Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2017, Article ID 1509129, 7 pages
https://doi.org/10.1155/2017/1509129
Research Article

One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

1Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia
2Centre for Pre-University Studies, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia

Correspondence should be addressed to Zainab Ngaini; ym.saminu@baniazn

Received 15 March 2017; Revised 21 April 2017; Accepted 23 April 2017; Published 3 July 2017

Academic Editor: Liviu Mitu

Copyright © 2017 Zainab Ngaini et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. P. K. Mohanta, S. Dhar, S. K. Samal, H. Ila, and H. Junjappa, “1-(Methyldithiocarbonyl)imidazole: A useful thiocarbonyl transfer reagent for synthesis of substituted thioureas,” Tetrahedron, vol. 56, no. 4, pp. 629–637, 2000. View at Publisher · View at Google Scholar · View at Scopus
  2. N. Sun, B. Li, J. Shao et al., “A general and facile one-pot process of isothiocyanates from amines under aqueous conditions,” Beilstein Journal of Organic Chemistry, vol. 8, pp. 61–70, 2012. View at Publisher · View at Google Scholar · View at Scopus
  3. A. Saeed, N. Abbas, H. Rafique, S. Rashid, and A. Hameed, “Synthesis, characterization and antibacterial activity of some 1-aroyl-3-aryl thiourea,” Chemistry, vol. 18, no. 5, pp. 152–158, 2009. View at Google Scholar
  4. N. A. Nordin, T. W. Chai, B. L. Tan et al., “Novel synthetic monothiourea aspirin derivatives bearing alkylated amines as potential antimicrobial agents,” Journal of Chemistry, vol. 2017, no. 1, pp. 1–7, 2017. View at Publisher · View at Google Scholar
  5. M. K. Rauf, Imtiaz-ud-Din, A. Badshah et al., “Synthesis, structural characterization and in vitro cytotoxicity and anti-bacterial activity of some copper (I) complexes with N, N′-disubstituted thioureas,” Journal of Inorganic Biochemistry, vol. 103, no. 8, pp. 1135–1144, 2009. View at Publisher · View at Google Scholar · View at Scopus
  6. W. S. H. Wan Zullkiplee, A. N. Abd Halim, Z. Ngaini, M. A. Mohd Ariff, and H. Hussain, “Bis-Thiourea bearing aryl and amino acids side chains and their antibacterial activities,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 189, no. 6, pp. 832–838, 2014. View at Publisher · View at Google Scholar · View at Scopus
  7. A. N. Abd Halim and Z. Ngaini, “Synthesis and bacteriostatic activities of bis (thiourea) derivatives with variable chain length,” Journal of Chemistry, vol. 2016, no. 1, pp. 1–7, 2016. View at Publisher · View at Google Scholar
  8. W. S. H. Wan Zullkiplee, M. A. Mohd Ariff, H. Hussain, W. M. Khairul, and Z. Ngaini, “Bacteriostatic activities of N-substituted tris-thioureas bearing amino acid and aniline substituents,” Phosphorus, Sulfur and Silicon and the Related Elements, pp. 1–5, 2016. View at Publisher · View at Google Scholar · View at Scopus
  9. W. Fathalla, M. Čajan, J. Marek, and P. Pazdera, “One-pot quinazolin-4-yl-thiourea synthesis via N-(2-cyanophenyl)benzimidoyl isothiocyanate,” Molecules, vol. 6, no. 7, pp. 588–602, 2001. View at Publisher · View at Google Scholar · View at Scopus
  10. N. Azizi, A. Khajeh-Amiri, H. Ghafuri, and M. Bolourtchian, “Toward a practical and waste-free synthesis of thioureas in water,” Molecular Diversity, vol. 15, no. 1, pp. 157–161, 2011. View at Publisher · View at Google Scholar · View at Scopus
  11. K. Appalanaidu, T. Dadmal, N. Jagadeesh Babu, and R. M. Kumbhare, “An improved one-pot multicomponent strategy for the preparation of thiazoline, thiazolidinone and thiazolidinol scaffolds,” RSC Advances, vol. 5, no. 107, pp. 88063–88069, 2015. View at Publisher · View at Google Scholar · View at Scopus
