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Synthesis of Some Novel Thiobarbituric Acid Derivatives and Their Related Compounds from Sulfa-Drug as Antiinflammatory
Corresponding Author(s) : Mohie Aldin M. Zayed
Asian Journal of Chemistry,
Vol. 26 No. 3 (2014): Vol 26 Issue 3
Abstract
In search for new antiinflammatory agents, some new substituted thiobarbituric acids (2) and their bis-fused or fused thiopyrimidinyl-pyrimidinone (7, 8) have been derived from sulfathiazole and dimethylmalonate with CS2. structures of the synthesized compounds were established by spectroscopic (FT-IR, 1H NMR, 13C NMR, Mass) and elemental analyses. The antiinflammatory activity of these compounds was tested against carrageen-induced oedema with the reference of standard drug phenyl butazone. The results showed that compounds 2 and 3 are better antiinflammatory agents as compared to standard drug phenyl butazone.
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- A. De Logu, V. Omis, B. Saddi, C. Congien and M.L. Schivo, J. Antimicrob. Chemother., 49, 275 (2002); doi:10.1093/jac/49.2.275.
- L. Savini, L. Chiasserini, A. Gaeta and C. Pellerano, Bioorg. Med. Chem., 10, 2193 (2002); doi:10.1016/S0968-0896(02)00071-8.
- A.M. Asiri and S.A. Khan, Molecules, 15, 4784 (2010); doi:10.3390/molecules15074784.
- A. Andreani, M. Granaiola, A. Lemi, A. Locatelli, R. Morigi, M. Rambaldi, G. Giorgi and V. Garaliene, Anticancer Res., 24, 203 (2004).
- M.E. Furrow and A.G. Myers, J. Am. Chem. Soc., 126, 436 (2004); doi: 10.1021/ja049694s .
- S.A. Khan, N. Singh and K. Saleem, Eur. J. Med. Chem., 43, 2272 (2008); doi:10.1016/j.ejmech.2007.12.012.
- G.R. Cook, B.C. Maity and R. Kargbo, Org. Lett., 6, 1741 (2004); doi:10.1021/ol0496172.
- A.K. Halve, P. Gour, R. Dubey, D. Bhadauria and B. Bhaskari, J. Indian Chem. Soc., 82, 942 (2005).
- A.M. Asiri and S.A. Khan, Molecules, 16, 523 (2011); doi:10.3390/molecules16010523.
- R.M. Abdel-Rahman, J.M. Morsy, F. Hanafy and H.A. Amene, Pharmazie, 54, 347 (1999).
- R.M. Abdel-Rahman, Pharmazie, 56, 18 (2001).
- R.M. Abdel-Rahman, Pharmazie, 56, 195 (2001).
- R.M. Abdel-Rahman, Trends Heterocycl. Chem., 8, 187 (2002).
- W.R. Abdel-Monem and R.M. Abdel-Rahman, Int. J. Chem., 16, 1 (2006).
- M.A. Ibrahim, R.M. Abdel-Rahman, A.M. Abdel-Halim, S.S. Ibrahim and H.A. Allimony, ARKIVOC, 202 (2008); doi:10.3998/ark.5550190.0009.g19.
- M.G. Valverde and T. Torroba, Sulfur-Nitrogen Heterocycl. Mol., 10, 318 (2005).
- S.M. Abu-El-Wafa, R.M. Abdel-Rahman and Z. El-Gendy, Egypt. J. Chem., 33, 387 (1990).
- J.H. Chern, K.S. Shia, C.M. Chang, C.C. Lee, Y.-C. Lee, C.-L. Tai, Y.-T. Lin, C.-S. Chang and H.-Y. Tseng, Bioorg. Med. Chem. Lett., 14, 1169 (2004); doi:10.1016/j.bmcl.2003.12.073.
- M. Seada, R.M. Abdel-Rahman and M. Abdel-Megib, Indian J. Heterocycl. Chem., 3, 9 (1993).
- T.E. Ali, R.M. Abdel-Rahman, F.I. Hanafy and S.M. El-Edfawy, Phosphorus Sulfur Silicon Rel. Elem., 183, 2577 (2008);doi:10.1080/10426500801967864.
- M.A. Ibrahim, R.M. Abdel-Rahman, A.M. Abdel-Halim, S.S. Ibrahim and H.A. Allimony, J. Braz. Chem. Soc., 20, 1275 (2009); doi:10.1590/S0103-50532009000700012.
- C.A. Winter, E.A. Risley and G.W. Nuss, Exp. Biol. Med., 111, 544 (1962); doi:10.3181/00379727-111-27849.
- P. Ashokkumar and G. Sudhandiran, Biomed. Pharmacother., 62, 590 (2008); doi:10.1016/j.biopha.2008.06.031.
- C.A. Winter, E.A. Risley and G.W. Nuss, J. Pharmacol. Exp. Ther., 141, 369 (1963).
