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Synthesis, Characterization and Thermal Analysis for New Amoxil Ligands
Corresponding Author(s) : Nagham Mahmood Aljamali
Asian Journal of Chemistry,
Vol. 31 No. 5 (2019): Vol 31 Issue 5
Abstract
In the present study, new heterocyclic organic ligands were synthesized using amoxil drug as a starting material through multi steps. The ligands were prepared through condensation reaction to form thiazole and imidazole derivatives containing azo or anil groups in their structures via azotization reaction and imination reaction. The new ligands of amoxil have been characterized by means of spectral (IR and 1H NMR) and thermal analyses.
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- W.A. Al Masoudi, H.T. Mohammad and A.A. Hama, Int. Res. J. Pharm., 6, 386 (2015); https://doi.org/10.7897/2230-8407.06680.
- D.A. Kummer, D. Li, A. Dion and A.G. Myers, Chem. Sci., 2, 1710 (2011); https://doi.org/10.1039/c1sc00303h.
- M.G. Charest, C.D. Lerner, J.D. Brubaker, D. Siegel and A.G. Myers, Science, 308, 395 (2005); https://doi.org/10.1126/science.1109755.
- C. Sun, Q. Wang, J.D. Brubaker, P. Wright, C.D. Lerner, K. Noson, M. Charest, D.R. Siegel, Y.-M. Wang and A.G. Myers, J. Am. Chem. Soc., 130, 17913 (2008); https://doi.org/10.1021/ja806629e.
- K.C. Nicolaou, C. Nilewski, C.R.H. Hale, H.A. Ioannidou, A. ElMarrouni and L.G. Koch, Angew. Chem. Int. Ed., 52, 8736 (2013); https://doi.org/10.1002/anie.201304691.
- Y.F. Baba, H. Elmsellem, Y.K. Rodi, H. Steli, C. Ad, Y. Ouzidan, F.O. Chahdi, N.K. Sebbar, E.M. Essassi and B. Hammouti, Der Pharma Chemica, 8, 159 (2016).
- K.M. Kulkarni, S.A. Jadhav, P.B. Patil, V.R. Dhole and S.S. Patil, Der Pharma Chemica, 8, 38 (2016).
- S.-J. Chao, X.-P. Hui, S. Li, Z.-Z. Qiu, P.-F. Xu, Z.-Y. Zhang, Q. Wang and Z.-W. Guan, J. Chin. Chem. Soc., 52, 539 (2005); https://doi.org/10.1002/jccs.200500079.
- Ö. Ates, A. Kocabalkanli, N. Cesur and G. Ötük, Farmaco, 53, 541 (1998); https://doi.org/10.1016/S0014-827X(98)00063-9.
- C.A.G.N. Montalbetti and V. Falque, Tetrahedron, 61, 10827 (2005); https://doi.org/10.1016/j.tet.2005.08.031.
- N.M. Aljamali, Pak. J. Biotechnol., 15, 219 (2018).
- S.N. Swamy, Basappa, B.S. Priya, B. Prabhuswamy, B.H. Doreswamy, J.S. Prasad and K.S. Rangappa, Eur. J. Med. Chem., 41, 531 (2006); https://doi.org/10.1016/j.ejmech.2005.12.009.
- L. Jin, J. Chen, B. Song, Z. Chen, S. Yang, Q. Li, D. Hu and R. Xu, Bioorg. Med. Chem. Lett., 16, 5036 (2006); https://doi.org/10.1016/j.bmcl.2006.07.048.
- M. Mohammed, N.M. Aljamali and N.A. Abbas, J. Global Pharm. Technol., 10, 20 (2018).
- F.J. Uribe-Romo, J.R. Hunt, H. Furukawa, C. Klock, M. O’Keeffe and O.M. Yaghi, J. Am. Chem. Soc., 131, 4570 (2009); https://doi.org/10.1021/ja8096256.
- N.M. Aljamali and I.O. Alfatlawi, Res. J. Pharm. Technol., 8, 1225 (2015); https://doi.org/10.5958/0974-360X.2015.00224.3.
- M. Mohammed, N.M. Aljamali, S.A. Abdalrahman and W.A. Shubber, Biochem. Cell. Arch., 18, 847 (2018).
- J.C. Hindson, B. Ulgut, R.H. Friend, N.C. Greenham, B. Norder, A. Kotlewski and T.J. Dingemans, J. Mater. Chem., 20, 937 (2010); https://doi.org/10.1039/B919159C.
- R.J. Cremlyn, An Introduction to Organosulfur Chemistry, John Wiley & Sons: Chichester (1996).
