Synthesis of Novel 4(3H)-Quinazolinones with 1,2,3-Triazoles Moiety Conjugated by Schiff Base

Changhui Su; Xia Liu

doi:10.14233/ajchem.2014.17499

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Issue Published : July 28, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis of Novel 4(3H)-Quinazolinones with 1,2,3-Triazoles Moiety Conjugated by Schiff Base

https://doi.org/10.14233/ajchem.2014.17499

Changhui Su

Chemistry and Life Science College, Nanjing University Jinling College, Nanjing 210089, P.R. China

Xia Liu

Department of Science and Technology, Jiangsu Open University, Nanjing 210036, P.R. China

Corresponding Author(s) : Changhui Su

suchanghui1982@163.com

Asian Journal of Chemistry, Vol. 26 No. 16 (2014): Vol 26 Issue 16
Article Published : August 4, 2014

Abstract

We describe the synthesis of a novel quinazolin-4(3H)-ones i.e., (E)-3-[4-{4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl}benzylideneamino]-7-fluoro-2-methylquinazolin-4(3H)-one (7). Treatment of 4-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)benzaldehyde, which is synthesized via a click reaction of 4-azidobenzaldehyde and alkyne, with 3-amino-7-fluoro-2-methylquinazolin-4(3H)-one afforded the corresponding product in toluene catalyzed by TiCl₄. in vitro Cytotoxic activity of compound 7 against human hepatoma hepg2 cells is evaluated.

Keywords

Quinazolin-4(3H)-ones Cytotoxic activity Schiff base 1,2,3-Triazoles

Su, C., & Liu, X. (2014). Synthesis of Novel 4(3H)-Quinazolinones with 1,2,3-Triazoles Moiety Conjugated by Schiff Base. Asian Journal of Chemistry, 26(16), 5301–5304. https://doi.org/10.14233/ajchem.2014.17499

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References

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References

A.R. Katritzky, Y. Zhang and S.K. Singh, Heterocycles, 60, 1225 (2003); doi:10.3987/REV-02-562.

M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.E. Emmert, S.A. Garmon, D.R. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert and B.H. Yagi, J. Med. Chem., 43, 953 (2000); doi:10.1021/jm990373e.

H. Wamhoff, in eds.: A.R. Katritzky and C.W. Rees, In Comprehensive Heterocyclic Chemistry, Pergamon, Oxford, pp. 669 (1984).

Buckle, C.J.M. Rockell, H. Smith and B.A. Spicer, J. Med. Chem., 29, 2262 (1986); doi:10.1021/jm00161a022.

R. Alvarez, S. Velazquez, A. San-Felix, S. Aquaro, E.D. Clercq, C.-F. Perno, A. Karlsson, J. Balzarini and M.J. Camarasa, J. Med. Chem., 37, 4185 (1994); doi:10.1021/jm00050a015.

L.L. Brockunier, E.R. Parmee, H.O. Ok, M.R. Candelore, M.A. Cascieri, L.F. Colwell Jr., L. Deng, W.P. Feeney, M.J. Forrest, G.J. Hom, D.E. MacIntyre, L. Tota, M.J. Wyvratt, M.H. Fisher and A.E. Weber, Bioorg. Med. Chem. Lett., 10, 2111 (2000); doi:10.1016/S0960-894X(00)00422-4.

S.M. Roopan, F.N. Khan, J.S. Jin and R. Senthil Kumar, Res. Chem. Intermed., 37, 919 (2011); doi:10.1007/s11164-011-0301-3.

S.S. Parmar and R. Kumar, J. Med. Chem., 11, 635 (1968); doi:10.1021/jm00309a064.

K.-I. Ozaki, Y. Yamada, T. Oine, T. Ishizuka and Y. Iwasawa, J. Med. Chem., 28, 568 (1985); doi:10.1021/jm50001a006.

A. Kamal, E.V. Bharathi, M.J. Ramaiah, D. Dastagiri, J.S. Reddy, A. Viswanath, F. Sultana, S.N.C.V.L. Pushpavalli, M. Pal-Bhadra, H.K. Srivastava, G.N. Sastry, A. Juvekar, S. Sen and S. Zingde, Bioorg. Med. Chem., 18, 526 (2010); doi:10.1016/j.bmc.2009.12.015.

M.S. Mohamed, M.M. Kamel, E.M.M. Kassem, N. Abotaleb, S.I. Abd El-moez and M.F. Ahmed, Eur. J. Med. Chem., 45, 3311 (2010); doi:10.1016/j.ejmech.2010.04.014.

B.M. Srivastava, V.K. Bhalla, T.N. Shankar and K. Shanker, Arzneim. Forsch., 43, 595 (1993).

A. Hitkari, M. Saxena and A.K. Verma, Bull. Chim. Farm., 134, 609 (1995).

V. Alagarsamy and S. Murugesan, Chem. Pharm. Bull. (Tokyo), 55, 76 (2007); doi:10.1248/cpb.55.76.

A.C. Tinker, H.G. Beaton, N. Boughton-Smith, S.L. Cooper, L. Fraser-Rae, K. Hallam, P. Hamley, T. McInally, D.J. Nicholls, A.D. Pimm and A.V. Wallace, J. Med. Chem., 46, 913 (2003); doi:10.1021/jm0255926.

R.S. Hunoor, B.R. Patil, D.S. Badiger, R.S. Vadavi, K.B. Gudasi, V.M. Chandrashekhar and I.S. Muchchandi, Appl. Organomet. Chem., 25, 476 (2011); doi:10.1002/aoc.1790.

V. Alagarsamy, K. Dhanabal, P. Parthiban, G. Anjana, G. Deepa, B. Murugesan, S. Rajkumar and A.J. Beevi, J. Pharm. Pharmacol., 59, 669 (2007); doi:10.1211/jpp.59.5.0007.

T. Nagase, T. Mizutani, S. Ishikawa, E. Sekino, T. Sasaki, T. Fujimura, S. Ito, Y. Mitobe, Y. Miyamoto, R. Yoshimoto, T. Tanaka, A. Ishihara, N. Takenaga, S. Tokita, T. Fukami and N. Sato, J. Med. Chem., 51, 4780 (2008); doi:10.1021/jm8003834.

V. Alagarsamy, G. Murugananthan and R. Venkateshperumal, Biol. Pharm. Bull., 26, 1711 (2003); doi:10.1248/bpb.26.1711.

B.J. Stokes, C.V. Vogel, L.K. Urnezis, M. Pan and T.G. Driver, Org. Lett., 12, 2884 (2010); doi:10.1021/ol101040p.

Issue

Vol. 26 No. 16 (2014): Vol 26 Issue 16

Synthesis of Novel 4(3H)-Quinazolinones with 1,2,3-Triazoles Moiety Conjugated by Schiff Base

Corresponding Author(s) : Changhui Su

Abstract

Keywords

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