Copyright (c) 2014 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Some Biologically Active Pyrazolylphthalazine Derivatives and Acyclo-C-nucleosides of 6-(2,4,6-trimethylphenyl)-1,2,4-triazolo[3,4-a]phthalazine
Corresponding Author(s) : Ibrahim E. El-Shamy
Asian Journal of Chemistry,
Vol. 26 No. 14 (2014): Vol 26 Issue 14
Abstract
1-Chloro-4-(2,4,6-trimethylphenyl)phthalazine (2) was used as a precursor for preparation of some novel pyrazolylphthalazine derivatives 6-13 and 15-19. Moreover, the acyclonucleosides 20-23 a-e were prepared by the reaction of hydrazinophthalazine derivative 3 with different aldoses. All new phthalazine derivatives were characterized using 1H NMR, 13C NMR, FTIR, mass spectrum and elemental analysis. The newly synthesized compounds showed highly activity against different species of bacteria and fungi, in addition to an excellent antiinflammatory property.
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- M.S. Chorghade, Drug Discovery and Development; John Wiley & Sons: Hoboken, New Jersey, Vol. 2 (2007).
- D. Lednicer and L.A. Mitscher, The Organic Chemistry of Drug Synthesis; John Wiley & Sons: New York, Chichester, Brisbane, Toronto, Vol. 1 (1977).
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- G. Strappaghetti, C. Brodi, G. Giannaccini and L. Betti, Bioorg. Med. Chem. Lett., 16, 2575 (2006).
- A.D. Lebsack, J. Gunzner, B. Wang, R. Pracitto, H. Schaffhauser, A. Santini, J. Aiyar, R. Bezverkov, B. Munoz, W. Liu and S. Venkatraman, Bioorg. Med. Chem. Lett., 14, 2463 (2004).
- T. Haack, R. Fattori, M. Napoletano, F. Pellacini, G. Fronza, G. Raffaini and F. Ganazzoli, Bioorg. Med. Chem., 13, 4425 (2005).
- E.L. Piatnitski, M.A.J. Duncton, A.S. Kiselyov, R. Katoch-Rouse, D. Sherman, D.L. Milligan, C. Balagtas, W.C. Wong, J. Kawakami and J.F. Doody, Bioorg. Med. Chem. Lett., 15, 4696 (2005).
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- A. Hamed, E.R. Abo-Amaym and E.H. El-Ashry, Nucleosides Nucleotides, 17, 1385 (1998).
- L.F. Awad and E.S.H.E. Ashry, Carbohydr. Res., 312, 9 (1998).
- C. Turk, J. Svete, A. Golobic, L. Golic and B. Stanovnik, J. Heterocycl. Chem., 35, 513 (1998).
- M.A.E. Shaban and A.Z. Nasr, Adv. Heterocycl. Chem., 68, 223 (1997).
- M.A.E. Shaban and A.E.A. Morgaan, Adv. Heterocycl. Chem., 73, 131 (1999).
- E.S.H. El-Ashry and Y. El-Kilany, Adv. Heterocycl. Chem., 69, 129 (1997).
- M.A. El-Hashash, A.Y. Soliman and I.E. El-Shamy, Turk. J. Chem., 36, 347 (2012).
- C.W. Thornber, J.M. Farrell and D.S. Clarke, Synthesis, 222 (1983).
- S.M. Fahmy and R.M. Mohareb, Liebigs Ann. Chem., 1492 (1985).
- M. Ishii, M. Iwahana, I. Mitsui, M. Minami, S. Imagawa, A. Tohgo and A. Ejima, Anticancer Drugs, 11, 353 (2000).
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- B.D. Robert and W. Robin, Eur. Patent, 2,895 (1979); Chem. Abstr., 92, 76533v (1980).
- M. Van der Mey, A. Hatzelmann, G.P.M. Van Klink, I.J. Van der Laan, G.J. Sterk, U. Thibaut, W.R. Ulrich and H. Timmerman, J. Med. Chem., 44, 2523 (2001).
- W.O. Foye, Principle of Medicinal Chemistry, Philadeliphia, London, edn. 3, p. 516 (1989).