- N.M. Aljamali, S.M. Jawd, Z.M. Jawad and I.O. Alfatlawi, Res. J. Pharm. Technol., 10, 1683 (2017); https://doi.org/10.5958/0974-360X.2017.00297.9.
- J. Drabowicz, J. Lewkowski, W. Kudelska and T. Girek, ed.: N. Kamble, S,S-Dialkylsulfoximides, In: Science of Synthesis, Thieme, vol. 39, pp. 154-173 (2008).
- J. Drabowicz, J. Lewkowski, W. Kudelska and T. Girek, ed.: N. Kamble, S,S-Dialkylsulfonediimines, In: Science of Synthesis, Thieme, vol. 39, pp. 173–180 (2008).
- Y. Zhang and N. Hogg, Free Radic. Biol. Med., 38, 831 (2005); https://doi.org/10.1016/j.freeradbiomed.2004.12.016.
- S. Braverman, M. Cherkinsky and S. Levinger, ed.: N. Kamble, Alkylsulfur Trihalides, In: Science of Synthesis, Thieme, vol. 39, pp. 187-188 (2008).
- J. Drabowicz, J. Lewkowski, W. Kudelska and T. Girek, ed.: N. Kamble, Dialkylsulfur Tetrahalides, In: Science of Synthesis, Thieme, vol. 39, pp. 123-124 (2008).
- P. Arora, V. Arora, H.S. Lamba and D. Wadhwa, Int. J. Pharm. Res. Sci., 3, 2947 (2012).
- N.M. Aljamali and D. Rahi, J. Chem. Pharm. Sci., 10, 1461 (2017).
- H.S. Eman and N.M. Aljamali, J. Global Pharma Technol., 11, 165 (2017).
- N.M. Aljamali, Reactions and Mechanisms, IJMRA Publication: Germany, edn 1 (2018).
- I. Schneider, E. Keuleyan, R. Rasshofer, R. Markovska, A.M. Queenan and A. Bauernfeind, Antimicrob. Agents Chemother., 52, 2977 (2008); https://doi.org/10.1128/AAC.00175-08.
- P. Bogaerts, C. Bauraing, A. Deplano and Y. Glupczynski, Antimicrob. Agents Chemother., 51, 1584 (2007); https://doi.org/10.1128/AAC.01603-06.
- D. Mijin, B. Bozic-Nedeljkovic, B. Bozic, I. Kovrlija, J. Ladarevic and G. Uscumlic, Turk. J. Chem., 42, 896 (2018); https://doi.org/10.3906/kim-1711-97.
- K.J. Al-Adilee, K.A. Abedalrazaq and Z.M. Al-Hamdiny, Asian J. Chem., 25, 10475 (2013); https://doi.org/10.14233/ajchem.2013.15735.
References
W.A. Al Masoudi, H.T. Mohammad and A.A. Hama, Int. Res. J. Pharm., 6, 386 (2015); https://doi.org/10.7897/2230-8407.06680.
D.A. Kummer, D. Li, A. Dion and A.G. Myers, Chem. Sci., 2, 1710 (2011); https://doi.org/10.1039/c1sc00303h.
M.G. Charest, C.D. Lerner, J.D. Brubaker, D. Siegel and A.G. Myers, Science, 308, 395 (2005); https://doi.org/10.1126/science.1109755.
C. Sun, Q. Wang, J.D. Brubaker, P. Wright, C.D. Lerner, K. Noson, M. Charest, D.R. Siegel, Y.-M. Wang and A.G. Myers, J. Am. Chem. Soc., 130, 17913 (2008); https://doi.org/10.1021/ja806629e.
K.C. Nicolaou, C. Nilewski, C.R.H. Hale, H.A. Ioannidou, A. ElMarrouni and L.G. Koch, Angew. Chem. Int. Ed., 52, 8736 (2013); https://doi.org/10.1002/anie.201304691.
Y.F. Baba, H. Elmsellem, Y.K. Rodi, H. Steli, C. Ad, Y. Ouzidan, F.O. Chahdi, N.K. Sebbar, E.M. Essassi and B. Hammouti, Der Pharma Chemica, 8, 159 (2016).
K.M. Kulkarni, S.A. Jadhav, P.B. Patil, V.R. Dhole and S.S. Patil, Der Pharma Chemica, 8, 38 (2016).
S.-J. Chao, X.-P. Hui, S. Li, Z.-Z. Qiu, P.-F. Xu, Z.-Y. Zhang, Q. Wang and Z.-W. Guan, J. Chin. Chem. Soc., 52, 539 (2005); https://doi.org/10.1002/jccs.200500079.
Ö. Ates, A. Kocabalkanli, N. Cesur and G. Ötük, Farmaco, 53, 541 (1998); https://doi.org/10.1016/S0014-827X(98)00063-9.
