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Synthetic Approach for Novel Fluorine Substituted Thiadiazaphosphole Fused 1,2,4-Triazinopyridiazine Moieties as Bactericidal Agents
Corresponding Author(s) : Ola Ahmad Abu Ali
Asian Journal of Chemistry,
Vol. 28 No. 4 (2016): Vol 28 Issue 4
Abstract
Novel fluorine substituted thiadiazaphosphole fused 1,2,4-triazino pyridiazines (7 and 8) were synthesized by refluxing of 4-amino-6-styryl-3-mercapto-1,2,4-triazin-5-one (2) with triethylphosphite and/or triethylphospate in dry ethyl benzene followed by cycloaddition with hydrazine in warm ethanol-piperidine and finally boil with trifluoroacetic anhydride in dioxane. Structure of the products was elucidated with the help of elemental analysis and spectral data. All the target compounds evaluated as bactericidal agents against Escherichia coli compared with chloromycetin as standard antibiotic.
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- R.M. Abdel-Rahman, M.S.T. Makki and A.N. Al-Romaizan, Int. J. Org. Chem., 4, 247 (2014); doi:10.4236/ijoc.2014.44028.
- A.N. Al-Romaizan, M.S.T. Makki and R.M. Abdel-Rahman, Int. J. Org. Chem., 4, 154 (2014); doi:10.4236/ijoc.2014.42017.
- T.E. Ali, R.M. Abdel-Rahman, F.I. Hanafy and S.M. El-Edfawy, Phosphorus Sulfur Silicon Rel. Elem., 183, 2565 (2008); doi:10.1080/10426500801967864.
- R.M. Abdel-Rahman, Trends in Heterocycl. Chem., 8, 187 (2002).
- R.M. Abdel-Rahman, M.A. Ibrahim and T.E. Ali, Eur. J. Chem., 1, 383 (2010); doi:10.5155/eurjchem.1.4.388-396.154.
- Z. El-Gendy, J.M. Morsy, H.A. Allimony, W.R. Abdel-Monem and R.M. Abdel-Rahman, Pharmazie, 56, 376 (2001).
- Z. El-Gendy, J.M. Morsy, H.A. Allimony, W.R. Abdel-Monem and R.M. Abdel-Rahman, Phosphorus Sulfur Silicon Rel. Elem., 178, 2055 (2003); doi:10.1080/10426500390228738.
- A.S. Al-Harbi, R.M. Abdel-Rahman and A.M. Asiri, Eur. J. Chem., 6, 63 (2015); doi:10.5155/eurjchem.6.1.63-70.1147.
- A.S. Al-Harbi, R.M. Abdel-Rahman and A.M. Asiri, Int. J. Org. Chem., 4, 142 (2014).
- M.S.T. Makki, R.M. Abdel-Rahman and K.A. Khan, J. Chem., Article ID 430573 (2014). http://dx.doi.org110.115/2014/430573.
- T.E. Ali and R.M. Abdel-Rahman, J. Sulfur Chem., 35, 339 (2014); doi:10.1080/17415993.2014.896363.
- R.M. Abdel-Rahman and T.E. Ali, Monatsh. Chem., 144, 1243 (2013); doi:10.1007/s00706-013-0934-6.
- H.A. Zaher, R. Mohammady and Y.A. Ibrahim, J. Heterocycl. Chem., 21, 905 (1984); doi:10.1002/jhet.5570210355.
- T.E. Ali and S.S. Halacheva, Heteroatom Chem., 20, 117 (2009); doi:10.1002/hc.20520.
- T.E. Ali, Phosphorus Sulfur Silicon Rel. Elem., 185, 88 (2009); doi:10.1080/10426500802713309.
- C.D. Reddy, G.T. Reddy and M.S. Reddy, Asian J. Chem., 5, 291 (1993).
- I.B. Paek, S.Y. Kim, M.S. Kim, J. Kim, G. Lee and H.S. Lee, J. Toxicol. Environ. Health, 70, 1356 (2007); doi:10.1080/15287390701434307.
- J.Y. Winum, M. Rami, A. Scozzafava, J.L. Montero and C. Supuran, Med. Res. Rev., 28, 445 (2008); doi:10.1002/med.20112.
