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Abstract
Pyrazolo[3,4-d]pyrimidine derivatives were synthesized from 4-hydrazino-7-methoxy quinoline (2) with ethoxymethylenecyanoacetate afforded ethyl 5-amino-1-(7-methoxyquinolin-4-yl)-1H-pyrazole-4- carboxylate (3). The compound 3 was hydrolyzed to get 5-amino-1- (7-methoxyquinolin-4-yl)-1H-pyrazole-4-carboxylic acid (4) and then reacted with acetic anhydride to afford 1-(7-methoxyquinolin-4-yl)- 6-methylpyrazolo[3,4-d][1,3]oxazin-4(1H)-one (5), which was condensed with different aromatic amines to give a series of 5- substituted 1-(7-methoxyquinolin-4-yl)-6-methyl-5-aryl-1,5-dihydro- 4H-pyrazolo[3,4-d]pyrimidin-4-one (6). The newly synthesized compounds were characterized and evaluated for their antibacterial and antioxidant activity,and molecular docking studies.
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References
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References
J.C. Dharshan, K.A. Vishnumurthy, Y.D. Bodke, H.M. Vagdevi, N.D. Jayanna and R. Raghavendra, Der. Pharm. Chem., 4, 272 (2012).
S. Rostamizadeh, M. Nojavan, R. Aryan, H. Sadeghian and M. Davoodnejad, Chin. Chem. Lett., 24, 629 (2013); http://dx.doi.org/10.1016/j.cclet.2013.04.035.
L.P. Davies, S.C. Chow, J.H. Skerritt, D.J. Brown and G.A.R. Johnston, Life Sci., 34, 2117 (1984); http://dx.doi.org/10.1016/0024-3205(84)90310-2.
A.M. Elkhawaga, A.M. Kamal El-Dean, S.M. Radwan and M.M. Ahmed, Bull. Korean Chem. Soc., 30, 561 (2009); http://dx.doi.org/10.5012/bkcs.2009.30.3.561.
E. Dreassi, A.T. Zizzari, M. Mori, I. Filippi, A. Belore, A. Naldini, F. Carraro, A. Santucci, S. Schenone and M. Botta, Eur. J. Med. Chem., 45, 5958 (2010); http://dx.doi.org/10.1016/j.ejmech.2010.09.062.
M.M. El-Enany, M.M. Kamel, O.M. Khalil and H.B. El-Nassan, Eur. J. Med. Chem., 45, 5286 (2010); http://dx.doi.org/10.1016/j.ejmech.2010.08.048.
B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali and N.S. Shetty, Bioorg. Med. Chem., 14, 2040 (2006); http://dx.doi.org/10.1016/j.bmc.2005.10.053.
K.M. Dawood, A.M. Farag and N.A. Khedr, ARKIVOC, 166 (2008); http://dx.doi.org/10.3998/ark.5550190.0009.f16.
M.X. Jiang, N.C. Warshakoon and M.J. Miller, J. Org. Chem., 70, 2824 (2005); http://dx.doi.org/10.1021/jo0484070.
T.D. Penning, J.J. Talley, S.R. Bertenshaw, J.S. Carter, P.W. Collins, S. Docter, M.J. Graneto, L.F. Lee, J.W. Malecha, J.M. Miyashiro, R.S. Rogers, D.J. Rogier, S.S. Yu, G.D. Anderson, E.G. Burton, J.N. Cogburn, S.A. Gregory, C.M. Koboldt, W.E. Perkins, K. Seibert, A.W. Veenhuizen, Y.Y. Zhang and P.C. Isakson, J. Med. Chem., 40, 1347 (1997); http://dx.doi.org/10.1021/jm960803q.
S. Malladi, A.M. Isloor, S.K. Peethambar and H.K. Fun, Arabian J. Chem., 7, 1185 (2014); http://dx.doi.org/10.1016/j.arabjc.2013.12.020.