- R.M. Abdel-Rahman, M.S.T. Makki and W.A. Bawazir, E.-J. Chem., 7, 93 (2010); doi:10.1155/2010/467564.
- R.M. Abdel-Rahman, M.S.T. Makki and W.A. Bawazir, E.-J. Chem., 8, 405 (2011); doi:10.1155/2011/586063.
- R.M. Abdel-Rahman, K.O. Al-Footy and F.M. Aglan, Int. J. Chem. Tech. Res., 3, 423 (2011).
References
A. De Logu, V. Omis, B. Saddi, C. Congien and M.L. Schivo, J. Antimicrob. Chemother., 49, 275 (2002); doi:10.1093/jac/49.2.275.
L. Savini, L. Chiasserini, A. Gaeta and C. Pellerano, Bioorg. Med. Chem., 10, 2193 (2002); doi:10.1016/S0968-0896(02)00071-8.
A.M. Asiri and S.A. Khan, Molecules, 15, 4784 (2010); doi:10.3390/molecules15074784.
A. Andreani, M. Granaiola, A. Lemi, A. Locatelli, R. Morigi, M. Rambaldi, G. Giorgi and V. Garaliene, Anticancer Res., 24, 203 (2004).
M.E. Furrow and A.G. Myers, J. Am. Chem. Soc., 126, 436 (2004); doi: 10.1021/ja049694s .
S.A. Khan, N. Singh and K. Saleem, Eur. J. Med. Chem., 43, 2272 (2008); doi:10.1016/j.ejmech.2007.12.012.
G.R. Cook, B.C. Maity and R. Kargbo, Org. Lett., 6, 1741 (2004); doi:10.1021/ol0496172.
A.K. Halve, P. Gour, R. Dubey, D. Bhadauria and B. Bhaskari, J. Indian Chem. Soc., 82, 942 (2005).
A.M. Asiri and S.A. Khan, Molecules, 16, 523 (2011); doi:10.3390/molecules16010523.
R.M. Abdel-Rahman, J.M. Morsy, F. Hanafy and H.A. Amene, Pharmazie, 54, 347 (1999).
R.M. Abdel-Rahman, Pharmazie, 56, 18 (2001).
R.M. Abdel-Rahman, Pharmazie, 56, 195 (2001).
R.M. Abdel-Rahman, Trends Heterocycl. Chem., 8, 187 (2002).
W.R. Abdel-Monem and R.M. Abdel-Rahman, Int. J. Chem., 16, 1 (2006).
M.A. Ibrahim, R.M. Abdel-Rahman, A.M. Abdel-Halim, S.S. Ibrahim and H.A. Allimony, ARKIVOC, 202 (2008); doi:10.3998/ark.5550190.0009.g19.
M.G. Valverde and T. Torroba, Sulfur-Nitrogen Heterocycl. Mol., 10, 318 (2005).
S.M. Abu-El-Wafa, R.M. Abdel-Rahman and Z. El-Gendy, Egypt. J. Chem., 33, 387 (1990).
J.H. Chern, K.S. Shia, C.M. Chang, C.C. Lee, Y.-C. Lee, C.-L. Tai, Y.-T. Lin, C.-S. Chang and H.-Y. Tseng, Bioorg. Med. Chem. Lett., 14, 1169 (2004); doi:10.1016/j.bmcl.2003.12.073.
M. Seada, R.M. Abdel-Rahman and M. Abdel-Megib, Indian J. Heterocycl. Chem., 3, 9 (1993).
T.E. Ali, R.M. Abdel-Rahman, F.I. Hanafy and S.M. El-Edfawy, Phosphorus Sulfur Silicon Rel. Elem., 183, 2577 (2008);doi:10.1080/10426500801967864.
M.A. Ibrahim, R.M. Abdel-Rahman, A.M. Abdel-Halim, S.S. Ibrahim and H.A. Allimony, J. Braz. Chem. Soc., 20, 1275 (2009); doi:10.1590/S0103-50532009000700012.
C.A. Winter, E.A. Risley and G.W. Nuss, Exp. Biol. Med., 111, 544 (1962); doi:10.3181/00379727-111-27849.
P. Ashokkumar and G. Sudhandiran, Biomed. Pharmacother., 62, 590 (2008); doi:10.1016/j.biopha.2008.06.031.
C.A. Winter, E.A. Risley and G.W. Nuss, J. Pharmacol. Exp. Ther., 141, 369 (1963).
R.M. Abdel-Rahman, M.S.T. Makki and W.A. Bawazir, E.-J. Chem., 7, 93 (2010); doi:10.1155/2010/467564.
R.M. Abdel-Rahman, M.S.T. Makki and W.A. Bawazir, E.-J. Chem., 8, 405 (2011); doi:10.1155/2011/586063.
R.M. Abdel-Rahman, K.O. Al-Footy and F.M. Aglan, Int. J. Chem. Tech. Res., 3, 423 (2011).