Synthesis of a Novel Class of Some 1,3,5-Triazine Derivatives and their  Anti-HIV Activity

Sweta D. Desai; Kishor R. Desai; Kishor H. Chikhalia; Christophe Pannecouque; Erik De Clercq

doi:10.37285/ijddd.2.1.2

Articles

Vol. 2 No. 1 (2011): January – March 2011

Synthesis of a Novel Class of Some 1,3,5-Triazine Derivatives and their Anti-HIV Activity

Sweta D. Desai^▸^▾
Kishor R. Desai^▸^▾
Kishor H. Chikhalia^▸^▾
Christophe Pannecouque^▸^▾
Erik De Clercq^▸^▾

Requires Subscription or Fee pdf (INR 2000)

DOI: https://doi.org/10.37285/ijddd.2.1.2
Submitted: November 28, 2024
Published: 2024-12-08

Abstract

Novel substituted s-triazine based derivatives were prepared by condensation of 2,4,6-trichloro-1,3,5-s-triazine with anisole, p-trifluoromethyl aniline and amino acid chloride, upon which the compounds were derivatized to their phenyl(thio)urea derivatives, and evaluated for their antiviral activity against human immunodefiency virus HIV-1 (IIIB) and HIV-2 (ROD). The structures of novel synthesized compounds have been established on the basis of 1H NMR, FTIR spectral data and elemental analysis.

References

[1] Turner, B. G.; Summers, M. F. J. Mol. Biol. 1999, 285, 1.
[2] Arnold, E.; Das, K.; Ding, J.; Yadav, P. N.; Hsiou, Y.; Boyer, P. L.; Hughes, S. H. Drug Des. Discov. 1996, 13, 29.
[3] Gazzard, B.; Moyle, M. Lancet. 1998, 352, 314.
[4] De Clercq, E. Trends Pharmacol. Sci. 1990, 11, 198.
[5] Aiterman, M.; Samulsson, B. J.; Danielson, H. J. Med. Chem. 1984, 1, 3782.
[6] Srinivas, K.; Srinivas, U.; Bhanuprasad, K.; Kishore, K. H.; Rao, J.; Murty, U. S. N. Bioorg. Med. Chem. Lett. 2005, 15, 1121.
[7] Desai, K. R.; Chikhalia, K. H.; Patel, R. B. J. Ind. Chem. Soc. 2003, 80, 138.
[8] Nishimura, N.; Kato, A.; Maeba, I. Carbohyd. Res. 2001, 331(1), 77.
[9] Mahajan, D. H.; De Clercq, E.; Chikhalia, K. H. Arch Pharmazie, 2009, 342, 281.
[10] Patel, R. B.; Chikhalia, K. H.; Pannecouque, C.; De Clercq, E. J. Braz. Chem. Soc. 2007, 18(2), 312.
[11] Dave, M. P.; Thaker, K. A.; Patel, J. M.; Langalia, N. A. J. Ind. Chem. Soc. 1984, 61, 237.
[12] Henke, B. R.; Consler, T. G.; Go, N.; Hale, R. L.; Hohman, D. R.; Jones, S. A.; Lu, A. T.; Moore, L. B.; Moore, J. T.; Orband-Miller, L. A.; Robinett, R. G.; Shearin, J.; Spearing, P. K.; Stewart, E. L.; Turnbull, P. S.; Weaver, S. L.; Williams, S. P.; Wisely, G. B.; Lambert, M. H. J. Med. Chem. 2002, 455, 492.
[13] Seffernick, J. L.; Tavish, M. H.; Wackett, L. P.; De Souza,M. L.; Osborne, J. P.; Sadowsky, M. J. Biochemistry. 2002, 41, 14430.
[14] Ludovici, D. W.; Kavash, R. W.; Kukla, M. J.; Ho, C. Y.; Ye, H.; De Corte, B. L.; Andries, K.; De Bethune, M. P.; Azijn, H.; Pauwels, R.; Moereels, H. E.; Heeres, J.; Koymans, L. M.; De Jonge, M. R.; Van Aken, K. J.; Daeyaert, F. F.; Lewi, P. J.; Das, K.; Arnold, E.; Janssen, P. A. Bioorg. Med. Chem. Lett. 2001, 11, 2229.
[15] Alessandro, B.; Stewart, M. L.; Gilbert, I. H.; Barrett, M. P.; Vanessa, Y.; Bueno, G. J.; Brun, R. J. Med. Chem. 2005, 48, 5570.
[16] Afonso, C. A. M.; Lourenco, N. M. T.; Rosatella, A. A. Molecules. 2006, 11(1), 81.
[17] Blotny, G. Tetrahedron, 2006, 62, 9507.
[18] Ricci, A.; Carra, A.; Torelli, A.; Maggiali, C. A.; Vicini, P.; Zani, F.; Branca, C. Plant Growth Reg. 2001, 34, 167.
[19] Chikhalia, K. H.; Vashi, D. B.; Patel, M. J. J. Enz. Inhi. & Med. Chem. 2009, 24, 617.
[20] Nag, S.; Pathak, R.; Kumar, M.; Shukla, P. K.; Batra, S. Bioorg. Med. Chem. Lett. 2006, 16, 3824.
[21] Taylor, A. E.; Terry, R. J.; Godfrey, D. G. Brit. J. Pharmacol. Chemother. 1956, 11, 71.
[22] Frey, R. R.; Curtin, M. L.; Albert, D. H.; Glaser, K. B.; Pease, L. J.; Soni, N. B.; Marcotte, P.; Bukofzer, G.; Li, J.; Davidsen, S. K.; Michaelides, M. R. J. Med. Chem. 2008, 51, 3777.
[23] Easmon, J.; Purstinger, G.; Heinisch, G.; Roth, T.; Fiebig,H. H.; Holzer, W.; Jager, W.; Jenny, M.; Hofmann, J. J. Med. Chem. 2001, 44, 2164.
[24] Campiani, G.; Fabbrini, M.; Morelli, E.; Nacci, V; Greco, G.; Novellino, E.; Bergamini, A.; Faggioli, E.; Uccella, I.; Bolacchi, F.; Marini, S.; Coletta, M.; Fracasso, C.; Caccia,S. Antiviral Chem. Chemother. 2000, 11, 141.
[25] Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. J. Virol. Methods. 1988, 20, 309.
[26] Bruckner, H.; Strecker, B. J. Chromatogr. 1992, 627, 97.