  12. V. Štrukil, M. D. Igrc, L. Fábián et al., “A model for a solvent-free synthetic organic research laboratory: Click-mechanosynthesis and structural characterization of thioureas without bulk solvents,” Green Chemistry, vol. 14, no. 9, pp. 2462–2473, 2012. View at Publisher · View at Google Scholar · View at Scopus
  13. H. R. Allcock, J. S. Rutt, and M. Parvez, “Synthesis of cyclic phosphazenes with isothiocyanato, thiourethane, and thiourea side groups: X-ray crystal structure of N3P3(NMe2)3(NCS)3,” Inorganic Chemistry, vol. 30, no. 1, pp. 1776–1782, 1991. View at Publisher · View at Google Scholar · View at Scopus
  14. Z. Ngaini and N. I. A. Rahman, “Synthesis and characterization of chalconesubstituted phosphazenes,” Canadian Journal of Chemistry, vol. 88, no. 7, pp. 654–658, 2010. View at Publisher · View at Google Scholar · View at Scopus
  15. Z. Ngaini and N. I. A. Rahman, “Synthesis and characterization of cyclotriphosphazenes bearing chalcones derivatives,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 185, no. 3, pp. 628–633, 2010. View at Publisher · View at Google Scholar · View at Scopus
  16. R. K. Voznicová, J. Taraba, J. Příhoda, and M. Alberti, “The synthesis and characterization of new aminoadamantane derivatives of hexachloro-cyclo-triphosphazene,” Polyhedron, vol. 27, no. 9-10, pp. 2077–2082, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. Z. Ngaini, M. A. Mohd Arif, H. Hussain, E. S. Mei, D. Tang, and D. H. A. Kamaluddin, “Synthesis and antibacterial activity of acetoxybenzoyl thioureas with aryl and amino acid side Chains,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 187, no. 1, pp. 1–7, 2012. View at Publisher · View at Google Scholar · View at Scopus
  18. P. Venkatesh and S. N. Pandeya, “Synthesis, characterisation and anti-inflammatory activity of some 2-amino benzothiazole derivatives,” International Journal of ChemTech Research, vol. 1, no. 4, pp. 1354–1358, 2009. View at Google Scholar · View at Scopus
  19. R. L. Smith and R. T. Williams, “The metabolism of arylthioureas - IV. p-chorophenyl- and p-tolyl-thiourea,” Journal of Medicinal and Pharmaceutical Chemistry, vol. 4, no. 1, pp. 147–162, 1961. View at Publisher · View at Google Scholar · View at Scopus
  20. National Center for Biotechnology Information, PubChem Compound Database, Apr 2017, CID = 3040094, https://pubchem.ncbi.nlm.nih.gov/compound/3040094.
  21. N. B. Pappano, O. P. Centorbi, and F. H. Ferretti, “Determination of minimum concentration inhibitory chalcone derivatives,” Revise Microbiology, vol. 2, no. 1, pp. 183–188, 1990. View at Google Scholar
  22. O. Trott and A. J. Olson, “AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading,” Journal of Computational Chemistry, vol. 31, no. 2, pp. 455–461, 2010. View at Publisher · View at Google Scholar
  23. G. M. Morris, H. Ruth, W. Lindstrom et al., “Software news and updates AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility,” Journal of Computational Chemistry, vol. 30, no. 16, pp. 2785–2791, 2009. View at Publisher · View at Google Scholar · View at Scopus
  24. S. George, M. B. Ramzeena, S. V. Ram, S. K. Selvaraj, S. Rajan, and T. K. Ravi, “Design, docking, synthesis and anti E. coli screening of novel thiadiazolo thiourea derivatives as possible inhibitors of enoyl ACP reductase (FabI) enzyme,” Bangladesh Journal of Pharmacology, vol. 9, no. 1, pp. 49–53, 2014. View at Publisher · View at Google Scholar · View at Scopus
  25. Y. K. Shao and J. X. Si, “Synthesis and herbicidal activity of N-(o-flourophenoxyacetyl) thiourea activities and related fused heterocyclic compound,” Arkivoc, vol. 10, pp. 63–68, 2006. View at Google Scholar
  26. K. Moriya, T. Masuda, T. Suzuki, S. Yano, and M. Kajiwara, “Liquid crystalline phase transition in hexakis (4-(n-(41-alkoxyphenyl) iminomethyl) phenoxy) cyclotriphosphazene,” Molecular Crystals and Liquid Crystals, vol. 318, no. 1, pp. 267–278, 1998. View at Publisher · View at Google Scholar · View at Scopus
