee R.E. Curr. Top. Med. Chem. 7 (2007) 509-526
12. Tangallapally R.P., Sun D., Rakesh, Budha N., Lee R.E.B., Lenaerts A.J.M., Meibohm B., and Lee R.E. Bioorg. Med. Chem. Lett. 17 (2007) 6638-6642
13. Renslo A.R., Luehr G.W., and Gordeev M.F. Bioorg. Med. Chem. 14 (2006) 4227-4240
14. Sood R., Bhadauriya T., Rao M., Gautam R., Malhotra S., Barman T.K., Upadhyay D.J., and Rattan A. Infect. Disord. Drug Targets 6 (2006) 343-354
15. Zappia G., Menendez P., Delle Monache G., Misiti D., Nevola L., and Botta B. Mini Rev. Med. Chem. 7 (2007) 389-409
16. Guram A.A., Rennels R.A., and Buchwald S.L. Angew. Chem., Int. Ed. Engl. 34 (1995) 1348-1350
17. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry (1984), Wiley, New York
18. Diana G.D., Rudewicz P., Pevear D.C., Nitz T.J., Aldous S.C., Aldous D.J., Robinson D.T., Draper T., Dutko F.J., Aldi C., Gendron G., Oglesby R.C., Volkots D.L., Reuman M., Bailey T.R., Czerniak R., Block T., Roland R., and Oppermann J. J. Med. Chem. 38 (1995) 1355-1371
19. Lee R.E., Protopopova M., Crooks E., Slayden R.A., Terrot M., and Barry III C.E. J. Comb. Chem. 5 (2003) 172-187
20. Sasaki H., Haraguchi Y., Itotani M., Kuroda H., Hashizume H., Tomishige T., Kawasaki M., Matsumoto M., Komatsu M., and Tsubouchi H. J. Med. Chem. 49 (2006) 7854-7860
21. Fortun J., Davila P.M., Navas E., Perez-Elias M.J., Cobo J., Tato M., De la Pedrosa E.G., Gomez-Mampaso E., and Moreno S. J. Antimicrob. Chemother. 56 (2005) 180-185