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Potent Antimicrobial Agents of 8-Aza-bicyclo[3.2.1]octyl hydrazide Derivatives: Synthesis and Biological Evaluation
Corresponding Author(s) : T. Lakshmi Viveka
Asian Journal of Chemistry,
Vol. 30 No. 9 (2018): Vol 30 Issue 9
Abstract
A facile synthesis of 8-aza-bicyclo[3.2.1]octyl hydrazide derivatives 4(a-m) can be achieved by modified Mannich reaction. Novelty of this research involves one pot synthesis of new modified Mannich based triazole derivatives using aromatic aldehydes and active hydrogen containing amides in the presence of ammonia and primary amine. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectroscopy. Among all the compounds which are screened for antibacterial and antifungal activities, hydrogen containing thiosemicarbazide moiety and 4,4-diflorocyclohexane carboxylic hydrazide has shown better activity against four bacterial strains and two fungal strains.
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References
S. Bala, N. Sharma, A. Kajal, S. Kamboj and V. Saini, Int. J. Med. Chem., Article ID 191072 (2014); https://doi.org/10.1155/2014/191072.
H.C. Yao and P. Resnick, J. Org. Chem., 30, 2832 (1965); https://doi.org/10.1021/jo01019a504.
R. Fusco and F. Sannicolo, J. Org. Chem., 46, 90 (1981); https://doi.org/10.1021/jo00314a019.
T. Iida and F.C. Chang, J. Org. Chem., 46, 2786 (1981); https://doi.org/10.1021/jo00326a037.
R.L. Frank and R.R. Phillips, J. Am. Chem. Soc., 71, 2804 (1949); https://doi.org/10.1021/ja01176a060.
Y. Koltin, Annu. Rep. Med. Chem., 25, 141 (1990).
A.J. Abdul Nasser, A. Idhayadhulla, R.S. Kumar and J. Selvin, J. Indian Heterocycl. Chem., 18, 399 (2009).
A. Idhayadhulla, R.S. Kumar, A.J. Abdul Nasser, J. Selvin and A. Manilal, Arab. J. Chem., 7, 994 (2014); https://doi.org/10.1016/j.arabjc.2010.12.025.
S. Fandakli, H.B. Serapbasoglu, A.D. Meltemyolal and A.K.G. Sengul, Turk. J. Chem., 36, 567 (2012); https://doi.org/10.3906/kim-1103-23.
S.G. Subramaniapillai, J. Chem. Sci., 125, 467 (2013); https://doi.org/10.1007/s12039-013-0405-y.
T. Plech, M. Wujec, M. Majewska, U. Kosikowska and A. Malm, Med. Chem. Res., 22, 2531 (2013); https://doi.org/10.1007/s00044-012-0248-y
H. Bayrak, A. Demirbas, S.A. Karaoglu and N. Demirbas, Eur. J. Med. Chem., 44, 1057 (2009); https://doi.org/10.1016/j.ejmech.2008.06.019.
L. Popiolek, A. Biernasiuk, K. Paruch, P. Patrejko and M. Wujec, Phosphorus, Sulfur, Silicon Rel. Elem., 192, 880 (2017); https://doi.org/10.1080/10426507.2017.1290629.
M. Sivakami, B. Natarajan and M. Vijayachandrasekar, Chem. Sci. Transac., 3, 1110 (2014); https://doi.org/10.7598/cst2014.837.
M.M. Alam, S. Nazreen, S. Haider, S. Shafi, M.S. Yar, H. Hamid and M.S. Alam, Arch. Pharm., 345, 203 (2012); https://doi.org/10.1002/ardp.201100128.
J. Chen, X.Y. Sun, K.Y. Chai, J.S. Lee, M.S. Song and Z.S. Quan, Bioorg. Med. Chem., 15, 6775 (2007); https://doi.org/10.1016/j.bmc.2007.08.004.
V. Vrdoljak, I. Dilovic, M. Rubcic, S. Kraljevic Pavelic, M. Kralj, D. Matkovic-Calogovic, I. Piantanida, P. Novak, A. Rozman and M. Cindric, Eur. J. Med. Chem., 45, 38 (2010); https://doi.org/10.1016/j.ejmech.2009.09.021.
M. Köksal, N. Gökhan, E. Küpeli, E. Yesilada and H. Erdogan, Arch. Pharm. Res., 30, 419 (2007); https://doi.org/10.1007/BF02980214.
D. Sharma, D. Chetia and M. Rudrapal, Asian J. Chem., 28, 782 (2016); https://doi.org/10.14233/ajchem.2016.19478.
R. Seth, S. Arora, S. Jain and N. Jain, J. Pharm. Technol. Res. Manage., 3, 57 (2015); https://doi.org/10.15415/jptrm.2015.31005.
S.J. Haycock-Lewandowski, A. Wilder and J. Åhman, J. Org. Process. Res. Dev., 12, 1094 (2008); https://doi.org/10.1021/op8000614.
T.L. Viveka, M. Saba, S.N.T. Sunitha, Y. Aparna and L.N. Sharada, World J. Pharm. Pharm. Sci., 4, 1087 (2016).