- R.M. Abdel-Rahman, M.S.T. Makki, T.E. Ali and M.A. Ibrahim, Curr. Org. Synth., 10, 136 (2013); doi:10.2174/1570179411310010006#sthash.bRXt3huG.dpuf.
- R.M. Abdel-Rahman, Pharmazie, 56, 18 (2001).
- C.H. Collins, Microbiological Methods, Butterworths, London, p. 364 (1967).
References
R.M. Abdel-Rahman, M.S.T. Makki and A.N. Al-Romaizan, Int. J. Org. Chem., 4, 247 (2014); doi:10.4236/ijoc.2014.44028.
A.N. Al-Romaizan, M.S.T. Makki and R.M. Abdel-Rahman, Int. J. Org. Chem., 4, 154 (2014); doi:10.4236/ijoc.2014.42017.
T.E. Ali, R.M. Abdel-Rahman, F.I. Hanafy and S.M. El-Edfawy, Phosphorus Sulfur Silicon Rel. Elem., 183, 2565 (2008); doi:10.1080/10426500801967864.
R.M. Abdel-Rahman, Trends in Heterocycl. Chem., 8, 187 (2002).
R.M. Abdel-Rahman, M.A. Ibrahim and T.E. Ali, Eur. J. Chem., 1, 383 (2010); doi:10.5155/eurjchem.1.4.388-396.154.
Z. El-Gendy, J.M. Morsy, H.A. Allimony, W.R. Abdel-Monem and R.M. Abdel-Rahman, Pharmazie, 56, 376 (2001).
Z. El-Gendy, J.M. Morsy, H.A. Allimony, W.R. Abdel-Monem and R.M. Abdel-Rahman, Phosphorus Sulfur Silicon Rel. Elem., 178, 2055 (2003); doi:10.1080/10426500390228738.
A.S. Al-Harbi, R.M. Abdel-Rahman and A.M. Asiri, Eur. J. Chem., 6, 63 (2015); doi:10.5155/eurjchem.6.1.63-70.1147.
A.S. Al-Harbi, R.M. Abdel-Rahman and A.M. Asiri, Int. J. Org. Chem., 4, 142 (2014).
M.S.T. Makki, R.M. Abdel-Rahman and K.A. Khan, J. Chem., Article ID 430573 (2014). http://dx.doi.org110.115/2014/430573.
T.E. Ali and R.M. Abdel-Rahman, J. Sulfur Chem., 35, 339 (2014); doi:10.1080/17415993.2014.896363.
R.M. Abdel-Rahman and T.E. Ali, Monatsh. Chem., 144, 1243 (2013); doi:10.1007/s00706-013-0934-6.
H.A. Zaher, R. Mohammady and Y.A. Ibrahim, J. Heterocycl. Chem., 21, 905 (1984); doi:10.1002/jhet.5570210355.
T.E. Ali and S.S. Halacheva, Heteroatom Chem., 20, 117 (2009); doi:10.1002/hc.20520.
T.E. Ali, Phosphorus Sulfur Silicon Rel. Elem., 185, 88 (2009); doi:10.1080/10426500802713309.
C.D. Reddy, G.T. Reddy and M.S. Reddy, Asian J. Chem., 5, 291 (1993).
I.B. Paek, S.Y. Kim, M.S. Kim, J. Kim, G. Lee and H.S. Lee, J. Toxicol. Environ. Health, 70, 1356 (2007); doi:10.1080/15287390701434307.
J.Y. Winum, M. Rami, A. Scozzafava, J.L. Montero and C. Supuran, Med. Res. Rev., 28, 445 (2008); doi:10.1002/med.20112.
R.M. Abdel-Rahman, M.S.T. Makki, T.E. Ali and M.A. Ibrahim, Curr. Org. Synth., 10, 136 (2013); doi:10.2174/1570179411310010006#sthash.bRXt3huG.dpuf.
R.M. Abdel-Rahman, Pharmazie, 56, 18 (2001).
C.H. Collins, Microbiological Methods, Butterworths, London, p. 364 (1967).