Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Antimicrobial Evaluation of Some New 2-(5,6-Dihydro-4H-1,2,4-triazolo[4,3-a]benz[F]azepin-1-yl)methyl)-4-substituted Phthalazin-1(2H)-ones
Corresponding Author(s) : Ibrahim E. El-Shamy
Asian Journal of Chemistry,
Vol. 26 No. 22 (2014): Vol 26 Issue 22
Abstract
Starting from 4-substituted-phthalazin-1(2H)-one (1), A series of new 2-(5,6-dihydro-4H-1,2,4-triazolo[4,3-a]benz[f]azepin-1-yl)methyl)-4-substituted phthalazin-1(2H)-ones derivatives (5) have been synthesized. The structure of synthesized new compounds was established by spectral data and screened for their antimicrobial activities against various bacteria and fungi strains.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- (a) E.C. Franklin, Chem. Rev., 16, 305 (1935); doi:10.1021/cr60055a001; (b) F.W. Bergstrom, Chem. Rev., 35, 77 (1944); doi:10.1021/cr60111a001; (c) F.W. Lichtenthaler, Acc. Chem. Res., 35, 728 (2002); doi:10.1021/ar010071i; (d) V.P. Litvinov, Russ. Chem. Rev., 72, 69 (2003); doi:10.1070/RC2003v072n01ABEH000764; (e) Q.-X. Guo and Y. Xu, Heterocycles, 63, 903 (2004); doi:10.3987/REV-03-574.
- B. Abd El-Fattah, M.I. Al-Ashmawi, S. El-Feky and E. Roder, Egypt. J. Pharm. Sci., 29, 259 (1988).
- B.E. Bayoumy, S.A. El-Feky and M. El-Mobayed, Egypt. J. Chem., 33, 267 (1991).
- M.A. Khalil, S.M. El-Khawss and M.G. Kassem, Sci. Pharm., 48, 344 (1980).
- O.M. Boland, C.C. Blackwell, B.F. Clarke and D.J. Ewing, Diabetes, 42, 336 (1993); doi:10.2337/diab.42.2.336.
- Y. Hamamoto, K. Nagai, M. Muto and C. Asagami, Exp. Dermatol., 2, 231 (1993); doi:10.1111/j.1600-0625.1993.tb00038.x.
- E. Olmo, B. Barboza, M.I. Ybarra, J.L. López-Pérez, R. Carrón, M.A. Sevilla, C. Boselli and A.S. Feliciano, Bioorg. Med. Chem. Lett., 16, 2786 (2006); doi:10.1016/j.bmcl.2006.02.003.
- M. Napoletano, G. Norcini, F. Pellacini, F. Marchini, G. Morazzoni, P. Ferlenga and L. Pradella, Bioorg. Med. Chem. Lett., 10, 2235 (2000); doi:10.1016/S0960-894X(00)00449-2.
- G. Bold, K.-H. Altmann, J. Frei, M. Lang, P.W. Manley, P. Traxler, B. Wietfeld, J. Brüggen, E. Buchdunger, R. Cozens, S. Ferrari, P. Furet, F. Hofmann, G. Martiny-Baron, J. Mestan, J. Rösel, M. Sills, D. Stover, F. Acemoglu, E. Boss, R. Emmenegger, L. Lässer, E. Masso, R. Roth, C. Schlachter, W. Vetterli, D. Wyss and J.M. Wood, J. Med. Chem., 43, 2310 (2000); doi:10.1021/jm9909443.
- J.M. Arif, M. Kunhi, A.A. Bekhit, M.P. Subramanian and K. Al-Hussein, H.Y. Aboul-Enein Fahad and M. Al-Khodairy, Asian Pac. J. Cancer Prev., 7, 249 (2006).
- M. Yamaguchi, K. Kamei, T. Koga, M. Akima, T. Kuroki and N. Ohi, J. Med. Chem., 36, 4052 (1993); doi:10.1021/jm00077a008.
- Y.X. Li, Y.P. Luo, Z. Xi, C.W. Niu, Y.Z. He and G.F. Yang, J. Agric. Food Chem., 54, 9135 (2006); doi:10.1021/jf061976j.
