Skip to main navigation menu Skip to main content Skip to site footer
##common.pageHeaderLogo.altText##

Articles

Vol. 1 No. 1 (2010): January-March 2010

Synthesis and Antitubercular Activity of 5-benzyl-3-phenyl dihydroisoxazoles

DOI
https://doi.org/10.37285/ijddd.1.1.2
Submitted
October 30, 2024
Published
2010-10-15

Abstract

Hetero Diels-Alder reaction of aromatic aldoximes with different alkenes resulted in highly substituted dihydroisoxazoles (1-12) in good yields. All the compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Ra and H37Rv. Compounds 2, 3, 6, and 10 exhibited antitubercular activity with minimum inhibitory concentration (MIC) ranging from 12.5 to 3.12 g/mL against the infectious strain M. tuberculosis H37Rv.

References

  1. 1. (a) Nunn, P.; Williams, B.; Floyd, K.; Dye, C.; Elzinga, G.; Raviglione, M. Nat. Rev. Immunol. 2005, 5, 819; (b) Tripathi, R.P.; Tewari, N.; Dwivedi, N.; Twari, V.K. Med. Res. Rev. 2005, 25, 93; (c) Dye, C. Lancet 2006, 367, 938 ; (d) Gandhi, N. R. Lancet 2006, 368, 1575.
  2. 2. Raviglione, M.C.; Snider, Jr.D.E.; Kochi. A. JAMA 1997, 273, 377.
  3. 3. (a) Farmer, P.; Bayona, J.; Beccera, M.; Henry, J.; Furin, C.; Hiarr, H.; Kim, J. Y.; Mimic, C.; Nardell, E.; Shin, S. Int. J. Tuberc. Lung Dis. 1998, 2, 689; (b) Dooley S.W.; Jarvis, W.R.; Martone W.J.; Snyder Jr.,D.E. Ann. Intern. Med. 1997, 117, 257.
  4. 4. (a) Barbachyn, M.R.; Cleek, G.J.; Dolak, L.A.; Garmon,
  5. S. A.; Morris, J.; Seest, E.P.; Thomas, R.C.; Toops, D.S.; Watt, W.; Wishka, D.G.; Ford, C.W.; Zurenko, G.E.; Hamel, J.C.; Schaadt, R.D.; Stapert, D.; Yagi, B.H.;1. (a) Nunn, P.; Williams, B.; Floyd, K.; Dye, C.; Elzinga, G.; Raviglione, M. Nat. Rev. Immunol. 2005, 5, 819; (b) Tripathi, R.P.; Tewari, N.; Dwivedi, N.; Twari, V.K. Med. Res. Rev. 2005, 25, 93; (c) Dye, C. Lancet 2006, 367, 938 ; (d) Gandhi, N. R. Lancet 2006, 368, 1575.
  6. 2. Raviglione, M.C.; Snider, Jr.D.E.; Kochi. A. JAMA 1997, 273, 377.
  7. 3. (a) Farmer, P.; Bayona, J.; Beccera, M.; Henry, J.; Furin, C.; Hiarr, H.; Kim, J. Y.; Mimic, C.; Nardell, E.; Shin, S. Int. J. Tuberc. Lung Dis. 1998, 2, 689; (b) Dooley S.W.; Jarvis, W.R.; Martone W.J.; Snyder Jr.,D.E. Ann. Intern. Med. 1997, 117, 257.
  8. 4. (a) Barbachyn, M.R.; Cleek, G.J.; Dolak, L.A.; Garmon,
  9. S. A.; Morris, J.; Seest, E.P.; Thomas, R.C.; Toops, D.S.; Watt, W.; Wishka, D.G.; Ford, C.W.; Zurenko, G.E.; Hamel, J.C.; Schaadt, R.D.; Stapert, D.; Yagi, B.H.;1. (a) Nunn, P.; Williams, B.; Floyd, K.; Dye, C.; Elzinga, G.; Raviglione, M. Nat. Rev. Immunol. 2005, 5, 819; (b) Tripathi, R.P.; Tewari, N.; Dwivedi, N.; Twari, V.K. Med. Res. Rev. 2005, 25, 93; (c) Dye, C. Lancet 2006, 367, 938 ; (d) Gandhi, N. R. Lancet 2006, 368, 1575.
  10. 2. Raviglione, M.C.; Snider, Jr.D.E.; Kochi. A. JAMA 1997, 273, 377.
  11. 3. (a) Farmer, P.; Bayona, J.; Beccera, M.; Henry, J.; Furin, C.; Hiarr, H.; Kim, J. Y.; Mimic, C.; Nardell, E.; Shin, S. Int. J. Tuberc. Lung Dis. 1998, 2, 689; (b) Dooley S.W.; Jarvis, W.R.; Martone W.J.; Snyder Jr.,D.E. Ann. Intern. Med. 1997, 117, 257.
