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Salicylic acid derivatives: synthesis, features and usage as therapeutic tools

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Pages 1831-1841 | Published online: 20 Nov 2011

Bibliography

  • Raskin I. Salicylate, a new plant hormone. Plant Physiol 1992;99:799-803
  • Mitchell AG, Broadhead JF. Hydrolysis of solubilized aspirine. J Pharm Sci 1967;21:1261-6
  • Raskin I, Skubatz H, Tang W, Salicylic acid levels in thermogenic and nonthermogenic plants. Ann Bot 1990;66:376-83
  • Hassan GS, Soliman GA. Design, synthesis and anti-ulcerogenic effect of some of furo-salicylic acid derivatives on acetic acid-induced ulcerative colitis. Eur J Med Chem 2010;45:4104-12
  • Jung Y, Kim HH, Kim H, Evaluation of 5aminosalicytaurine as a colon-specific prodrug of 5-aminosalicylic acid for treatment of experimental colitis. Eur J Pharm Sci 2006;28:26-33
  • Nielsen OH, Munck LK. Drug insight: aminosalicylates for treatment of IBD. Nat Clin Pract Gastroenterol Hepatol 2007;4:160-70
  • Varshosaz J, Emami J, Tavakoli N, Synthesis and evaluation of dextran-budesonide conjugates as colon specific prodrugs for treatment of ulcerative colitis. Int J Pharm 2009;365:69-76
  • El-Matary W, Vandermeer B, Griffiths AM. Methotrexate for maintenance of remission in ulcerative colitis. Cochrane Database Syst Rev 2009;3:CD007560
  • Eshuis EJ, Bemelman WA, Stokkers PC. Infliximab for the treatment of ulcerative colitis. Expert Rev Gastroenterol Hepatol 2009;3:219-29
  • Mayberry H, Moshkoyska T, Mayberry JF. Co-prescribing azathiopurine or 6 mercaptopurine and 5-aminosalicylate compounds in ulcerative colitis. Inflamm Bowel Dis 2009;15:190-2
  • Joeres-Nquyen-Xuan TH, Boehm SK, Joeres L, Survival of the probiotic Escherichia coli Nissle 1917 (EcN) in the gastrointestinal tract given in combination with oral mesalamine to healthy volunteers. Inflamm Bowel Dis 2010;16:256-62
  • Actis GC, Pazienza P, Rosina F. Mesalamine for inflammatory bowel disease: recent reappraisals. Inflamm Allergy Drug Targets 2008;7:1-5
  • Jain A, Gupta Y, Jain SK. Azo chemistry and its potential for colonic delivery. Crit Rev Ther Drug Carrier Syst 2006;23:349-400
  • Patil SA, Moss AC. Balsalazide disodium for the treatment of ulcerative colitis. Expert Rev Gastroenterol Hepatol 2008;2:177-84
  • Dhaneshwar SS, Chail M, Patil M, Colon-specific mutal prodrugs of 4-aminosalicylic acid for their mitigating effect on experimental colitis in rats. Eur J Med Chem 2009;44:131-42
  • Luchini AC, Rodriques-Oris P, Cestari SH, Intestinal anti-inflammatory activity of coumarin and 4-hydroxycoumarin in the trinitrbenzenesulphonic acid model of rat colitis. Biol Pharm Bull 2008;31:1343-50
  • Deore V, Yewalkar N, Bhatia D, Synthesis and therapeutic evaluation of pyridyl based novel mTOR inhibitors. Bioorg Med Chem Lett 2009;19:2949-52
  • Hassan GS, Soliman GA. Design, synthesis and anti-ulcerogenic effect of some of furo-salicylic acid derivatives on acetic acid-induced ulcerative colitis. Eur J Med Chem 2010;45:4104-12
  • Boutaud O, Oates JA. Study of inhibitors of the PGH synthases for which potency is regulated by the redox state of the enzymes. Methods Mol Biol 2010;644:67-90
  • Howardell MJ. COX-2 Inhibitor Research. Nova Science Publishers, Inc; (NY), USA: 2006. p. 1-236
  • Jadhav V, Jabre A, Chen MF, Presynaptic prostaglandin E-2 EP1-Receptor facilitation of cerebral nitrergic neurogenic vasodilation. Stroke 2009;40:261-9
  • Jamshidi F, Zhang J, Harrison JS, Induction of differentiation of human leukemia cells by combinations of COX inhibitors and 1,25-dihydroxyvitamin D-3 involves Raf1 but not Erk 1/2 signaling. Cell Cycle 2008;7:917-24
  • Burke A, Smyth E, FitzGerald G. Chapter 26: Analgesic Antipyretic and Antiinflammatory Agents in Goodman and Gilman's the pharmacological basis of therpeutics. McGraw-Hill; New York: 2006. p. 671-716
