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Copyright (c) 2014 Aisha S.M. Hossan1, Abd El-Galil E. Amr2
This work is licensed under a Creative Commons Attribution 4.0 International License.
Antimicrobial and Pharmacological Activities of Some 3-Substituted Thieno[3,2-d]-pyrimidin-4(3H)-one
Corresponding Author(s) : Aisha S.M. Hossan1
Asian Journal of Chemistry,
Vol. 26 No. 24 (2014)
Abstract
A series of new 3-substituted-7-(2-chloro-6-ethoxypyridin-4-yl)-9-(2,4-dichlorophenyl)-2- methylpyrido[3',2':4,5]thieno[3,2-d]pyrimidin-4(3H)-one derivatives (3-10) were synthesized using 7-(2-chloro-6-ethoxypyridin-4-yl)-9-(aryl)-2-methyl-4H-pyrido-[3',2':4,5]thieno[3,2-d]-[1,3]oxazin-4-one (2a,b) as a starting material. All the newly synthesized compounds were evaluated for their antimicrobial activities. The antimicrobial screening showed that many of these obtained compounds have good antimicrobial activities comparable to streptomycin and fusidic acid as reference drugs. Also, the pharmacological screening showed that many compounds have good analgesic and antiparkinsonian activities comparable to Valdecoxib® and Benzotropine® as reference drugs. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, MS spectral data and elemental analysis.
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- N.A. Santagati, A. Caruso, V.M. Cutuli and F. Caccamo, IL Farmaco, 50, 689 (1995).
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- S.S. Laddha, S.G. Wadokar and S.K. Meghal, ARKIVOC, 1 (2006).
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- A.A. Fayed, A. El-Galil E. Amr, M.A. Al-Omar and E.E. Mostafa, Russ. J. Bioorg. Chem., 40, 308 (2014).
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- N.O. Al-Harbi, S.A. Bahashwan, A.A. Fayed, M.S. Aboonq and A.E. Amr, Int. J. Biol. Macromol., 57, 165 (2013).
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- A.E. Amr, A.M. Mohamed, S.F. Mohamed, N.A. Abdel-Hafez and A.G. Hammam, Bioorg. Med. Chem., 14, 5481 (2006).
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References
G. Steiner, W. Lubisch, A. Bach, F. Emling, K. Wicke, H.J. Teschendorf, B. Behl, F. Kerrigan and S. Cheetham, German Patent 19636769 (1996); Chem. Abstr., 128, 217381 (1998).
M. Modica, M. Santagati, A. Santagati, V. Cutuli, N. Mangano and A. Caruso, Pharmazie, 55, 500 (2000).
M.M. El-Kerdawy, M.Y. Yousif, A.A. El-Emam, M.A. Moustafa and M.A. El-Sherbeny, Boll. Chim. Farm., 135, 301 (1996).
K. Eichenberger, P. Schmidt and E. Schweizer, German Patent 1937459, (1969); Chem. Abstr., 72, 100743 (1970).
A. Kling, U.E.W. Lange, H. Mack, M.H.M. Bakker, K.U. Drescher, W. Hornberger, C.W. Hutchins, A. Möller, R. Müller, M. Schmidt, L. Unger, K. Wicke, K. Schellhaas and G. Steiner, Bioorg. Med. Chem. Lett., 15, 5567 (2005).
R.V. Chambhare, B.G. Khadse, A.S. Bobde and R.H. Bahekar, Eur. J. Med. Chem., 38, 89 (2003).
N.A. Santagati, A. Caruso, V.M. Cutuli and F. Caccamo, IL Farmaco, 50, 689 (1995).
L.D. Jennings, S.L. Kincaid, Y.D. Wang, G. Krishnamurthy, C.F. Beyer, J.P. McGinnis, M. Miranda, C.M. Discafani and S.K. Rabindran, Bioorg. Med. Chem. Lett., 15, 4731 (2005).
M.D. Meyer, R.J. Altenbach, F.Z. Basha, W.A. Carroll, S. Condon, S.W. Elmore, J.F. Kerwin, K.B. Sippy, K. Tietje, M.D. Wendt, A.A. Hancock, M.E. Brune, S.A. Buckner and I. Drizin, J. Med. Chem., 43, 1586 (2000).