  12. 4. (a) Barbachyn, M.R.; Cleek, G.J.; Dolak, L.A.; Garmon,
  13. S. A.; Morris, J.; Seest, E.P.; Thomas, R.C.; Toops, D.S.; Watt, W.; Wishka, D.G.; Ford, C.W.; Zurenko, G.E.; Hamel, J.C.; Schaadt, R.D.; Stapert, D.; Yagi, B.H.;Adams, W.J.; Friis, J.M.; Slatter, J.G.; Sams, J.P.; Oien, N.L.; Zaya, M.J.; Wienkers, L.C.; Wynalda M.A. J. Med. Chem. 2003, 46, 284; (b) Mishra, R.C.; Tewari, N.; Verma, S.S.; Kumar, M.; Shukla, P.K. J. Carb. Chem. 2004, 23, 353; (c) Varshney, V.; Mishra, N. N.; Shukla, P. K.; Sahu, D. P. Bioorg. Med. Chem. Lett. 2009, 19, 3573. 5. Tangallapally, R.P.; Sun, D.; Rakesh.; Budha, N.; Lee, R.E.B.; Lenaerts, A.J.M.; Meibohma, B.; Lee, R.E. Bioorg. Med. Chem. Lett. 2007, 17, 6638.
  14. 6. Lu, Y.; Miller, M.J. Bioorg. Med. Chem. 1999, 7, 3025.
  15. 7. Andres, J.I.; Alcazar, J.; Alonso, J.M.; Alvarez, R.M.; Cid, J.M.; Lucas, A.I.D.; Fernandez, J.; Martınez, S.; Nieto, C.; Pastor, J.; Bakker, M.H.; Biesmans, I.; Heylen,
  16. L. I.; and Megens, A.A.; Bioorg. Med. Chem. Lett. 2003, 13, 2719.
  17. 8. Schaller, C.; Demange, R.; Picasso, S.; and Vogel, P.; Bioorg. Med. Chem. Lett. 1999, 9, 277.
  18. 9. Lee, J.; Kang, S.U.; Kim, S.Y.; Kim, S.E.; Job, Y.J.; and Kim, S. Bioorg. Med. Chem. Lett. 2001, 11, 965.
  19. 10. (a) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2003, 44, 8417; (b) Sadashiva, B.P.S.; Mantelingu, K.; Nanjunda, S.S.; Rangappa, K.S. Bioorg. Med. Chem. 2003, 11, 4539; (c) Ulgheri, F.; Bacsa, J.; Nassimbeni, L.; Spanu, P. Tetrahedron Lett. 2003, 44, 671.
  20. 11. Frederickson, M. Tetrahedron 1997, 53, 403.
  21. 12. Saha, A.; Bhattacharjya, A. Chem. Commun. 1997, 495.
  22. 13. (a) Lin, A.H.; Murray, R.W.; Vidmar, T.J.; Marotti, K.R. Antimicrob. Agents Chemother. 1997, 41, 2127; (b) Diekema, D.J.; Jones, R.N. Lancet 2001, 358, 1975.
  23. 14. (a) Hancock, R.E. Lancet Infect. Dis. 2005, 5, 209; (b) Stevens, D.L.; Dotter, B.; Madaras-Kelly, K. Exp. Rev. Ant. Infect. Ther. 2004, 2, 51.
  24. 15. (a) Gonzales, R.D.; Scherkenberger, P.C.; Graham, M.B.; Kelkar, S.; DenBesten, K.; Quinn, J.P. Lancet 2001, 357, 1179; (b) Tsiodras, S.; Gold, H.S.; Sakoulas, G.; Eliopoulus, G.M.; Wenne rsten, C.; Venkatraman, L.; Moellering, R.C., Jr.; Ferraro, M.J. Lancet 2001, 35, 207;
  25. (c) Mankin, A.; Toh, S.; Xiong, L.; Lolans, K.; Quinn, J. Intersci. Conf. Antimicrob. Agents Chemother. 2006, 46, C1–942.
  26. 16. Zhang, P.Z.; Li X. L.; Chen, H.; Li, Y.N.; Wang, R. Tetrahedron Lett. 2007, 48, 7813, references cited therein.
  27. 17. Collins, L.A.; Franzblan, S.G. Antimicrob. Agents Chemother. 1997, 41, 1004.
  28. 18. Saito, H.; Tomioka, H.; Sato, K.; Emori, M.; Yamane, T.; Yamashita, K. Antimicrob. Agents Chemother. 1991, 35,542.

Similar Articles

<< < 1 2 

You may also start an advanced similarity search for this article.