  • Durdagi S, Senturk M, Ekinci D, Kinetic and docking studies of phenol-based inhibitors of carbonic anhydrase isoforms I, II, IX and XII evidence a new binding mode within the enzyme active site. Bioorg Med Chem 2011;19:1381-9
  • Ceyhun SB, Senturk M, Ekinci D, Deltamethrin attenuates antioxidant defense system and induces the expression of heat shock protein 70 in rainbow trout. Comp Biochem Phys Chem 2010;152:215-23
  • Ekinci D, Ceyhun SB, Aksakal E, Erdogan O. IGF. and GH mRNA levels are suppressed upon exposure to micromolar concentrations of cobalt and zinc in rainbow trout white muscle. Comp Biochem Phys Chem 2011;153:336-41
  • Erdogan O, Ceyhun SB, Ekinci D, Aksakal E. Impact of deltamethrin exposure on mRNA expression levels of metallothionein A, B and cytochrome P450 1A in rainbow trout muscles. Gene 2011;484:13-17
  • Cakmak R, Durdagi S, Ekinci D, Design, synthesis and biological evaluation of novel nitroaromatic compounds as potent glutathione reductase inhibitors. Bioorg Med Chem Lett 2011;21:5398-402
  • Aksakal E, Ekinci D, Erdogan O, Increasing stocking density causes inhibition of metabolic-antioxidant enzymes and elevates mRNA levels of heat shock protein 70 in rainbow trout. Livest Sci 2011;141:69-75
  • Siktar E, Ekinci D, Siktar E, Protective role of L-carnitine supplementation against exhaustive exercise-induced oxidative stress in rats. Eur J Pharmacol 2011;668:407-13
  • Ceyhun SB, Senturk M, Yerlikaya E, Purification and characterization of carbonic anhydrase from the teleost fish Dicentrarchus labrax (European Seabass) liver and toxicological effects of metals on enzyme activity. Environ Toxicol Pharmacol 2011;32:69-74
  • Ekinci D, Ceyhun SB, Senturk M, Characterization and anions inhibition studies of an alpha-carbonic anhydrase from the teleost fish Dicentrarchus labrax. Bioorg Med Chem 2011;19:744-8
  • Ekinci D, Senturk M, Beydemir S, An alternative purification method for human serum paraoxonase 1 and its interactions with sulfonamides. Chem Biol Drug Des 2010;76:552-8
  • Aksakal E, Ceyhun SB, Erdogan O, Ekinci D. Acute and long-term genotoxicity of deltamethrin to insulin-like growth factors and growth hormone in rainbow trout. Comp Biochem Phys Chem 2010;152:451-5
  • Dogne JM, Supuran CT, Pratico D. Adverse cardiovascular effects of the coxibs. J Med Chem 2005;48:2251-7
  • Dogne JM, Hanson J, Supuran C, Pratico D. Coxibs and cardiovascular side-effects: From light to shadow. Curr Pharm Des 2006;12:971-5
  • Kawano T, Furuıchi T. Salicylic acid as a defense-related plant hormone. Roles of oxidative and calcium signaling paths in salicylic acid biology. In: Hayat S, Ahmad A, editors. Salicylic acid. A plant hormone. Published by Springer; Dordrecht, The Netherlands: 2007. p. 277-322
  • White RF. Acetylsalicylic acid induces resistance to tobacco mosaic virus in tobacco. Virology 1979;99:410-12
  • Rhoads DM, McIntosh L. Salicylic acid regulation of respiration in higher plants: alternative oxidase expression. Plant Cell 1992;4:1131-9
  • Antoniw JF, White RF. The effects of aspirin and polyacrylic acid on soluble leaf proteins and resistance to virus infection in five cultivars of tobacco. Phytopath Z 1980;98:331-41
  • Alvarez ME. Salicylic acid in the machinery of hypersensitive cell death and disease resistance. Plant Mol Biol 2000;44:429-42
  • Kawano T, Muto S. Mechanism of peroxidase action for salicylic acid induced generation of active oxygen species and an increase in cytosolic calcium in tobacco cell suspension culture. J Exp Bot 2000;51:685-93
  • Shakirova FM. Nespetsificheskaya ustoichivost' rastenii k stressovym faktoram i ee regulyatsiya (Unspecific Plant Resistance to Stress Factors and Its Regulation). Ufa; Gilem: 2001. p. 52