Keywords

s-triazine
urea
thiourea
anti-HIV activity

How to Cite

Desai, S. D., Desai, K. R., Chikhalia, K. H., Pannecouque, C., & Clercq, E. D. (2024). Synthesis of a Novel Class of Some 1,3,5-Triazine Derivatives and their Anti-HIV Activity . International Journal of Drug Design and Discovery, 2(1), 361–368. https://doi.org/10.37285/ijddd.2.1.2

Most read articles by the same author(s)

Esra Tatar, İlkay Küçükgüzel, Ş.Güniz Küçükgüze, Feyza Yılmaz-Demircan, Erik De Clercq, Graciela Andrei, Robert Snoeck, Christophe Pannecouque, Fikrettin Şahin, Ömer Faruk Bayrak, Synthesis, Anti-Tuberculosis and Antiviral Activity of Novel 2-isonicotinoylhydrazono-5-arylidene-4-thiazolidinones , International Journal of Drug Design and Discovery: Vol. 1 No. 1 (2010): January-March 2010
Rakesh R. Somani, Anuj G. Agrawal, Umesh V. Bhanushali, Pushkar P. Kalantri, Erik De Clercq, Synthesis and Biological Evaluation of some 2,5-Disubstituted -1,3,4- Oxadiazole Derivatives , International Journal of Drug Design and Discovery: Vol. 2 No. 1 (2011): January – March 2011
Rakesh R. Somani, Anuj G. Agrawal, Pushkar P. Kalantri, Pratibha S. Gavarkar, Erik De Clercq, Investigation of 1, 3, 4-Oxadiazole Scaffold as Potentially Active Compounds , International Journal of Drug Design and Discovery: Vol. 2 No. 1 (2011): January – March 2011

[1] [1] Turner, B. G.; Summers, M. F. J. Mol. Biol. 1999, 285, 1.

[2] [2] Arnold, E.; Das, K.; Ding, J.; Yadav, P. N.; Hsiou, Y.; Boyer, P. L.; Hughes, S. H. Drug Des. Discov. 1996, 13, 29.

[3] [3] Gazzard, B.; Moyle, M. Lancet. 1998, 352, 314.

[4] [4] De Clercq, E. Trends Pharmacol. Sci. 1990, 11, 198.

[5] [5] Aiterman, M.; Samulsson, B. J.; Danielson, H. J. Med. Chem. 1984, 1, 3782.

[6] [6] Srinivas, K.; Srinivas, U.; Bhanuprasad, K.; Kishore, K. H.; Rao, J.; Murty, U. S. N. Bioorg. Med. Chem. Lett. 2005, 15, 1121.

