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Synthesis, Antioxidant and Antimicrobial Activity of 4-Aminophenol and 2-Aminobenzoic Acid Based Novel Azo Compounds
Corresponding Author(s) : Shahzad Murtaza
Asian Journal of Chemistry,
Vol. 27 No. 10 (2015): Vol 27 Issue 10
Abstract
In present work, 4-aminophenol and 2-aminobenzoic acid were diazotized at low temperature and novel azo compounds from 2-aminobenzoic acid, benzamide, 4-aminophenazone, 2-bromonitrobenzene and 4-dichlorobenzene were synthesized. The resulting compounds were characterized by m.p., UV-visible and FTIR spectroscopic technique. The synthesized compounds were screened for their antibacterial activity by using disc diffusion method. The bacterial strains Escherichia coli, Shigella sonnei, Streptococcus pyrogenes, Staphylococcus aureus and Neisseria gonorrhoea were used. The antioxidant activity was also performed by using DPPH method. Results revealed that azo compounds of 4-aminophenol with 2-aminobenzoic acid and 4-aminophenazone showed much better antibacterial activity against all strains while same azo compounds had good antioxidant activity.
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- O.O. Ajani, O.E. Akinremi, A.O. Ajani, A. Edobor-Osoh and W.U. Anake, Phys. Rev. Res. Int., 3, 28 (2013).
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References
O.O. Ajani, O.E. Akinremi, A.O. Ajani, A. Edobor-Osoh and W.U. Anake, Phys. Rev. Res. Int., 3, 28 (2013).
E. Aktan, B. Babur, Z. Seferoglu, T. Hokelek and E. Sahin, J. Mol. Struct., 1002, 113 (2011); doi:10.1016/j.molstruc.2011.07.007.
J. He, S. Bian, L. Li, J. Kumar, S. Tripathy and L. Samuelson, J. Phys. Chem. B, 104, 10513 (2000); doi:10.1021/jp001715r.
N. Ertan, Dyes Pigments, 44, 41 (1999); doi:10.1016/S0143-7208(99)00066-2.
F. Karci and N. Ertan, Dyes Pigments, 55, 99 (2002); doi:10.1016/S0143-7208(02)00102-X.
I. Sener, F. Karci, N. Ertan and E. Kilic, Dyes Pigments, 70, 143 (2006); doi:10.1016/j.dyepig.2005.05.003.
K.M. Rathod and N.S. Thakre, Chem. Sci. Trans., 2, 25 (2012); doi:10.7598/cst2013.254.
A.A. Jarrahpour, M. Motamedifar, K. Pakshir, N. Hadi and M. Zarei, Molecules, 9, 815 (2004); doi:10.3390/91000815.
A.Z. Sayed, M.S. Aboul-Fetouh and H.S. Nassar, J. Mol. Struct., 1010, 146 (2012); doi:10.1016/j.molstruc.2011.11.046.
M.N. Mohammed, J. Chem. Chem. EN, 6, 885 (2012).
Swati, Ginni, R. Karnawat, I.K. Sharma and P.S. Verma, Int. J. Appl. Biol. Pharm. Technol., 2, 332 (2012).
A.H. Shridhar, J. Keshavayya, H.J. Hoskeri and R.A.S. Ali, Int. Res. J. Pure Appl. Chem., 1, 119 (2011); doi:10.9734/IRJPAC/2011/493.
I.H.R. Tomi, A.H.R. Al-Daraji, R.R.T. Al-Qaysi, M.M. Hasson and K.H.D. Al-Dulaimy, 7, 687 (2014); doi:10.1016/j.arabjc.2010.12.003.
C.T. KeerthiKumar, J. Keshavayya, T. Rajesh and S.K. Peethambar, Int. J. Pharm. Pharm. Sci., 5(Suppl. 1), 296 (2013).
R.G. Child, R.G. Wilkinson and A. Tomcu-Fucik, Chem. Abstr., 87, 6031 (1997).
H.G. Garg and C. Prakash, J. Med. Chem., 15, 435 (1972); doi:10.1021/jm00274a035.