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- T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert,A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997).
- C.A. Winter, E.A. Risley and G.W. Nuss, Proc. Soc. Exp. Biol. Med., 111, 544 (1962).
- M.A. El-Hashash, A.Y. El-Kady, M.A. Taha and I.E. El-Shamy, Chinese J. Chem., 30, 616 (2012).
- I.E. El-Shamy, H.M. Bakeer, K.M. Al-Shamrani, A.M. Abdel-Mohsen and M.M. Al-Shehri, Life Sci. J., 11, 94 (2014).
References
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D. Lednicer and L.A. Mitscher, The Organic Chemistry of Drug Synthesis; John Wiley & Sons: New York, Chichester, Brisbane, Toronto, Vol. 1 (1977).
F. Al-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan and B.A. Chakchir, Pharm. Chem. J., 36, 598 (2002).
R.W. Carling, K.W. Moore, L.J. Street, D. Wild, C. Isted, P.D. Leeson, S. Thomas, D. O'Connor, R.M. McKernan, K. Quirk, S.M. Cook, J.R. Atack, K.A. Wafford, S.A. Thompson, G.R. Dawson, P. Ferris and J.L. Castro, J. Med. Chem., 47, 1807 (2004).
R.P. Jain and J.C. Vederas, Bioorg. Med. Chem. Lett., 14, 3655 (2004).
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).
G. Strappaghetti, C. Brodi, G. Giannaccini and L. Betti, Bioorg. Med. Chem. Lett., 16, 2575 (2006).
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E.L. Piatnitski, M.A.J. Duncton, A.S. Kiselyov, R. Katoch-Rouse, D. Sherman, D.L. Milligan, C. Balagtas, W.C. Wong, J. Kawakami and J.F. Doody, Bioorg. Med. Chem. Lett., 15, 4696 (2005).
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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).
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M.C. Cardia, S. Distinto, E. Maccioni, L. Bonsignore and A. Delogu, J. Heterocycl. Chem., 40, 1011 (2003).
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A.Z. Haikal, E.S.H. El Ashry and J. Banoub, Carbohydr. Res., 338, 2291 (2003).
S. Demirayak, A. Karaburun and R. Beis, Eur. J. Med. Chem., 39, 1089 (2004).
N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama and H. Adachi, J. Med. Chem., 41, 3367 (1998).
M. Johnsen, K. Rehse, H. Pertz, J.P. Stasch and E. Bischoff, Arch. Pharmacol., 336, 591 (2003).
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D.S. Dogruer, E. Kupeli, E. Yesilada and M.F. Sahin, Arch. Pharmcol., 337, 303 (2004).
M. Napoletano, G. Norcini, F. Pellacini, F. Marchini, G. Morazzoni, P. Ferlenga and L. Pradella, Bioorg. Med. Chem. Lett., 10, 2235 (2000).
A.K. Chakraborti, B. Gopalakrishnan, E. Sobhia and A. Malde, Bioorg. Med. Chem. Lett., 13, 2473 (2003).
M. Van der Mey, A. Hatzelmann, I.J. van der Laan, G.J. Sterk, U. Thibaut and H. Timmerman, J. Med. Chem., 44, 2511 (2001).
M. Van der Mey, H. Boss, D. Couwenberg, A. Hatzelmann, G.J. Sterk, K. Goubitz, H. Schenk and H. Timmerman, J. Med. Chem., 45, 2526 (2002).
K.M. Shubin, V.A. Kuznetsov and V.A. Galishev, Tetrahedron Lett., 45, 1407 (2004).
B. Herberich, G.-Q. Cao, P.P. Chakrabarti, J.R. Falsey, L. Pettus, R.M. Rzasa, A.B. Reed, A. Reichelt, K. Sham, M. Thaman, R.P. Wurz, S. Xu, D. Zhang, F. Hsieh, M.R. Lee, R. Syed, V. Li, D. Grosfeld, M.H. Plant, B. Henkle, L. Sherman, S. Middleton, L.M. Wong and A.S. Tasker, J. Med. Chem., 51, 6271 (2008).
