Journal of Chemistry
9
gram negative E. coli (25822) and P. aeruginosa (27583)]
showed no activity; this might be due to the poor solubility
and precipitation during the dilution process.
[6] Z. Nie, C. Perretta, P. Erickson et al., “Structure-based design,
synthesis, and study of pyrazolo[1,5-a][1,3,5]triazine derivatives
as potent inhibitors of protein kinase CK2,” Bioorganic and
Medicinal Chemistry Letters, vol. 17, no. 15, pp. 4191–4195, 2007.
[7] Z. Nie, C. Perretta, P. Erickson et al., “Structure-based design
and synthesis of novel macrocyclic pyrazolo[1,5-a] [1,3,5]tri-
azine compounds as potent inhibitors of protein kinase CK2
and their anticancer activities,” Bioorganic and Medicinal Chem-
istry Letters, vol. 18, no. 2, pp. 619–623, 2008.
[8] V. K. Pandey, S. Tusi, Z. Tusi, M. Joshi, and S. Bajpai, “Synthesis
and biological activity of substituted 2,4,6-s-triazines,” Acta
Pharmaceutica, vol. 54, no. 1, pp. 1–12, 2004.
[9] A. Agarwal, K. Srivastava, S. K. Puri, and P. M. S. Chauhan,
“Synthesis of substituted indole derivatives as a new class of
antimalarial agents,” Bioorganic and Medicinal Chemistry Let-
ters, vol. 15, no. 12, pp. 3133–3136, 2005.
[10] W. Zhu, Y. Liu, Y. Zhao et al., “Synthesis and biological evalu-
ation of novel 6-hydrazinyl-2,4-bismorpholino pyrimidine and
1,3,5-triazine derivatives as potential antitumor agents,” Archiv
der Pharmazie, vol. 345, no. 10, pp. 812–821, 2012.
[11] V. R. Avupati, R. P. Yejella, V. R. Parala et al., “Synthesis, charac-
terization and in vitro biological evaluation of some novel 1,3,5-
triazine-Schiff base conjugates as potential antimycobacterial
agents,” Bioorganic and Medicinal Chemistry Letters, vol. 23, no.
21, pp. 5968–5970, 2013.
[12] H. H. Al-Rasheed, M. Al Alshaikh, J. M. Khaled, N. S. Alharbi,
and A. El-Faham, “Ultrasonic irradiation: synthesis, character-
ization, and preliminary antimicrobial activity of novel series
of 4,6-disubstituted-1,3,5-triazine containing hydrazone deriva-
tives,” Journal of Chemistry, vol. 2016, Article ID 3464758, 9
pages, 2016.
4. Conclusion
Reaction of 2-hydrazino-2,6-disubstituted-1,3,5-triazine with
5-acetyl-1,3-dimethyl barbituric acid in ethanol affords the
hydrazine derivatives in the enhydrazine form as a pure
isomer rather than the hydrazone form as observed from the
spectral data. e geometry optimization was done by DFT
method using B3LYP/6-31G∗∗ to calculate the relative energy
of the three structures 5b-A, 5b-B, and 5b-C and indicated
that the enhydrazine 5b-B is the most stable structure while
5b-A and 5b-C are less stable which agrees with the NMR
spectral data. Although no significant activity of the first
family of these compounds has been found as antibacterial,
more derivatives are being prepared for overcoming the
solubility problems, which are believed to be the cause of the
poor biological activity.
Additional Points
Supporting Information. H NMR, 13C NMR spectra, and
HRMS for the prepared compounds will be available online
in Supplementary Material.
1
Conflicts of Interest
e authors declare no conflicts of interest.
[13] H. Singh, L. D. S. Yadav, K. N. Shukla, and R. Dwivedi, “Synthe-
sis of new 1,3,4-oxadiazolo [3, 2-a]-s-triazine-5,7-dithiones and
the dithionone analogues as potential antifungal agents,” Indian
Journal of Pharmaceutical Sciences, vol. 54, no. 1, pp. 33–37, 1992.
