Synthesis, Characterization, Aggregation behaviors, Antioxidant and Anti-inflammatory activities of Unmetalled and metallophthalocyanines bearing 2(3,4-dimethoxyphenyl)ethanol and 4-Hydroxybenzaldehyde groups
Abstract
Novel metallophthalocyanines (M: Co, Cu, Ni) containing 2(2-methoxyphenyl)ethanol and 3-Hydroxybenzaldehyde groups were synthesized and characterized.
The structures were confirmed by IR, UV/vis, 1H NMR, 13C NMR, mass spectroscopy  and elemental analysis. The aggregation behavior of these compounds was investigated in DMSO. In addition; the compounds 4-9 were investigated for anti-oxidant activities by super oxide radical; DPPH (2,2-Diphenyl-1-picrylhydrazyl); and hydroxyl radical scavenging assays; in which most of them displayed significant antioxidant activities. Furthermore; compounds 4-9  were evaluated for anti-inflammatory activity by indirect hemolytic and lipoxygenase inhibition assays and revealed good activity.
Full Text:
PDFReferences
- N.B. McKeown, Phthalocyanine Materials: Synthesis, Structure and Function; Cambridge University Press:Cambridge, UK, 1998.
- C.C. Lezno, A.B.P. Lever, Phthalocyanines: Properties and Applications; VCH Publishers: New York, NY, USA, 1996.
- P.J. Gregory, Porphyr. Phthalocya. 2000, 4, 432-437.
- J. Simon, C. Sirlin, Pure Appl. Chem. 1989, 61, 1625-1629.
- H. Yanaji, N. Tamura, S. Taira, H. Furuda, S. Douko, G. W. Schnupfeil, D. Ohrle, Mol. Cryst. Liq. Cryst Sci.Technol. Sect. A 1995, 267, 435-440.
- M.J.F. Calvete, D. Dini, S.R. Flom, M. Hanack, R.G.S. Pong, J.S. Shirk, Eur. J. Org. Chem. 2005, 16, 3499-3509.
- J.J. Cid, J.H. Yum, S.R. Jang, M.K. Nazeeruddin, E. Martinez-Ferrero, E. Palomares, J. Ko, M. Gratzel, T. Torres, Angew. Chem. Int. Edit. 2007, 119, 8510-8514.
- E.J. Osburn, L.K. Chau, S.Y. Chen, N. Collins, D.F. O'Brien, N.R. Armstrong, Langmuir 1996, 12, 4784-4796.
- A. Kalkan, Z.A. Bayer, Polyhedron 2006, 25, 39-42.
- A.K. Burat, A. Koca, J.P. Lewtak, D.T. Gryko, Synthetic Met. 2011, 161, 1537-1545.
- A. Atsay, A. Gul, M.B. Koçak, Dyes Pigments 2014, 100, 177-183.
- A.Y. Shen, S.N. Wu, C.T.J. Chiu, Pharm. Pharmacol. 1999, 51, 543–548
- I. Acar, S.M. Durmu, H.J. Kantekin, Organomet. Chem. 2012, 708, 65-74.
- G. Scott, Antioxidants in science, technology, medicine and nutrition. 1997, Coll house, Albion Publishing.
- M. Simic, M. Karel, Autoxidation in food and biological systems. 1980, Plenum Press, New York.
- B.L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Matthews, NC, USA, 2002.
- T. Fukuda, T. Ishiguro, N. Kobayashi, Tetrahedron Lett. 2005, 46, 2907-2909.
- N. Kobayashi, T. Fukuda, K. Ueno, H. Ogino, J. Am. Chem. Soc., 2001, 123, 10740-10741.
- W. Wu, S. Ji, H. Guo, X. Wang, J. Zhao, Dyes Pigments 89, 2011, 199-211.
- S. Altun , A. Altındal , M. Bulut, Polyhedron 49, 2013, 41-4.9
- Y. Gök, H. Kantekin, M.B. Kılıc¸ aslan, H. Alp, Dyes and Pigments 74, 2007, 692-698.
- H.A. Dinçer, A. Gül, M.B. Koc¸ ak, Journal of Porphyrins and Phthalocyanines 8, 2004, 1204-1208.
- D.D. Dominguez, A.W. Snow, J.S. Shirk, P.S. Pong, J. Porphyrins Phthalocyanines, 2001, 582.
- M.N. Yarasır, M. Kandaz, B.F. Senkal, A. Koca, B. Salih, Polyhedron 26, 2007, 5235.
- M. Barthel, D. Dini, S. Vagin, M. Hanack, Eur. J. Org. Chem. 3756, 2002, 3762.
- Y. ArslanoÄŸlu, E. Hamuryudan, Dyes and Pigments 75, 2007, 150-155.
- Y.M.D. Chuanga, Y.S. Wanga, Y.Y. Kuob, H.P. Tsaia, W.L. Shyura, J. Ethnopharmacol., 95, 2004, 409-419.
- D.D. Dominguez, A.W. Snow, J.S. Shirk, P.S. Pong, J. Porphyrins Phthalocyanines, 5, 2001, 582.
- M.N. Yarasır, M. Kandaz, B.F. Senkal, A. Koca, B. Salih, Polyhedron 26, 2007, 5235.
- U.A. Shinde, K.R. Kulkarni, A.S. Phadke, A. M. Nair, D.V.J. Mungantiwar, M.N. Saraf, Ind. J. Exp. Biol., 371, 1999, 258-261.
- H.G. Boman, U. Kaletta, Biochem. Biophys. Acta., 24, 1957, 619- 623.
- K.H. Ahn, H. Kim, J.R. Kim, S.C. Jeomg, T.S. Kang, H.T. Shin, G.J. Lim, Bull. Korean Chem. Soc., 23, 2002, 626-628.
DOI: http://dx.doi.org/10.13171/mjc56/01607261513/alayed
Refbacks
- There are currently no refbacks.
Copyright (c) 2016 Mediterranean Journal of Chemistry