Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Microwave Synthesis of Chiral N-Benzyl-2-methyl-2H-benzo[b][1,4]oxazin/thiazin-3(4H)-ones via Smiles Rearrangement and their Biological Evaluation

  • Meng, Li-Juan (Departments of Chemistry and Physics, Changwon National University) ;
  • Zuo, Hua (College of Pharmaceutical Sciences, Southwest University) ;
  • Vijaykumar, B.V.D. (Departments of Chemistry and Physics, Changwon National University) ;
  • Dupati, Gautam (Departments of Chemistry and Physics, Changwon National University) ;
  • Choi, Kyung-Min (Departments of Chemistry and Physics, Changwon National University) ;
  • Jang, Kiwan (Departments of Chemistry and Physics, Changwon National University) ;
  • Yoon, Yong-Jin (Department of Chemistry, Gyeongsang National University) ;
  • Shin, Dong-Soo (Departments of Chemistry and Physics, Changwon National University)
  • Received : 2012.10.10
  • Accepted : 2012.11.29
  • Published : 2013.02.20
Download PDF
⟨ Previous Next ⟩

Abstract

Optically active N-benzyl-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-ones and N-benzyl-2-methyl-2H-benzo[b][1,4]thiazin-3(4H)-ones with potential synthetic and pharmacological interest were prepared via Smiles rearrangement in conventional as well as microwave irradiation conditions in one-pot from inexpensive (S)-2-chloropropionic acid. Most of the compounds displayed good inhibition against Gram positive bacteria and fungi in the antibiotic test.

