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Synthesis of Novel Series of Quinolino[3,2-f][1,2,4]triazolo[3,4-b][1,3,4]-thiadiazepines Derivatives Incorporated with 3-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl] Moiety as Potent Antimicrobial Agent
Corresponding Author(s) : M. Idrees
Asian Journal of Chemistry,
Vol. 30 No. 9 (2018): Vol 30 Issue 9
Abstract
A novel series of quinolino[3,2-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine derivatives (7a-i) incorporated with 3-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl] moiety were synthesized through one-pot cyclo-condensation reaction of 5-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl]-4-amino-4H-1,2,4-triazole-3-thiol (4) with 2-chloroquinoline-3-carbaldehyde derivatives (6a-i) in presence of potassium carbonate in DMF. The characterization of newly synthesized compounds 3-[5-(benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl]-substituted quinolino[3,2-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepines (7a-i) was established by elemental analysis and spectral studies such as FT-IR, 1H NMR, 13C NMR and Mass spectra. All the synthesized compounds were screened in vitro for their antimicrobial activity against pathogenic microorganism including Gram-positive bacterial strains, S. aureus and Gram-negative bacteria strains E. coli, P. vulgaris and S. typhi at different concentration. The result of bioassay when compared with chloramphenicol as standard drug indicated good to moderate activity against these microbial strains.
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- B.D. Mert and K.M. Elattar, Curr. Org. Chem., 22, 386 (2018); https://doi.org/10.2174/1385272821666170920163512.
- T.S. Saleh, N.A. El-Rahman and R.S.A. Assaker, Green Chem. Lett. Rev., 5, 315 (2012); https://doi.org/10.1080/17518253.2011.628953.
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- B.S. Sasidhar and J.S. Biradar, Med. Chem. Res., 22, 3518 (2013); https://doi.org/10.1007/s00044-012-0370-x.
- G.C. Gonzalez-Munoz, M.P. Arce, C. Pérez, A. Romero, M. Villarroya, M.G. López, S. Conde and M.I. Rodríguez-Franco, Eur. J. Med. Chem., 81, 350 (2014); https://doi.org/10.1016/j.ejmech.2014.04.075.
- G.A. Showell, S. Bourrain and J.G. Neduvelil, J. Pharm. Chem. Biol. Sci., 4, 20 (2016).
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- A. Dandia, R. Singh and S. Khaturia, Bioorg. Med. Chem., 14, 1303 (2006); https://doi.org/10.1016/j.bmc.2005.09.057.
- M. Quaraishi, A. Dandia, S. Gupta and L. Sudheer, J. Mater. Environ. Sci., 3, 993 (2012).
- Y. Hangun-Balkir and M.L. McKenney, Green Chem. Lett. Rev., 5, 147 (2012); https://doi.org/10.1080/17518253.2011.603756.
- G. Marfe and C. Stefano, Recent Pat. Anti-Canc., 5, 58 (2010); https://doi.org/10.2174/157489210789702163.
- Z. Brzozowski, J. Slawiñski, F. S¹czewski, A. Innocenti and C.T. Supuran, Eur. J. Med. Chem., 45, 2396 (2010); https://doi.org/10.1016/j.ejmech.2010.02.020.
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- A.R. Farghalya, E. De Clercq and H. El-Kashefa, ARKIVOC, 137 (2006); https://doi.org/10.3998/ark.5550190.0007.a17.
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- B. Tozkoparan, G. Aktay and E. Yesilada, Farmaco, 57, 145 (2002); https://doi.org/10.1016/S0014-827X(01)01195-8.
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- M.K. Raina and P.K. Das, Indian J. Med. Res., 59, 614 (1971).
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- R. Silvestri, M. Artico and E. Pag Nozzi, Farmaco, 51, 425 (1996).
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- J. Duan, L.C. Hen, R.J. Chemey, C.P. Decicco and M.E. Voss, PCT Int. Appl. WO, 41246 (1999).
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- M. Kuroda, M. Amano and F. Noboru, Ger. Often. DF, 4, 184 (1991).
- N.J. Siddiqui, M. Idrees, N.T. Khati and M.G. Dhonde, Der Chem. Sinica, 6, 49 (2015)
References
B.D. Mert and K.M. Elattar, Curr. Org. Chem., 22, 386 (2018); https://doi.org/10.2174/1385272821666170920163512.
T.S. Saleh, N.A. El-Rahman and R.S.A. Assaker, Green Chem. Lett. Rev., 5, 315 (2012); https://doi.org/10.1080/17518253.2011.628953.
T.A. Kalinina, P.E. Prokhorova, T.V. Glukhareva and Yu.Yu. Morzherin, Izv. Akad. Nauk, Ser. Khim. Russ. Chem. Bull. Int. Ed., 60, 981 (2011); https://doi.org/10.1007/s11172-011-0154-3.
B.S. Sasidhar and J.S. Biradar, Med. Chem. Res., 22, 3518 (2013); https://doi.org/10.1007/s00044-012-0370-x.
G.C. Gonzalez-Munoz, M.P. Arce, C. Pérez, A. Romero, M. Villarroya, M.G. López, S. Conde and M.I. Rodríguez-Franco, Eur. J. Med. Chem., 81, 350 (2014); https://doi.org/10.1016/j.ejmech.2014.04.075.