  27. E. Cil, M. Arslan, and A. O. Gorgulu, “Synthesis and characterisationof benzyl andbenzoyl substituted oxime-phosphazees,” Polyhedron, vol. 25, no. 18, pp. 3526–3532, 2006. View at Publisher · View at Google Scholar
  28. G. G. Muccioli, J. Wouters, G. K. E. Scriba, W. Poppitz, J. H. Poupaert, and D. M. Lambert, “1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: New templates among the CB1 cannabinoid receptor inverse agonists,” Journal of Medicinal Chemistry, vol. 48, no. 23, pp. 7486–7490, 2005. View at Publisher · View at Google Scholar · View at Scopus
  29. Y.-H. Shen and D.-J. Xu, “Phenylthiourea,” Acta Crystallographica Section E: Structure Reports Online, vol. 60, no. 7, pp. o1193–o1194, 2004. View at Publisher · View at Google Scholar · View at Scopus
  30. R. S. Corrêa, O. Estévez-Hernández, J. Ellena, and J. Duque, “1-(2-Furoyl)-3-(o-tolyl)thiourea,” Acta Crystallographica Section E: Structure Reports Online, vol. 64, no. 8, p. o1414, 2008. View at Publisher · View at Google Scholar · View at Scopus
  31. H. R. Allcock, Phosphorus-Nitrogen Compounds: Cyclic, Linear, and High Polymeric Systems, Academic Press, Elsevier, New York, NY, USA, 1972.
  32. M. De Los Angeles Alvarez, V. E. P. Zarelli, N. B. Pappano, and N. B. Debattista, “Bacteriostatic action of synthetic polyhydroxylated chalcones against Escherichia coli,” Biocell, vol. 28, no. 1, pp. 31–34, 2004. View at Google Scholar · View at Scopus
  33. H. Arslan, N. Duran, G. Borekci, C. K. Ozer, and C. Akbay, “Antimicrobial activity of some thiourea derivatives and their nickel and copper complexes,” Molecules, vol. 14, no. 1, pp. 519–527, 2009. View at Publisher · View at Google Scholar · View at Scopus
  34. J. L. Ramos, S. Marqués, and K. N. Timmis, “Transcriptional control of the Pseudomonas TOL plasmid catabolic operons is achieved through an interplay of host factors and plasmid-encoded regulators,” Annual Review of Microbiology, vol. 51, pp. 341–373, 1997. View at Publisher · View at Google Scholar · View at Scopus
  35. P.-C. Lv, H.-Q. Li, J. Sun, Y. Zhou, and H.-L. Zhu, “Synthesis and biological evaluation of pyrazole derivatives containing thiourea skeleton as anticancer agents,” Bioorganic and Medicinal Chemistry, vol. 18, no. 13, pp. 4606–4614, 2010. View at Publisher · View at Google Scholar · View at Scopus
  36. N. K. N. A. Zawawi, M. Taha, N. Ahmat et al., “Synthesis, in vitro evaluation and molecular docking studies of biscoumarin thiourea as a new inhibitor of α-glucosidases,” Bioorganic Chemistry, vol. 63, pp. 36–44, 2015. View at Publisher · View at Google Scholar · View at Scopus
  37. E. Tatar, S. Karakuş, S. G. Küçükgüzel et al., “Design, synthesis, and molecular docking studies of a conjugated thiadiazole–thiourea scaffold as antituberculosis agents,” Biological and Pharmaceutical Bulletin, vol. 39, no. 4, pp. 502–515, 2016. View at Publisher · View at Google Scholar · View at Scopus
  38. M. Meyer, P. Wilson, and D. Schomburg, “Hydrogen bonding and molecular surface shape complementarity as a basis for protein docking,” Journal of Molecular Biology, vol. 264, no. 1, pp. 199–210, 1996. View at Publisher · View at Google Scholar · View at Scopus
  39. S. Purser, P. R. Moore, S. Swallow, and V. Gouverneur, “Fluorine in medicinal chemistry,” Chemical Society Reviews, vol. 37, no. 2, pp. 320–330, 2008. View at Publisher · View at Google Scholar · View at Scopus
  40. Y. He, Y. Wang, L. Tang et al., “Binding of puerarin to human serum albumin: a spectroscopic analysis and molecular docking,” Journal of Fluorescence, vol. 18, no. 2, pp. 433–442, 2008. View at Publisher · View at Google Scholar · View at Scopus