S.S. Laddha, S.G. Wadokar and S.K. Meghal, ARKIVOC, 1 (2006).
P.N. Bhargava and M.R. Chaurasia, J. Med. Chem., 11, 404 (1968).
S.S. Parmar and R. Kumar, J. Med. Chem., 11, 635 (1968).
V. Alagarsamy, U.S. Pathak, R. Venkateshperumul, et al., Indian. J. Pharm. Sci., 65, 293 (2003).
E.B. Skibo, X. Huang, R. Martinez, R.H. Lemus, W.A. Craigo and R.T. Dorr, J. Med. Chem., 45, 5543 (2002).
A. Pandey, D.L. Volkots, J.M. Seroogy, J.W. Rose, J.-C. Yu, J.L. Lambing, A. Hutchaleelaha, S.J. Hollenbach, K. Abe, N.A. Giese and R.M. Scarborough, J. Med. Chem., 45, 3772 (2002).
A.S. Oganisyan, A.S. Noravyan, I.A. Dzhagatspanyan and A.G. Akopyan, Pharm. Chem. J., 35, 127 (2001).
B.V. Ashalatha, B. Narayana, K.K. Vijaya Raj and N. Suchetha Kumari, Eur. J. Med. Chem., 42, 719 (2007).
S. Selleri, F. Bruni, A. Costanzo, G. Guerrini, P. Malmberg Aiello, G. Iavarone and C. Martini, Eur. J. Med. Chem., 27, 985 (1992).
M. Kabak, A. Elmali and Y. Elerman, J. Mol. Struct., 477, 151 (1999).
P.R. Patel, B.T. Thaker and S. Zele, Indian J. Chem., 38A, 563 (1999).
P. Pattanayak, R. Sharma and P.K. Sahoo, Med. Chem. Res., 18, 351 (2009).
S.K. Gupta, P.K. Sharma, M. Bansal and B. Kumar, E-J. Chem., 8, 594 (2011).
A.S.M. Hossan, H.M.A. Abu-Melha, M.A. Al-Omar and A.E. Amr, Molecules, 17, 13642 (2012).
A.A. Fayed, A. El-Galil E. Amr, M.A. Al-Omar and E.E. Mostafa, Russ. J. Bioorg. Chem., 40, 308 (2014).
A.M. Al-Mohizea, M.A. Al-Omar, M.M. Abdalla and A.E. Amr, Int. J. Biol. Macromol., 50, 171 (2012).
N.O. Al-Harbi, S.A. Bahashwan, A.A. Fayed, M.S. Aboonq and A.E. Amr, Int. J. Biol. Macromol., 57, 165 (2013).
S.A. Bahashwan, N.O. Al-Harbi, A.A. Fayed, A.E. Amr, K.A. Shadid, A.M. Alalawi and I.M.S. Bassati, Int. J. Biol. Macromol., 51, 7 (2012).
N.H. Ouf and A.E. Amr, Monatsh. Chem., 139, 579 (2008).
A.E. Amr, A.M. Mohamed, S.F. Mohamed, N.A. Abdel-Hafez and A.G. Hammam, Bioorg. Med. Chem., 14, 5481 (2006).
A.-G.E. Amr, M.I. Hegab, A.A. Ibrahiem and M.M. Abdulla, Monatsh. Chem., 134, 1395 (2003).
A.-G.E. Amr, J. World Chem., 4, 201 (2009).
S.F. Mohamed, E.M. Flefel, A.E. Amr and D.N. Abd El-Shafy, Eur. J. Med. Chem., 45, 1494 (2010).
J.A. Smania Jr., F.D. Monache, E.F.A. Smania and R.S. Cuneo, Int. J. Med. Mushrooms, 1, 325 (1999).
K.F. Austen and W.E. Brocklehurst, J. Exp. Med., 113, 521 (1961).
A. Tgolsen, G.H. Rofland, O.G. Berge and K. Hole, J. Pharmacol. Ther., 25, 241 (1991).
M.D. Tyahr, The Basal Ganginia, Raven Press New York, p. 293 (1976).