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).
J.R. Cashman, T. Voelker, R. Johnson and A. Janowsky, Bioorg. Med. Chem., 17, 337 (2009).
T. Sheradsky and R. Moshenberg, J. Org. Chem., 51, 3123 (1986).
H.W. Heine, L.M. Baclawski, S.M. Bonser and G.D. Wachob, J. Org. Chem., 41, 3229 (1976).
Y.K. Ramtohul, M.N.G. James and J.C. Vederas, J. Org. Chem., 67, 3169 (2002).
L.P. Liu, J.M. Lu and M. Shi, Org. Lett., 9, 1303 (2007).
A. CsXmpai, K. Körmendy and F. Ruff, Tetrahedron, 47, 4457 (1991).
A.S. Amarasekara and S. Chandrasekara, Org. Lett., 4, 773 (2002).
J.Y. Hwang, H.-S. Choi and Y.-D. Gong, Tetrahedron Lett., 46, 3107 (2005).
R.J. Shuhadolink, C-Nucleosides Antibiotics, Wiley Interscience, New York (1970).
E.S. H. El Ashry, N. Rashed and A. Mousaad, J. Carbohydr. Chem., 6, 599 (1987).
G.A. El-Hiti, Alex. J. Pharm. Sci., 14, 37 (2000).
Y.A. Alsoud and N.A. Almasoudi, Arch. Pharm., 332, 143 (1999).
A. Hamed, E.R. Abo-Amaym and E.H. El-Ashry, Nucleosides Nucleotides, 17, 1385 (1998).
L.F. Awad and E.S.H.E. Ashry, Carbohydr. Res., 312, 9 (1998).
C. Turk, J. Svete, A. Golobic, L. Golic and B. Stanovnik, J. Heterocycl. Chem., 35, 513 (1998).
M.A.E. Shaban and A.Z. Nasr, Adv. Heterocycl. Chem., 68, 223 (1997).
M.A.E. Shaban and A.E.A. Morgaan, Adv. Heterocycl. Chem., 73, 131 (1999).
E.S.H. El-Ashry and Y. El-Kilany, Adv. Heterocycl. Chem., 69, 129 (1997).
M.A. El-Hashash, A.Y. Soliman and I.E. El-Shamy, Turk. J. Chem., 36, 347 (2012).
C.W. Thornber, J.M. Farrell and D.S. Clarke, Synthesis, 222 (1983).
S.M. Fahmy and R.M. Mohareb, Liebigs Ann. Chem., 1492 (1985).
M. Ishii, M. Iwahana, I. Mitsui, M. Minami, S. Imagawa, A. Tohgo and A. Ejima, Anticancer Drugs, 11, 353 (2000).
R. Noto, F. Buccheri, G. Cusmano, M. Gruttadauria and G. Werber, J. Heterocycl. Chem., 28, 1421 (1991).
B.D. Robert and W. Robin, Eur. Patent, 2,895 (1979); Chem. Abstr., 92, 76533v (1980).
M. Van der Mey, A. Hatzelmann, G.P.M. Van Klink, I.J. Van der Laan, G.J. Sterk, U. Thibaut, W.R. Ulrich and H. Timmerman, J. Med. Chem., 44, 2523 (2001).
W.O. Foye, Principle of Medicinal Chemistry, Philadeliphia, London, edn. 3, p. 516 (1989).
W.O. Foye, T.L. Lemke and D.A. Williams, Principle of Medicinal Chemistry, A Waverly Company, edn. 4, p. 554 (1989).
T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert,A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997).
C.A. Winter, E.A. Risley and G.W. Nuss, Proc. Soc. Exp. Biol. Med., 111, 544 (1962).
M.A. El-Hashash, A.Y. El-Kady, M.A. Taha and I.E. El-Shamy, Chinese J. Chem., 30, 616 (2012).
I.E. El-Shamy, H.M. Bakeer, K.M. Al-Shamrani, A.M. Abdel-Mohsen and M.M. Al-Shehri, Life Sci. J., 11, 94 (2014).