- F.H.H. Leenen, D.L. Smith, R.M. Farkas, R.A. Reeves and A. Marquez-Julio, Am. J. Med., 82, 969 (1987); doi:10.1016/0002-9343(87)90160-4.
- J.M. Leiro, E. Alvarez, J.A. Arranz, E. Cano and F. Orallo, Int. Immunopharmacol., 4, 163 (2004); doi:10.1016/j.intimp.2003.10.004.
- S. Tanaka, M. Tanaka and A. Akashi, Stroke, 20, 1724 (1989); doi:10.1161/01.STR.20.12.1724.
- R. Moroi, K. Ono, T. Saito, T. Akimoto and M. Sano, Chem. Pharm. Bull. (Tokyo), 25, 830 (1977); doi:10.1248/cpb.25.830.
- J.P. Kemp, E.O. Meltzer, H.A. Orgel, M.J. Welch, G.A. Bucholtz, E. Middleton Jr., S.L. Spector, J.J. Newton and J.L. Perhach Jr., J. Allergy Clin. Immunol., 79, 893 (1987); doi:10.1016/0091-6749(87)90238-7.
- G. Scheffler, J. Engel, B. Kutscher, W.S. Sheldrick and P. Bell, Arch. Pharmazie, 321, 205 (1988); doi:10.1002/ardp.19883210406.
- P.F. Kador, J.H. Kinoshita and N.E. Sharpless, J. Med. Chem., 28, 841 (1985); doi:10.1021/jm00145a001.
- B.L. Mylari, E.R. Larson, T.A. Beyer, W.J. Zembrowski, C.E. Aldinger, M.F. Dee, T.W. Siegel and D.H. Singleton, J. Med. Chem., 34, 108 (1991); doi:10.1021/jm00105a018.
- S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappalà, G. Puja, M. Baraldi and C. De Micheli, J. Med. Chem., 43, 2851 (2000); doi:10.1021/jm001002x.
- D. Viña, E. del Olmo, J.L. Lopez-Pérez and A. San Feliciano, Tetrahedron, 65, 1574 (2009); doi:10.1016/j.tet.2008.12.072.
- F.F. Blicke and R.D. Swisher, J. Am. Chem. Soc., 56, 923 (1934); doi:10.1021/ja01319a047.
- E. Olmo, B. Barboza, M.I. Ybarra, J.L. López-Pérez, R. Carrón, M.A. Sevilla, C. Boselli and A.S. Feliciano, Bioorg. Med. Chem. Lett., 16, 2786 (2006); doi:10.1016/j.bmcl.2006.02.003.
References
(a) E.C. Franklin, Chem. Rev., 16, 305 (1935); doi:10.1021/cr60055a001; (b) F.W. Bergstrom, Chem. Rev., 35, 77 (1944); doi:10.1021/cr60111a001; (c) F.W. Lichtenthaler, Acc. Chem. Res., 35, 728 (2002); doi:10.1021/ar010071i; (d) V.P. Litvinov, Russ. Chem. Rev., 72, 69 (2003); doi:10.1070/RC2003v072n01ABEH000764; (e) Q.-X. Guo and Y. Xu, Heterocycles, 63, 903 (2004); doi:10.3987/REV-03-574.
B. Abd El-Fattah, M.I. Al-Ashmawi, S. El-Feky and E. Roder, Egypt. J. Pharm. Sci., 29, 259 (1988).
B.E. Bayoumy, S.A. El-Feky and M. El-Mobayed, Egypt. J. Chem., 33, 267 (1991).
M.A. Khalil, S.M. El-Khawss and M.G. Kassem, Sci. Pharm., 48, 344 (1980).
O.M. Boland, C.C. Blackwell, B.F. Clarke and D.J. Ewing, Diabetes, 42, 336 (1993); doi:10.2337/diab.42.2.336.
Y. Hamamoto, K. Nagai, M. Muto and C. Asagami, Exp. Dermatol., 2, 231 (1993); doi:10.1111/j.1600-0625.1993.tb00038.x.
E. Olmo, B. Barboza, M.I. Ybarra, J.L. López-Pérez, R. Carrón, M.A. Sevilla, C. Boselli and A.S. Feliciano, Bioorg. Med. Chem. Lett., 16, 2786 (2006); doi:10.1016/j.bmcl.2006.02.003.