  • Durner J, Klessig DF. Inhibition of ascorbate peroxidase by salicylic acid and 2,6-Dichloroisonicotinic acid, two inducers of plant defense. Proc Natl Acad Sci USA 1995;92:11312-16
  • Guan L, Scandalios JG. Developmentally related responses of maize catalase gene to salicylic acid. Proc Natl Acad Sci USA 1995;92:5930-54
  • Chen Z, Iyer S, Caplan A, Differential accumulation of salicylic acid-sensitive catalase in different rice tissues. Plant Physiol 1997;114:193-201
  • Agrawal GK, Rakwal R, Jwa N-S. Cloning and Characterization of a Jasmonate Inducible Rice (Oriza sativa L.) Peroxidase Gene OsPOX against Global Signaling Molecules and Certain Inhibitors of Kinase-Signaling Cascade(s). Plant Sci 2002;162:49-58
  • Maksimov IV, Yarullina LG. Salicylic acid and local resistance to pathogens. In: Hayat S, Ahmad A, editors. Salicylic acid. A plant hormone. Published by Springer; Dordrecht, The Netherlands: 2007. p. 323-34
  • Hippeli S, Heiser I, Elstner EF. Activated oxygen and free oxygen radicals in pathology: New insights and analogies between animals and plants. Plant Physiol Biochem 1999;37:167-78
  • Custers JHHV, Harrison SJ, Sela-Buurlage MB, Isolation and characterisation of a class of carbohydrate oxidases from higher plants, with a role in active defence. Plant J 2004;39:147-60
  • Dumas B, Freyssinet G, Pallet RE. Tissue-specific expression of germin-like oxalate oxidase development and fungal infection of barley seedlings. Plant Physiol 1995;107:1091-6
  • Chaturvedi R, Shah J. Salicylic acid in plant disease resistance. In: Hayat S, Ahmad A, editors. Salicylic acid. A plant hormone. Published by Springer; Dordrecht, The Netherlands: 2007. p. 335-70
  • Malamy J, Klessig DF. Salicylic acid and plant disease resistance. Plant J 1992;2:643-54
  • Ryals JA, Neuenschwander UH, Willits MG, Systemic acquired resistance. Plant Cell 1996;8:1809-19
  • Shah J, Klessig DF. Salicylic acid: signal perception and transduction. In: Hooykaas PPJ, Hall MA, Libbenga KR, editors. Biochemistry and Molecular Biology of Plant Hormones. Elsevier; Amsterdam, Netherlands: 1999. p. 513-41
  • Wasternack C, Atzorn R, Jarosch B, Kogel KH. Induction of a thionin, the jasmonate-induced 6 kDa protein of barley by 2,6,-dichloroisonicotinic acid. J Phytopathol 1994;140:280-4
  • Kogel K-H, Beckhove U, Dreschers J, Acquired resistance in barley. Plant Physiol 1994;106:1269-77
  • Gorlach J, Volrath S, Knauf-Beiter G, Benzothiadiazole, a novel class of inducers of systemic acquired resistance, activates gene expression and disease resistance in wheat. Plant Cell 1996;8:629-43
  • Morris SW, Vernooij B, Titatarn S, Induced resistance responses in maize. Mol Plant Microbe Interact 1998;11:643-58
  • Pasquer F, Isidore E, Zarn J, Keller B. Specific patterns of changes in wheat gene expression after treatment with three antifungal compounds. Plant Mol Biol 2005;57:693-707
  • Makandar R, Essig JS, Schapaugh MA, Genetically engineered resistance to Fusarium head blight in wheat by expression of Arabidopsis NPR1. Mol Plant Microbe Interact 2006;19:123-9
  • Singh DP, Moore CA, Gilliland A, Carr JP. Activation of multiple antiviral defense mechanisms by salicylic acid. Mol Plant Pathol 2004;5:57-63
  • Dempsey DA, Shah J, Klessig DF. Salicylic acid and disease resistance in plants. Crit Rev Plant Sci 1999;18:547-75
  • Kohler A, Schwindling S, Conrath U. Benzothiadiazole-induced priming for potentiated responses to pathogen infection, wounding, and infiltration of water into leaves require the NPR1/NIM1 gene in Arabidopsis. Plant Physiol 2002;128:1046-56
  • Malamy J, Carr JP, Klessig DF, Raskin I. Salicylic acid: a likely endogenous signal in the resistance response of tobacco to viral infection. Science 1990;250:1002-4
  • Metraux JP, Signer H, Ryals J, Increase in salicylic acid at the onset of systemic acquired resistance in cucumber. Science 1990;250:1004-6