[7] [7] Desai, K. R.; Chikhalia, K. H.; Patel, R. B. J. Ind. Chem. Soc. 2003, 80, 138.

[8] [8] Nishimura, N.; Kato, A.; Maeba, I. Carbohyd. Res. 2001, 331(1), 77.

[9] [9] Mahajan, D. H.; De Clercq, E.; Chikhalia, K. H. Arch Pharmazie, 2009, 342, 281.

[10] [10] Patel, R. B.; Chikhalia, K. H.; Pannecouque, C.; De Clercq, E. J. Braz. Chem. Soc. 2007, 18(2), 312.

[11] [11] Dave, M. P.; Thaker, K. A.; Patel, J. M.; Langalia, N. A. J. Ind. Chem. Soc. 1984, 61, 237.

[12] [12] Henke, B. R.; Consler, T. G.; Go, N.; Hale, R. L.; Hohman, D. R.; Jones, S. A.; Lu, A. T.; Moore, L. B.; Moore, J. T.; Orband-Miller, L. A.; Robinett, R. G.; Shearin, J.; Spearing, P. K.; Stewart, E. L.; Turnbull, P. S.; Weaver, S. L.; Williams, S. P.; Wisely, G. B.; Lambert, M. H. J. Med. Chem. 2002, 455, 492.

[13] [13] Seffernick, J. L.; Tavish, M. H.; Wackett, L. P.; De Souza,M. L.; Osborne, J. P.; Sadowsky, M. J. Biochemistry. 2002, 41, 14430.

[14] [14] Ludovici, D. W.; Kavash, R. W.; Kukla, M. J.; Ho, C. Y.; Ye, H.; De Corte, B. L.; Andries, K.; De Bethune, M. P.; Azijn, H.; Pauwels, R.; Moereels, H. E.; Heeres, J.; Koymans, L. M.; De Jonge, M. R.; Van Aken, K. J.; Daeyaert, F. F.; Lewi, P. J.; Das, K.; Arnold, E.; Janssen, P. A. Bioorg. Med. Chem. Lett. 2001, 11, 2229.

[15] [15] Alessandro, B.; Stewart, M. L.; Gilbert, I. H.; Barrett, M. P.; Vanessa, Y.; Bueno, G. J.; Brun, R. J. Med. Chem. 2005, 48, 5570.

[16] [16] Afonso, C. A. M.; Lourenco, N. M. T.; Rosatella, A. A. Molecules. 2006, 11(1), 81.

[17] [17] Blotny, G. Tetrahedron, 2006, 62, 9507.

[18] [18] Ricci, A.; Carra, A.; Torelli, A.; Maggiali, C. A.; Vicini, P.; Zani, F.; Branca, C. Plant Growth Reg. 2001, 34, 167.

[19] [19] Chikhalia, K. H.; Vashi, D. B.; Patel, M. J. J. Enz. Inhi. & Med. Chem. 2009, 24, 617.

[20] [20] Nag, S.; Pathak, R.; Kumar, M.; Shukla, P. K.; Batra, S. Bioorg. Med. Chem. Lett. 2006, 16, 3824.

[21] [21] Taylor, A. E.; Terry, R. J.; Godfrey, D. G. Brit. J. Pharmacol. Chemother. 1956, 11, 71.

[22] [22] Frey, R. R.; Curtin, M. L.; Albert, D. H.; Glaser, K. B.; Pease, L. J.; Soni, N. B.; Marcotte, P.; Bukofzer, G.; Li, J.; Davidsen, S. K.; Michaelides, M. R. J. Med. Chem. 2008, 51, 3777.

[23] [23] Easmon, J.; Purstinger, G.; Heinisch, G.; Roth, T.; Fiebig,H. H.; Holzer, W.; Jager, W.; Jenny, M.; Hofmann, J. J. Med. Chem. 2001, 44, 2164.

[24] [24] Campiani, G.; Fabbrini, M.; Morelli, E.; Nacci, V; Greco, G.; Novellino, E.; Bergamini, A.; Faggioli, E.; Uccella, I.; Bolacchi, F.; Marini, S.; Coletta, M.; Fracasso, C.; Caccia,S. Antiviral Chem. Chemother. 2000, 11, 141.

[25] [25] Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyter, J.; De Clercq, E. J. Virol. Methods. 1988, 20, 309.

[26] [26] Bruckner, H.; Strecker, B. J. Chromatogr. 1992, 627, 97.

Abstract

References

Similar Articles

Most read articles by the same author(s)