Synthesis and characterization of mixed Amides-Imines and Amides-Azo Compound derived from Chrysanthemic acid and trimethoprim and study their biological activities | ||
| Journal of University of Anbar for Pure Science | ||
| Article 6, Volume 11, Issue 1, April 2017, Pages 14-22 PDF (719.01 K) | ||
| Document Type: Research Paper | ||
| DOI: 10.37652/juaps.2017.141527 | ||
| Authors | ||
| Mohammad F. Mesher1; Barram A. Hama2; Balqes A. Ahmed1 | ||
| 1College of Science, University of Anbar | ||
| 2Collage of Science, University of Sulaimanih. | ||
| Abstract | ||
| Chrysanthemic acid, Trimethoprim, amides, Imines and azo compound : all found to have enormous biological activities in different directions such as medical , pharmaceutical pesticidal …etc. Accordingly combination of these functional in on compound expected to enhances their activities. Therefore mixed amides – imines and amides – diazo derived from trimethoprim and chrysanthemic acid, have been prepared by reaction of equimolar amount of these compound to form the corresponding mono amides , which on treatment of the remaining amino group of the trimethoprim with some aromatic aldehydes give the corresponding imines ; or diazo compounds on reaction with nitrous acid followed by reaction with aromatic phenols and naphthols . The structures of these derivatives were confirmed by their physical properties and spectroscopic techniques such as FT-IR ; 1Hnmr and mass spectrometry for selected compound. In addition the biological evaluation of the synthesized compound have been studied through the investigation of its capacity to scavenge the free radical (DPPH.) to give an inhibition at 50% concentration (IC50) , using the butylated hydroxyl toluene (BHT) as a control. This study reveals the highest scavenging for the azo derivatives . | ||
| Keywords | ||
| Chrysanthemic acid; trimethoprim; Imines; Amides; azo compound | ||
| References | ||
|
1- J. DeRuiter "Amides and related functional groups" Principles of Drug Action 1, Spring, ( 2005).
2- C. M. Crudden, Y. B. Hleba and A. C. Chen, Journal of the American Chemical Society, 126, 9200, (2004).
3- Y. Lee and A. H. Hoveyda, Journal of the American Chemical Society, 131,3160, (2009).
4- A. Patchett, E. Harris, E. Tristram, M. Wyvratt and D. Taub "A new class of angiotensin-converting enzyme inhibitors" Journal of Medical Chemistry, (1980).
5- E. O'Connor Stephen, A. Grosset and P. Ja niak " The pharmacological basis and pathophysiological significance of the heart rate-lowering property of diltiazem" Fundamental and Clinical Pharmacology, (13), 145–153, (1999).
6- W. Andre, F. Iduna, S. Gretel and K. Felix " Synthesis, Cleavage Profile and antitumor efficacy of anAlbumin- Binding Prodrug of Methotrexate that is cleaved by Plasmin and Cathepsine B" Chemistry in Life Sciences, (8), 389-95, (2007).
7- M. Mihaela, S. Valeriu, P. Lenuta, P. Marcel and L. Catalina "Synthesis and antimicrobial activity of some new (sulfonamidophenyl)-amide derivatives of N-(4- nitrobenzoyl)-Phenylalanine" Farmaica, (2008).
8- C. Liana Allen " Catalytic Approaches to the Synthesis of Amid Bonds" A thesis submitted for the degree of Doctor of Philosophy University of Bath, (2012).
9- S.A. Naman, A.H. Jassim and . M.F. Alias, Journal of Photochemistry and Photobiology A: Chemistry,41, 150,(2002).
10- R.V. Hoffma "Organic chemistry anintermediate text " Inc.America, 315,(2004).
11- C. Parkanyi and D.S. Schmidt, Journal of Hetrocyclic Chemistry,37, 725, (2002).
12- M. Wang, K. Funabiki and M. Matsu "Synthesis and properties of bis(hetaryl)azo dyes" Dyes and Pigments, (57), 77–86, (2003).
13- C.M.L. Delpiccolo and E.G. Mata "Tetrahedron: Asymmetry" (13), 905-910, (2002).
14- A.H. Manikshete and S.K.Sarsamkar " Synthesis and characterization of divalent transition metal complexes of Schiff bases derived from benzoin and 4-amino benzoic acid" WalchandCollege ofArts and Science, Solapur,Maharashtra, (3), 105-111, (2010).
15- V. Babu, P. Harinadha, K. Senthil, and G. Bhat "Synthesis, Antitumor and Antibacterial Activies of certain Substituted Pyrimidines Bearing Benzofuran" Indian Journal of Pharmaceutical Sciences, (5), 647-652, (2004).
16- Sh. Elroby and S.U. Aziz ''Understanding the decomposition reaction mechanism of chrysanthemic acid: a computational study'' Chemistry Central Journal, (1), (2011).
17- H. Yoshioka and J. Miyamoto ''Synthetic Pyrethroids (1)'' Chemical Biology, 427–434, (1976).
18- H. Staudinger and L. Ruzicka ''Insektento¨tende Stoffe I: u¨ber Isolierung und Konstitution des wirksamen Teiles des dalmatinisc'' Helvetica Chimica Acta,(7), 177–259, (1924).
19- F. Lafferty " Turecek. Interpretain of Mass Spectra" 4th edn., California, Mill Valley, University Science Books, 371, (1993).
20- M.A. Esmaeili, A. Sonboli and M.A. Noshabadi "Antioxidant and protective properties of six Tanacetum species against hydrogen peroxide-induced oxidative stress in K562 cell line: A comparative study" Food Chemistry, (1), 148-55, (2010). | ||
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