M. Napoletano, G. Norcini, F. Pellacini, F. Marchini, G. Morazzoni, P. Ferlenga and L. Pradella, Bioorg. Med. Chem. Lett., 10, 2235 (2000); doi:10.1016/S0960-894X(00)00449-2.
G. Bold, K.-H. Altmann, J. Frei, M. Lang, P.W. Manley, P. Traxler, B. Wietfeld, J. Brüggen, E. Buchdunger, R. Cozens, S. Ferrari, P. Furet, F. Hofmann, G. Martiny-Baron, J. Mestan, J. Rösel, M. Sills, D. Stover, F. Acemoglu, E. Boss, R. Emmenegger, L. Lässer, E. Masso, R. Roth, C. Schlachter, W. Vetterli, D. Wyss and J.M. Wood, J. Med. Chem., 43, 2310 (2000); doi:10.1021/jm9909443.
J.M. Arif, M. Kunhi, A.A. Bekhit, M.P. Subramanian and K. Al-Hussein, H.Y. Aboul-Enein Fahad and M. Al-Khodairy, Asian Pac. J. Cancer Prev., 7, 249 (2006).
M. Yamaguchi, K. Kamei, T. Koga, M. Akima, T. Kuroki and N. Ohi, J. Med. Chem., 36, 4052 (1993); doi:10.1021/jm00077a008.
Y.X. Li, Y.P. Luo, Z. Xi, C.W. Niu, Y.Z. He and G.F. Yang, J. Agric. Food Chem., 54, 9135 (2006); doi:10.1021/jf061976j.
F.H.H. Leenen, D.L. Smith, R.M. Farkas, R.A. Reeves and A. Marquez-Julio, Am. J. Med., 82, 969 (1987); doi:10.1016/0002-9343(87)90160-4.
J.M. Leiro, E. Alvarez, J.A. Arranz, E. Cano and F. Orallo, Int. Immunopharmacol., 4, 163 (2004); doi:10.1016/j.intimp.2003.10.004.
S. Tanaka, M. Tanaka and A. Akashi, Stroke, 20, 1724 (1989); doi:10.1161/01.STR.20.12.1724.
R. Moroi, K. Ono, T. Saito, T. Akimoto and M. Sano, Chem. Pharm. Bull. (Tokyo), 25, 830 (1977); doi:10.1248/cpb.25.830.
J.P. Kemp, E.O. Meltzer, H.A. Orgel, M.J. Welch, G.A. Bucholtz, E. Middleton Jr., S.L. Spector, J.J. Newton and J.L. Perhach Jr., J. Allergy Clin. Immunol., 79, 893 (1987); doi:10.1016/0091-6749(87)90238-7.
G. Scheffler, J. Engel, B. Kutscher, W.S. Sheldrick and P. Bell, Arch. Pharmazie, 321, 205 (1988); doi:10.1002/ardp.19883210406.
P.F. Kador, J.H. Kinoshita and N.E. Sharpless, J. Med. Chem., 28, 841 (1985); doi:10.1021/jm00145a001.
B.L. Mylari, E.R. Larson, T.A. Beyer, W.J. Zembrowski, C.E. Aldinger, M.F. Dee, T.W. Siegel and D.H. Singleton, J. Med. Chem., 34, 108 (1991); doi:10.1021/jm00105a018.
S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappalà, G. Puja, M. Baraldi and C. De Micheli, J. Med. Chem., 43, 2851 (2000); doi:10.1021/jm001002x.
D. Viña, E. del Olmo, J.L. Lopez-Pérez and A. San Feliciano, Tetrahedron, 65, 1574 (2009); doi:10.1016/j.tet.2008.12.072.
F.F. Blicke and R.D. Swisher, J. Am. Chem. Soc., 56, 923 (1934); doi:10.1021/ja01319a047.
E. Olmo, B. Barboza, M.I. Ybarra, J.L. López-Pérez, R. Carrón, M.A. Sevilla, C. Boselli and A.S. Feliciano, Bioorg. Med. Chem. Lett., 16, 2786 (2006); doi:10.1016/j.bmcl.2006.02.003.