  • Rasmussen JB, Hammerschmidt R, Zook MN. Systemic induction of salicylic acid accumulation in cucumber after inoculation with Pseudomonas syringae pv syringae. Plant Physiol 1991;97:1342-7
  • Smith JA, Hammerschmidt R, Fulbright DW. Rapid induction of systemic resistance in cucumber by Pseudomonas syringae pv. syringae. Physiol Mol Plant Pathol 1991;38:223-35
  • Chowdhury MA, Abdellatif KRA, Dong Y, Synthesis and biological evaluation of salicylic acid and N-acetyl-2-carboxybenzenesulfonamide regioisomers possessing a N-difluoromethyl-1,2-dihydropyrid-2-one pharmacophore: dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity. Bioorg Med Chem Lett 2009;19:6855-61
  • Appel B, Rotzoll S, Reinke H, Domino Michael/Retro-Michael/Mukaiyama-aldol reactions of 1,3-bis-silyl enol ethers with 3-acyl- and 3-formylbenzopyrylium triflates-synthesis of functionalised 2,4'-dihydroxybenzophenones. Eur Org Chem 2006;2006:3638-44
  • Holtz E, Albrechta U, Langer P. One-pot reactions of 2,4- (dioxobutylidene) phosphoranes. Efficient synthesis of 4-(2-hydroxybenzoyl)salicylic acid derivatives and buta-1,3-diene-1,4-dicarboxylates. Tetrahedron 2007;63:3293-301
  • Hayat S, Ali A, Ahmad A. Salicylic acid: biosynthesis, metabolism and physiological role in plants. In: Hayat S, Ahmad A, editors. Salicylic acid. A plant hormone. Published by Springer; Dordrecht, The Netherlands: 2007. p. 1-14
  • Yalpani N, Schulz M, Davies MP, Balke NE. Partial purification of an inducible uridine-5'-diphosphate glucose: salicylic acid glucosyltransferase from oat roots. Plant Physiol 1992;100:457-63
  • Alibert G, Ranjeva R. Recharches sur les enzymes catalysant la biosynthese des acides phenoliques chez Quarcus pedunculata (Ehrn): I – Formation des series cinnamique et benzoique. FEBS Lett 1971;19:11-14
  • Alibert G, Ranjeva R. Recharches sur les enzymes catalysant la biosyntheses des acid phenoliques chez Quarcus pedunculata (Ehrn): II- Localization intercellulaire de la phenylalanin mmonique-lyase, de la cinnamate 4-hydroxylase, et de la “benzoate synthase”. Biochem Biophys Acta 1972;279:282-9
  • Russell DW, Conn EE. The cinnamic acid 4-hydroxylase of pea seedlings. Arch Biochem Biophys 1967;122:256-8
  • Gabriace B, Werck-Reichhart D, Teutsch H, Durst F. Purification and immunocharacterization of a plant cytochrome P450: the cinnamic acid 4-hydroxylase. Arch Biochem Biophys 1991;288:302-9
  • Gestetner B, Conn EE. The 2-hydroxylation of transcimannic acid by chloroplasts from Melilotus alba Desr. Arch Biochem Biophys 1974;163:617-24
  • Gasco A, Fruttero R, Lazzarato R, Donnola M. Salicylic acid derivatives. US0293781; 2008
  • Aubert L. Method of shaving using salicylic acid derivatives. US0224204; 2010
  • Hansenne I, Cornell M, Fares H, Foltis P. Salicylic acid derivative as efficacy enhancer and method. WO073745; 2004
  • Quedville S, Remaut G, Potin A. Roll-on with high salicylic acid content. US0256100;2010
  • Strodtholtz I, Schmidt I, Strahinjie I. Skincare compositions comprising salicyclic acid. US0311308; 2009
  • Lee J. Acidic antibiotic composition containing peracid and acetyl salicylic acid. WO057835; 2009
  • Dhuppad UR, Khachane VS, Bhamre NB, Sharma AD. Topical composition comprising halobetasol and salicylic acid. WO084020; 2009
  • Holzl W, Purschwitz J. Antimicrobial amino-salicylic acid derivatives. WO023573; 2011
  • Ovil Y. Salicylic salt compositions and related method of treatment of cardiac conditions. US0075930; 2010
  • Gwag B, Cho S, Cho J, Salicylic acid derivative compound and pharmaceutical composition containing them. WO119984; 2007
  • Jasra RV, Tyagi B, Mishra MK. Green catalytic process for the synthesis of acetyl salicylic acid. US7544831; 2009

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