Keywords

References

  1. Katsura, Y.; Nishino, S.; Takasugi, H. Chem. Pharm. Bull. 1991, 11, 2937.
  2. Kajino, N.; Shibouta, Y.; Nishikawa, K.; Meguro, K. Chem. Pharm. Bull. 1991, 11, 2896.
  3. Fringuelli, R.; Pietrella, D.; Schiaffella, F.; Guarraci, A; Perito, S.; Bistoni, F.; Vecchiarelli, A. Bioorg. Med. Chem. 2002, 10, 1681. https://doi.org/10.1016/S0968-0896(02)00038-X
  4. Macchiarulo, A.; Costantino, G.; Fringuelli, D.; Vecchiarelli, A.; Schiaffella F.; Fringuelli, R. Bioorg. Med. Chem. 2002, 10, 3415. https://doi.org/10.1016/S0968-0896(02)00263-8
  5. Nair, M. G.; Salter, O. C.; Kisliuk, R. L.; Gaumont, Y. J. Med. Chem. 1983, 26, 1164. https://doi.org/10.1021/jm00362a015
  6. Wahidulla, S.; Bhattacharjee, J. J. J. Indian Inst. Sci. 2001, 81, 485.
  7. Andreas, S.; Thierry, B. DE102004019540, November 10, 2005.
  8. ROGER, F.; Ann, W. W. M. US5854242, December 29, 1998.
  9. Buckman, B. O.; Mohan, R.; Koovakkat, S. Bioorg. Med. Chem. Lett. 1998, 8, 2235. https://doi.org/10.1016/S0960-894X(98)00386-2
  10. Zhao, S. H.; Berger, J.; Clark, R. D.; Sethofer, S. G.; Krauss, N. E.; Brothers, J. M.; Martin, R. S.; Misner, D. L.; Schwabd, D.; Alexandrovad, L. Bioorg. Med. Chem. Lett. 2007, 17, 3504. https://doi.org/10.1016/j.bmcl.2006.12.093
  11. Dougherty, K. J.; Bannatyne, B. A.; Jankowska, E.; Krutki, P.; Maxwell, D. J. J. Neurosci. 2005, 25, 584.
  12. Chiu, H. I.; Lin, Y. C.; Cheng, C. Y.; Tsai, M. C.; Yu, H. C. Bioorg. Med. Chem. Lett. 2001, 9, 383. https://doi.org/10.1016/S0968-0896(00)00260-1
  13. Caliendo, G.; Perissutti, E.; Santagada, V.; Fiorino, F.; Severino, B.; Cirillo, D.; Bianca, R. E. V.; Lippolis, L.; Pinto, A.; Sorrentino, R. Eur. J. Med. Chem. 2004, 39, 815. https://doi.org/10.1016/j.ejmech.2004.05.003
  14. Yamamoto, T.; Hori, M, Watanabe, I.; Tsutsui, H.; Harada, K.; Ikeda, S.; Maruo, J.; Morita, T.; Ohtaka, H. Chem. Pharm. Bull. 1997, 45, 1975. https://doi.org/10.1248/cpb.45.1975
  15. Zhou, D. H.; Harrison, B. L.; Shah, U.; Andree, T. H.; Hornby, G. A.; Scerni, R.; Schechter, L. E.; Smith, D. L.; Sullivanb, K. M.; Mewshawa, R. E. Bioorg. Med. Chem. Lett. 2006, 16, 1338. https://doi.org/10.1016/j.bmcl.2005.11.054
  16. Vong, A. WO2003091248.
  17. Jones, J. H.; Anderson, P. S.; Baldwin, J. J.; Clineschmidt, B. V.; McClure, D. E.; Lundell, G. F.; Randall, W. C.; Martin, G. E.; Williams, M.; Hirshfield, J. M.; Smith, G.; Lumma, P. K. J. Med. Chem. 1984, 27, 1607. https://doi.org/10.1021/jm00378a014
  18. Stork, B.; Plekkenpol, R. H.; Niemann, L. C.; Stroomer, C. N. J.; Tulp, M. H. M.; Stuivenberg, H. H.; McCreary, A. C.; Hesselink, M. B.; Herremans, A. H. J.; Kruse, C. G. J. Med. Chem. 2005, 48, 6855. https://doi.org/10.1021/jm050148z
  19. Cornelis, B. US2005209228, September 22, 2005.
  20. Lanni, T. B., Jr.; Greene, K. L.; Kolz, C. N.; Para, K. S.; Visnick, M.; Mobley, J. L.; Dudley, D. T.; Baginskib, T. J.; Liimattab, M. B. Bioorg. Med. Chem. Lett. 2007, 17, 756. https://doi.org/10.1016/j.bmcl.2006.10.080
  21. Ohno, M.; Tanaka, Y.; Miyamoto, M.; Takeda, T.; Hoshi, K.; Yamada, N.; Ohtake, A. Bioorg. Med. Chem. 2006, 14, 2005. https://doi.org/10.1016/j.bmc.2005.10.050
  22. Christie, R. M.; Agyako, C. K.; Mitchel, K. Dyes Pigments 1995, 29, 241. https://doi.org/10.1016/0143-7208(95)00049-L
  23. Sun, X. D.; Fan, M. G.; Meng, X. J.; Knobbe, E. T. J. Photochem. Photobiol. A. 1997, 102, 213. https://doi.org/10.1016/S1010-6030(96)04480-2