Acknowledgments
e authors thank the International Scientific Partnership
Program ISPP at King Saud University (ISPP# 0061) (Saudi
Arabia). e research at South Africa was funded by National
Research Foundation (NRF) and the University of KwaZulu-
Natal.
[14] M. Jarman, H. M. Coley, I. R. Judson et al., “Synthesis and cyto-
toxicity of potential tumor-inhibitory analogues of trimelamol
(2,4,6-Tris[(hydroxymethyl)methylamino]-1,3,5-triazine) hav-
ing electron-withdrawing groups in place of methyl,” Journal of
Medicinal Chemistry, vol. 36, no. 26, pp. 4195–4200, 1993.
[15] A. Dhainaut, G. Re´gnier, G. Atassi et al., “New triazine deriva-
tives as potent modulators of multidrug resistance,” Journal of
Medicinal Chemistry, vol. 35, no. 13, pp. 2481–2496, 1992.
References
[16] D. C. Tahmassebi and T. Sasaki, “Synthesis of a three-helix
bundle protein by reductive amination,” Journal of Organic
Chemistry, vol. 63, no. 3, pp. 728–731, 1998.
[17] J. Y. Lee, M. E. Brune, R. B. Warner et al., “Antihypertensive
activity of ABBOTT-81282, a nonpeptide angiotensin II antag-
onist, in the renal hypertensive rat,” Pharmacology, vol. 47, no.
3, pp. 176–187, 1993.
[18] L. Brunton, J. Lazo, and K. G. Parker, Gilman’s e Pharmaco-
logical Basis of erapeutics, Mc Graw-Hill, New York, NY, USA,
11th edition, 2005.
[1] D. R. Shah, R. P. Modh, and K. H. Chikhalia, “Privileged s-tri-
azines: structure and pharmacological applications,” Future
Medicinal Chemistry, vol. 6, no. 4, pp. 463–477, 2014.
[2] R. Kumar, A. D. Singh, J. Singh, H. Singh, R. K. Roy, and
A. Chaudhary, “1,2,3-triazine scaffold as a potent biologically
active moiety: a mini review,” Mini-Reviews in Medicinal Chem-
istry, vol. 14, no. 1, pp. 72–83, 2014.
[3] J. P. Raval, A. R. Rai, N. H. Patel, H. V. Patel, and P. S. Patel,
“Synthesis and in vitro antimicrobial activity of N’-(4-(arylam-
ino)-6-(pyridin-2-ylamino)-1,3,5-triazin-2-yl)benzohydrazide,”
International Journal of ChemTech Research, vol. 3, no. 1, pp.
616–620, 2009.
[1
9] M. W. Johns, “Sleep and hypnotic drugs,” Drugs, vol. 9, no. 6, pp.
448–478, 1975.
[20] S. R. Whittle and A. J. Turner, “Differential effects of sedative
and anticonvulsant barbiturates on specific [3H]GABA binding
to membrane preparations from rat brain cortex,” Biochemical
Pharmacology, vol. 31, no. 18, pp. 2891–2895, 1982.
[21] H. Brunner, K.-P. Ittner, D. Lunz, S. Schmatloch, T. Schmidt, and
M. Zabel, “Highly enriched mixtures of methohexital stereoiso-
mers by palladium-catalyzed allylation and their anaesthetic
[4] S. Nishigaki, F. Yoneda, H. Matsumoto, and K. Morinaga, “Syn-
thetic antibacterials. I. Nitrofurylvinyl-s-triazine derivatives,”
Journal of Medicinal Chemistry, vol. 12, no. 1, pp. 39–42, 1969.
[5] D. H. Mahajan, C. Pannecouque, E. De Clercq, and K. H. Chi-
khalia, “Synthesis and studies of new 2-(coumarin-4-yloxy)-
4,6-(substituted)-S-triazine derivatives as potential anti-HIV
agents,” Archiv der Pharmazie, vol. 342, no. 5, pp. 281–290, 2009.