K.N. Mohana, B.N. Prasanna Kumar and L. Mallesha, Drug Invention Today, 5, 216 (2013); http://dx.doi.org/10.1016/j.dit.2013.08.004.
M. Kidwai and N. Negi, Monatsh. Chem., 128, 85 (1997); http://dx.doi.org/10.1007/BF00807642.
A.A. Joshi, S.S. Narkhede and C.L. Viswanathan, Bioorg. Med. Chem. Lett., 15, 73 (2005); http://dx.doi.org/10.1016/j.bmcl.2004.10.037.
M.A. Munawar, M. Azad, H.L. Siddiqui and F.-U.-H. Nasim, J. Chil. Chem. Soc., 55, 394 (2008); http://dx.doi.org/10.1002/jccs.200800058.
O.A. El-Sayed, B.A. Al-Bassam and M.E. Hussein, Arch. Pharm., 335, 403 (2002); http://dx.doi.org/10.1002/1521-4184(200212)335:9<403::AID-ARDP403>3.0.CO;2-9.
M.Y. Gavrilov, L.G. Mardanova, V.E. Kolla and M.E. Konshin, Pharm. Chem. J., 22, 554 (1988); http://dx.doi.org/10.1007/BF00763528.
O.A. El-Sayed, T.M. Al-Turki, H.M. Al-Daffiri, B.A. Al-Bassam and M.E. Hussein, Boll. Chim. Farm., 143, 227 (2004).
V.K. Ahluwalia, N. Kaila and S. Bala, Indian J. Chem., 26B, 700 (1987).
B. Andrews and M. Ahmed, Int. J. Pharm. Technol. Res., 6, 337 (2014).
N. Agarwal, S.K. Raghuwanshi, D.N. Upadhyay, P.K. Shukla and V.J. Ram, Bioorg. Med. Chem. Lett., 10, 703 (2000); http://dx.doi.org/10.1016/S0960-894X(00)00091-3.
M. Fares, S.M. Abou-Seri, H.A. Abdel-Aziz, S.E.-S. Abbas, M.M. Youssef and R.A. Eladwy, Eur. J. Med. Chem., 83, 155 (2014); http://dx.doi.org/10.1016/j.ejmech.2014.06.027.
A. Gangjee, Y. Zeng, J.J. McGuire and R.L. Kisliuk, J. Med. Chem., 43, 3125 (2000); http://dx.doi.org/10.1021/jm000130i.
C.J. Fabian and B.F. Kimler, Breast J., 7, 311 (2001); http://dx.doi.org/10.1046/j.1524-4741.2001.21570.x.
M. Parkkari, A.M. Paakkala, L. Salminen and K. Holli, Acta Ophthalmol. Scand., 81, 495 (2003); http://dx.doi.org/10.1034/j.1600-0420.2003.00116.x.
F. Cosman, Geriatr. Med., 19, 371 (2003); http://dx.doi.org/10.1016/S0749-0690(02)00114-3.
J.A. Mathew and N.N. Raj, Proceedings of the International Multi Conference of Engineers and Computer Scientists. Hong Kong Docking Studies on Anticancer Drugs for Breast Cancer Using Hex, IMECS; March 18-20, Hong Kong (2009).
S. Sobha and N. Raman, Int. J. Pharm. Bio. Sci., 3, 116 (2012).
N.D. Jayanna, H.M. Vagdevi, J.C. Dharshan, R. Raghavendra and S.B. Telkar, Med. Chem. Res., 22, 5814 (2013); http://dx.doi.org/10.1007/s00044-013-0565-9.
N.D. Jayanna, H.M. Vagdevi, J.C. Dharshan and T.R. Prashith Kekuda, J. Chem., Article ID 234074 (2013); http://dx.doi.org/10.1155/2013/234074.
N.D. Jayanna, H.M. Vagdevi, J.C. Dharshan, T.R. Prashith Kekuda, B.C. Hanumanthappa and B.C. Gowdarshivannanavar, J. Chem., Article ID 864385 (2012); http://dx.doi.org/10.1155/2013/234074.