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Copyright (c) 2014 Nagy M. Khalifa1, Ahmed M. Naglah1, Mohamed A. Al-Omar1, Abd El-Galil E. Amr1
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Screening of Some Novel Substituted Indoles Contained Fused Triazolo[1,5-a]pyridine and Thiazolo[3,2-a]pyridine Derivatives
Corresponding Author(s) : Nagy M. Khalifa1
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
A series of heterocyclic derivatives including 1H-pyrazol-4-carbonitrile (3), 1H pyrazol-5(4H)-one (4,5), 2-thioxopyrimidine-4,6-dione (6) 1,2,4-triazole-3(4H)-one (7), 1,6-diaminopyridine (9), triazolo[1,5-a]pyridin (10) and thiazolo[3,2-a]pyridine (11) moieties conjugated with 1-substituted indole moiety were synthesized on reaction with cyanoacetohydrazide, 3-amino-5-oxo-2-pyrazoline, thiobarbituric acid, thiosemicarbazide, malononitrile followed by cyanoacetohydrazide, different aromatic aldehydes and mercaptoacetic acid, respectively, by using 1-[2-(piperidin-1-yl)ethyl]-1H-indole-3-carbaldehyde (1) as starting material. The structures of all the newly synthesized products have been established on the basis of analytical and spectral data.The antimicrobial activity of some selected products was examined and some of them showed good activities.
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References
A. Majumder, R. Gupta and A. Jain, Green Chem. Lett. Rev., 6, 151 (2013).
S. Ke, X. Qian, F. Liu, N. Wang, Q. Yang and Z. Li, Eur. J. Med. Chem., 44, 2113 (2009).
L. Lu, J. Chen and W. Xiao, Acc. Chem. Res., 45, 1278 (2012).
M. Shiri, Chem. Rev., 112, 3508 (2012).
J. Song, T. Reeves, R. Fandrick, Z. Tan, K. Yee and H. Senanayake, ARKIVOC, 390 (2009).
D. Zhang, H. Song and Y. Qin, Acc. Chem. Res., 44, 447 (2011).
S. Ke, L. Shi, X. Cao, Q. Yang, Y. Liang and Z. Yang, Eur. J. Med. Chem., 54, 248 (2012).
K. Rao, S. Chhikara, N. Shirazi, R. Tiwari, K. Parang and A. Kumar, Bioorg. Med. Chem. Lett., 21, 3511 (2011).
C. Chiou, S. Chen, M. Chen, H. Li, L. Shi, X. Huang, W. Dai and J.-W. Chern, Chem. J. Chem. Med. Chem., 5, 1489 (2010).
K. Rao, S. Rao, N. Jain, J. Panwar and A. Kumar, Org. Med. Chem. Lett., 1, 10 (2011).
C. Granchi, S. Roy, A. De Simone, I. Salvetti, T. Tuccinardi, A. Martinelli, M. Macchia, M. Lanza, L. Betti, G. Giannaccini, A. Lucacchini, E. Giovannetti, R. Sciarrillo, G.J. Peters and F. Minutolo, Eur. J. Med. Chem., 46, 5398 (2011).
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E. Wincent, H. Shirani, J. Bergman, U. Rannug and T. Janosik, Bioorg. Med. Chem., 17, 1648 (2009).
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A. Bhattacharjee, M. Hartell, D. Nichols, R. Hicks, B. Stanton, J. van Hamont and W. Milhous, Eur. J. Med. Chem., 39, 59 (2004).
M. Prudhomme, Eur. J. Med. Chem., 38, 123 (2003).
L. He, H. Chang, T. Chou, N. Savaraj and C. Cheng, Eur. J. Med. Chem., 38, 101 (2003).
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P. Moreau, M. Sancelme, C. Bailly, S. Leonce, A. Pierre, J. Hickman, B. Pfeiffer and M. Prudhomme, Eur. J. Med. Chem., 36, 887 (2001).
X.Y. Zhu, L.G. Mardenborough, S. Li, A. Khan, W. Zhang, P. Fan, M. Jacob, S. Khan, L. Walker and S.Y. Ablordeppey, Bioorg. Med. Chem., 15, 686 (2007).
Y. Chen, H. Hung, C. Lu, K. Li and C. Tzeng, Bioorg. Med. Chem., 12, 6539 (2004).
J. Scovill, E. Blank, M. Konnick, E. Nenortas and T. Shapiro, Antimicrob. Agents Chemother., 46, 882 (2002).
V.M. Sharma, P. Prasanna, K.V. AdiSeshu, B. Renuka, C.V. Laxman Rao, G. Sunil Kumar, C.P. Narasimhulu, P. Aravind Babu, R.C. Puranik, D. Subramanyam, A.Venkateswarlu, S. Rajagopal, K.B.S. Kumar, C.S. Rao, N.V.S.R. Mamidi, D.S. Deevi, R. Ajaykumar and R. Rajagopalan, Bioorg. Med. Chem. Lett., 12, 2303 (2002).
C. Hong, G. Firestone and L. Bjeldanes, Biochem. Pharmacol., 63, 1085 (2002).
T. Garbe, M. Kobayashi, N. Shimizu, N. Takesue, M. Ozawa and H. Yukawa, J. Nat. Prod., 63, 596 (2000).
S. Bhati and A. Kumar, Eur. J. Med. Chem., 43, 2323 (2008).
D. Kaufmann, M. Pojarová, S. Vogel, R. Liebl, R. Gastpar, D. Gross, T. Nishino, T. Pfaller and E. von Angerer, Bioorg. Med. Chem., 15, 5122 (2007).
M. Pojarová, D. Kaufmann, R. Gastpar, T. Nishino, P. Reszka, P. Bednarski and E. von Angerer, Bioorg. Med. Chem., 15, 7368 (2007).
S. Vogel, D. Kaufmann, M. Pojarová, C. Müller, T. Pfaller, S. Kühne, P.J. Bednarski and E. Angerer, Bioorg. Med. Chem., 16, 6436 (2008).
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