G.A. Showell, S. Bourrain and J.G. Neduvelil, J. Pharm. Chem. Biol. Sci., 4, 20 (2016).
Z.A. Kaplancikli, M.D. Altintop, G.T. Zitouni, A. Ozdemir, R. Demirel, U.A. Mohsen and W. Hussein, Cukurova Med. J., 38, 103 (2013).
M. Gupta, S. Paul and R. Gupta, Indian J. Chem., 48B, 460 (2009).
A. Dandia, R. Singh and S. Khaturia, Bioorg. Med. Chem., 14, 1303 (2006); https://doi.org/10.1016/j.bmc.2005.09.057.
M. Quaraishi, A. Dandia, S. Gupta and L. Sudheer, J. Mater. Environ. Sci., 3, 993 (2012).
Y. Hangun-Balkir and M.L. McKenney, Green Chem. Lett. Rev., 5, 147 (2012); https://doi.org/10.1080/17518253.2011.603756.
G. Marfe and C. Stefano, Recent Pat. Anti-Canc., 5, 58 (2010); https://doi.org/10.2174/157489210789702163.
Z. Brzozowski, J. Slawiñski, F. S¹czewski, A. Innocenti and C.T. Supuran, Eur. J. Med. Chem., 45, 2396 (2010); https://doi.org/10.1016/j.ejmech.2010.02.020.
K.S. Bhat, B. Poojary, D.J. Prasad, P. Naik and B.S. Holla, Eur. J. Med. Chem., 44, 5066 (2009); https://doi.org/10.1016/j.ejmech.2009.09.010.
A.R. Farghalya, E. De Clercq and H. El-Kashefa, ARKIVOC, 137 (2006); https://doi.org/10.3998/ark.5550190.0007.a17.
R. Azuma, M. Saeki, Y. Yamamoto, Y. Hagiwara, L.B. Grochow and R. Donehower, Xenobiotica, 32, 63 (2002); https://doi.org/10.1080/00498250110085818.
J.F.F. Liegeois, J. Bruhwyler, J. Damas, T.P. Nguyen, E.M.G. Chleide, M.G.A. Mercier, F.A. Rogister and J.E. Delarge, J. Med. Chem., 36, 2107 (1993); https://doi.org/10.1021/jm00067a009.
M. Sekar and K.J. Rajendra Prasad, J. Chem. Technol. Biotechnol., 72, 50 (1998); https://doi.org/10.1002/(SICI)1097-4660(199805)72:1<50::AIDJCTB868>3.0.CO;2-E.
J.S. Biradar, P. Rajesab, N.J. Biradar and S.B. Somappa, Scient. World J., 581737 (2014); https://doi.org/10.1155/2014/581737.
B. Tozkoparan, G. Aktay and E. Yesilada, Farmaco, 57, 145 (2002); https://doi.org/10.1016/S0014-827X(01)01195-8.
D. Giannotti, G. Viti, P. Sbraci, V. Pestellini, G. Volterra, F. Borsini, A. Lecci, A. Meli, P. Dapporto and P. Paoli, J. Med. Chem., 34, 1356 (1991); https://doi.org/10.1021/jm00108a018.
M.K. Raina and P.K. Das, Indian J. Med. Res., 59, 614 (1971).
M. Kidwai, P. Sapra, P. Misra, R.K. Saxena and M. Singh, Bioorg. Med. Chem., 9, 217 (2001); https://doi.org/10.1016/S0968-0896(00)00245-5.
R. Silvestri, M. Artico and E. Pag Nozzi, Farmaco, 51, 425 (1996).
A. Monge, E. Alvarez, M. San, E. Nadal, I. Ruiz, M. Font, J. MartinezIrujo, E. Santiago, I. Prieto, J. Lasarte, P. Sarobe and F. Borras, Drug Des. Discov., 14, 291 (1997).
K. Walczak, A. Gondela and J. Suwinski, Eur. J. Med. Chem., 39, 849 (2004); https://doi.org/10.1016/j.ejmech.2004.06.014.
J. Duan, L.C. Hen, R.J. Chemey, C.P. Decicco and M.E. Voss, PCT Int. Appl. WO, 41246 (1999).
V.M. Reddy and K.R. Reddy, Chem. Pharm. Bull. (Tokyo), 58, 1081 (2010); https://doi.org/10.1248/cpb.58.1081.
J.K. Sahu, A. Kaushik and S. Ganguly, J. Adv. Pharm. Technol. Res., 5, 90 (2014); https://doi.org/10.4103/2231-4040.133434.
S.S. Rajput, Int. J. Pharm. Pharm. Sci., 4, 164 (2012).
A.S. Geetha, R. Vijayaraj and T.R. Kumar, Int. J. Res. Pharm. Biomed. Sci., 2, 155 (2011).
A.A. Shchipalkin, M.L. Petrov and V.A. Kuznetsov, Russ. J. Org. Chem., 47, 1209 (2011); https://doi.org/10.1134/S107042801108015X.
M. Kuroda, M. Amano and F. Noboru, Ger. Often. DF, 4, 184 (1991).
N.J. Siddiqui, M. Idrees, N.T. Khati and M.G. Dhonde, Der Chem. Sinica, 6, 49 (2015)