  24. Huang, M. Z.; Huang, K. L.; Ren, Y. G.; Lei, M. X.; Huang, L.; Hou, Z. K.; Liu, A. P.; Ou, M. X. J. Agric. Food Chem. 2005, 53, 7908. https://doi.org/10.1021/jf051494s
  25. Guarda, V. L. M.; Perrissin, M.; Thomasson, F.; Ximenes, E. A.; Galdino, S. L.; Pitta, I. R.; Luu-Duc, C.; Barbe, J. Eur. J. Med. Chem. 2003, 38, 769. https://doi.org/10.1016/S0223-5234(03)00127-2
  26. Guarda, V. L. M.; Perrissin, M.; Thomasson, F.; Ximenes, E. A.; Galdino, S. L.; Pitta, I. R.; Luu-Duc, C. Il Farmaco 2001, 56, 689. https://doi.org/10.1016/S0014-827X(01)01113-2
  27. Pitzurra, L.; Fringuelli, R.; Perito, S.; Schiaffella, F.; Barluzzi, R.; Bistoni, F.; Vecchiarelli, A. Antimicrob. Agents Chemother. 1999, 43, 2170.
  28. Fringuelli, R.; Schiaffella, F.; FBistoni, F.; Pitzurra, L.; Vecchiarelli, A. Bioorg. Med. Chem. 1998, 6, 103. https://doi.org/10.1016/S0968-0896(97)10016-5
  29. Takeshi, Y.; Ikuo, W. WO9813357, April 02, 1998.
  30. Rainer, H.; Ulrich, L. US4595685, June 17, 1986.
  31. Ulrich, L.; Rainer, H. US4831028, May 16, 1989.
  32. Yoshitake, O.; Yoichi, K. JP9012576, January 14, 1997.
  33. Wuemachu, T.; Oshio, H. KR8200849, May 17, 1982.
  34. Cho, S.-D.; Park, Y. D.; Kim, J. J.; Lee, S. G.; Ma, C.; Song, S.-Y.; Joo, W. H.; Falck, J. R.; Shiro, M.; Shin, D.-S.; Yoon, Y. J. J. Org. Chem. 2003, 68, 7918. https://doi.org/10.1021/jo034593i
  35. Zuo, H.; Meng, L.; Ghate, M.; Hwang, K.-H.; Cho, Y. K.; Chandrashekar, S.; Reddy, Ch. R.; Shin, D.-S. Tetrahedron Lett. 2008, 49, 3827. https://doi.org/10.1016/j.tetlet.2008.03.120
  36. Zuo, H.; Li, Z.-B.; Ren, F.-K.; Falck, J. R.; Meng, L.; Ahn, C.; Shin, D.-S. Tetrahedron 2008, 64, 9669. https://doi.org/10.1016/j.tet.2008.07.059
  37. Koppenhoefer, B.; Schurig, V. Organic. Syn. 1993, 8, 119.
  38. Ma, C.; Cho, S.-D.; Falck, J. R.; Shin, D.-S. Heterocycles 2004, 63, 75. https://doi.org/10.3987/COM-03-9918
  39. Cho, S.-D.; Song, S.-Y.; Park, Y.-D.; Kim, J.-J.; Joo, W.-H.; Shiro, M.; Falck, J. R.; Shin, D.-S.; Yoon, Y.-J. Tetrahedron Lett. 2003, 44, 8995. https://doi.org/10.1016/j.tetlet.2003.09.216
  40. Cho, S.-D.; Park, Y.-D.; Kim, J.-J.; Joo, W.-H.; Shiro, M.; Esser, L.; Falck, J. R.; Ahn, C.; Yoon, Y.-J.; Shin, D.-S. Tetrahedron 2004, 60, 3763. https://doi.org/10.1016/j.tet.2004.03.011
  41. Zuo, H.; Kam, K.-H.; Kwan, H.-J.; Meng, L.; Ahn, C.; Won, T.-J.; Kim, T.- H.; Reddy, Ch. R.; Chandrashekar, S.; Shin, D.-S. Bull. Korean Chem. Soc. 2008, 29, 1379. https://doi.org/10.5012/bkcs.2008.29.7.1379

Cited by

  1. ChemInform Abstract: Microwave Synthesis of Chiral N-Benzyl-2-methyl-2H-benzo[b][1,4]oxazin/thiazin-3(4H)-ones via Smiles Rearrangement and Their Biological Evaluation. vol.44, pp.40, 2013, https://doi.org/10.1002/chin.201340187
  2. DOTMA-based amides (DOTMAMs) as a platform for the development of PARACEST MRI contrast agents vol.6, pp.67, 2016, https://doi.org/10.1039/C6RA11741D
  3. -arylated coumarin/pyran derivatives vol.42, pp.14, 2018, https://doi.org/10.1039/C8NJ02109K
  4. Smiles Rearrangement Based Practical One-pot Synthesis of N-Alkyl/aryl-6-aminoquinolines from 6-Hydroxylquinoline vol.34, pp.12, 2013, https://doi.org/10.5012/bkcs.2013.34.12.3881
  5. Docking, Synthesis, Antifungal and Cytotoxic Activities of Some Novel Substituted 4H-Benzoxazin-3-one vol.41, pp.2, 2013, https://doi.org/10.1080/10406638.2019.1584575