C.A.G.N. Montalbetti and V. Falque, Tetrahedron, 61, 10827 (2005); https://doi.org/10.1016/j.tet.2005.08.031.
N.M. Aljamali, Pak. J. Biotechnol., 15, 219 (2018).
S.N. Swamy, Basappa, B.S. Priya, B. Prabhuswamy, B.H. Doreswamy, J.S. Prasad and K.S. Rangappa, Eur. J. Med. Chem., 41, 531 (2006); https://doi.org/10.1016/j.ejmech.2005.12.009.
L. Jin, J. Chen, B. Song, Z. Chen, S. Yang, Q. Li, D. Hu and R. Xu, Bioorg. Med. Chem. Lett., 16, 5036 (2006); https://doi.org/10.1016/j.bmcl.2006.07.048.
M. Mohammed, N.M. Aljamali and N.A. Abbas, J. Global Pharm. Technol., 10, 20 (2018).
F.J. Uribe-Romo, J.R. Hunt, H. Furukawa, C. Klock, M. O’Keeffe and O.M. Yaghi, J. Am. Chem. Soc., 131, 4570 (2009); https://doi.org/10.1021/ja8096256.
N.M. Aljamali and I.O. Alfatlawi, Res. J. Pharm. Technol., 8, 1225 (2015); https://doi.org/10.5958/0974-360X.2015.00224.3.
M. Mohammed, N.M. Aljamali, S.A. Abdalrahman and W.A. Shubber, Biochem. Cell. Arch., 18, 847 (2018).
J.C. Hindson, B. Ulgut, R.H. Friend, N.C. Greenham, B. Norder, A. Kotlewski and T.J. Dingemans, J. Mater. Chem., 20, 937 (2010); https://doi.org/10.1039/B919159C.
R.J. Cremlyn, An Introduction to Organosulfur Chemistry, John Wiley & Sons: Chichester (1996).
N.M. Aljamali, S.M. Jawd, Z.M. Jawad and I.O. Alfatlawi, Res. J. Pharm. Technol., 10, 1683 (2017); https://doi.org/10.5958/0974-360X.2017.00297.9.
J. Drabowicz, J. Lewkowski, W. Kudelska and T. Girek, ed.: N. Kamble, S,S-Dialkylsulfoximides, In: Science of Synthesis, Thieme, vol. 39, pp. 154-173 (2008).
J. Drabowicz, J. Lewkowski, W. Kudelska and T. Girek, ed.: N. Kamble, S,S-Dialkylsulfonediimines, In: Science of Synthesis, Thieme, vol. 39, pp. 173–180 (2008).
Y. Zhang and N. Hogg, Free Radic. Biol. Med., 38, 831 (2005); https://doi.org/10.1016/j.freeradbiomed.2004.12.016.
S. Braverman, M. Cherkinsky and S. Levinger, ed.: N. Kamble, Alkylsulfur Trihalides, In: Science of Synthesis, Thieme, vol. 39, pp. 187-188 (2008).
J. Drabowicz, J. Lewkowski, W. Kudelska and T. Girek, ed.: N. Kamble, Dialkylsulfur Tetrahalides, In: Science of Synthesis, Thieme, vol. 39, pp. 123-124 (2008).
P. Arora, V. Arora, H.S. Lamba and D. Wadhwa, Int. J. Pharm. Res. Sci., 3, 2947 (2012).
N.M. Aljamali and D. Rahi, J. Chem. Pharm. Sci., 10, 1461 (2017).
H.S. Eman and N.M. Aljamali, J. Global Pharma Technol., 11, 165 (2017).
N.M. Aljamali, Reactions and Mechanisms, IJMRA Publication: Germany, edn 1 (2018).
I. Schneider, E. Keuleyan, R. Rasshofer, R. Markovska, A.M. Queenan and A. Bauernfeind, Antimicrob. Agents Chemother., 52, 2977 (2008); https://doi.org/10.1128/AAC.00175-08.
P. Bogaerts, C. Bauraing, A. Deplano and Y. Glupczynski, Antimicrob. Agents Chemother., 51, 1584 (2007); https://doi.org/10.1128/AAC.01603-06.
D. Mijin, B. Bozic-Nedeljkovic, B. Bozic, I. Kovrlija, J. Ladarevic and G. Uscumlic, Turk. J. Chem., 42, 896 (2018); https://doi.org/10.3906/kim-1711-97.
K.J. Al-Adilee, K.A. Abedalrazaq and Z.M. Al-Hamdiny, Asian J. Chem., 25, 10475 (2013); https://doi.org/10.14233/ajchem.2013.15735.