Synthesis of new and potent analogues of anti-tuberculosis agent 5-nitro-furan-2-carboxylic acid 4-(4-benzyl-piperazin-1-yl)-benzylamide with improved bioavailability

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 10, 2006, Pages 2584-2589

  Tangallapally, Rajendra P ^a   Lee, Robin E B ^a   Lenaerts, Anne J M ^b   Lee, Richard E ^a  

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

^b Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

Antibiotic; Bioavailability; Nitrofuran; Tuberculosis

Indexed keywords

5 NITROFURAN 2 CARBOXYLIC ACID 4 (4 BENZYLPIPERAZIN 1 YL)BENZYLAMIDE; BENZYL DERIVATIVE; CARBAMIC ACID; ISOQUINOLINE DERIVATIVE; NITROGEN; PIPERAZINE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UREA;

ARTICLE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG SYNTHESIS; SUBSTITUTION REACTION;

ANIMALS; ANTITUBERCULAR AGENTS; BIOLOGICAL AVAILABILITY; MICE; MICROBIAL SENSITIVITY TESTS; PIPERAZINES;

EID: 33645887824     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.02.048     Document Type: Article

References (14)

1. World Health Organization Global Tuberculosis Programme (2005) WHO Report on the Tuberculosis Epidemic 2005 (WHO, Geneva).
2. Murray C.J.L., and Salomon J.A. Proc. Natl. Acad. Sci. U.S.A. (1998) 13881
3. Murray C.J.L., and Lopez A.D. Science 274 (1996) 740
4. Pablos-Méndez A., Raviglione M.C., Laszlo A., Binkin N., Rieder H.L., Bustreo F., Cohn D.L., Lambregts-van Weezenbeek C.S.B., Kim S.J., Chaulet P., and Nunn P. N. Eng. J. Med. 338 (1998) 1641
5. Tangallapally R.P., Lee R.E., Yendapally R., 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
6. Tangallapally R.P., Yendapally R., Lee R.E., Lenaerts A.J.M., and Lee R.E. J. Med. Chem. 48 (2005) 8261
7. Brown G.R., Foubister A.J., and Ratcliffe P.D. Tetrahedron Lett. 40 (1999) 1219
8. Klenke B., and Gilbert I.H. J. Org. Chem. 66 (2001) 2480
9. Boswell Jr. R.F., Helsley G.C., Duncan Jr. R.L., Funderburk W.H., and Johnson D.N. J. Med. Chem. 17 (1974) 1000
10. Yoshinori M., Hiroshi S., Naoto H., Yoshio I., Masahiko S., and Tsunehiko N. J. Labelled Compd. Radiopharm. 43 (2000) 983
11. 3): δ 3.02 (t, J = 6.59 Hz, 2H), 3.60 (dt, J = 2.29, 6.83 Hz, 2H), 6.08-6.15 (br s, 1H), 6.93 (dd, J = 2.68, 9.03 Hz, 1H), 7.04 (dt, J = 2.68, 8.54 Hz, 1H), 8.1 (dd, J = 5.85, 8.54 Hz, 1H); ESI-MASS: 188.3 (M+23).
12. Lee R.E., Protopopova M., Crooks E., Slayden R.A., Terrot M., and Barry III C.E. J. Comb. Chem. 5 (2003) 172
13. Gruppo, V.; Johnson, C. M.; Marietta, K. S.; Scherman, H.; Zink, E. E.; Crick, D. C.; Adams, L. B.; Orme, I. M.; Lenaerts, A. J. Antimicrob. Agents Chemother., in press.
14. 4: C, 61.61; H, 5.99; N, 15.13. Found: C, 61.47; H, 5.99; N, 15.03.