C.H. Browing, J.B. Cohen, S. Ellingworth and R. Gulbransen, Br. Med. J., 2(3269), 326 (1923); doi:10.1136/bmj.2.3269.326.
A. Khalid, M. Arshad and D.E. Crowley, Appl. Microbiol. Biotechnol., 78, 361 (2008); doi:10.1007/s00253-007-1302-4.
U. Pagga and D. Brown, Chemosphere, 15, 479 (1986); doi:10.1016/0045-6535(86)90542-4.
I.M.A. Awad, A.A.M. Aly, A.M. Abdel-Alim, R.A. Abdel-Aal and S.H. Ahmed, J. Inorg. Biochem., 33, 77 (1988); doi:10.1016/0162-0134(88)80036-9.
A.G. Makhsumov, M.A. Ergashev and F.A. Normatov, Pharm. Chem. J., 25, 798 (1991); doi:10.1007/BF00767262.
S.A. Ibrahim, M.A. El-Gahami, Z.A. Khafagi and S.A. El-Gyar, J. Inorg. Biochem., 43, 1 (1991); doi:10.1016/0162-0134(91)84063-F.
S. Samadhiya and H. Halve, Oriental J. Chem., 17, 119 (2001).
T.A. Farghaly and Z.A. Abdallah, ARKIVOC, 295 (2008).
H. Xu and X. Zeng, Bioorg. Med. Chem. Lett., 20, 4193 (2010); doi:10.1016/j.bmcl.2010.05.048.
L. Barros, R.C. Calhelha, J.A. Vaz, I.C.F.R. Ferreira, P. Baptista and L.M. Estevinho, Eur. Food Res. Technol., 225, 151 (2007); doi:10.1007/s00217-006-0394-x.
K. Uthayarasa, K. Pathmanathan, J.P. Jeyadevan and E.C. Jeyaseelan, Int. J. Integ. Biol., 10, 76 (2010).
M. Nagai, M. Tani, Y. Kishimoto, M. Iizuka, E. Saita, M. Toyozaki, T. Kamiya, M. Ikeguchi and K. Kondo, J. Clin. Biochem., 48, 203 (2011); doi:10.3164/jcbn.10-84.
S. Shamim, S. Murtaza and M.F. Nazar, J. Chem. Soc. Pak., (Submitted).
H. Karabiyik, N.O. Iskeleli, C. Albayrak and E. Agar, Struct. Chem., 18, 87 (2007); doi:10.1007/s11224-006-9130-1.
D.N. Nicolaides, D.R. Gautam, K.E. Litinas, D.J. Hadjipavlou-Litina and K.C. Fylaktakidou, Eur. J. Med. Chem., 39, 323 (2004); doi:10.1016/j.ejmech.2004.01.003.
R.S. Upadhayaya, J.K. Vandavasi, R.A. Kardile, S.V. Lahore, S.S. Dixit, H.S. Deokar, P.D. Shinde, M.P. Sarmah and J. Chattopadhyaya, Eur. J. Med. Chem., 45, 1854 (2010); doi:10.1016/j.ejmech.2010.01.024.
T. Chandra, N. Garg, S. Lata, K.K. Saxena and A. Kumar, Eur. J. Med. Chem., 45, 1772 (2010); doi:10.1016/j.ejmech.2010.01.009.
R. Kalla and J. Zablocki, Annu. Rep. Med. Chem., 44, 265 (2009); doi:10.1016/S0065-7743(09)04413-3.
M.W. Sabaa, N.A. Mohamed, R.R. Mohamed, N.M. Khalil and S.M. Abd El Latif, Carbohydr. Polym., 79, 998 (2010); doi:10.1016/j.carbpol.2009.10.024.
S.A.F. Rostom, Bioorg. Med. Chem., 18, 2767 (2010); doi:10.1016/j.bmc.2010.02.006.
S.A.F. Rostom, H.M.A. Ashour, H.A.A. El Razik, A. El Fattah H.A. El Fattah and N.N. El-Din, Bioorg. Med. Chem., 17, 2410 (2009); doi:10.1016/j.bmc.2009.02.004.