Design, Synthesis and Characterization of 2,4-Dimethylphenyl Hydrazine based Chemosensors
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Hydrazones are a unique division of compounds found in various syntheses. They have an important role in synthetic chemistrydue to their different biological properties, such as antifungal, anticonvulsant, antibacterial, antimalarial, anti-inflammatory and anti-TB properties. This paper reports the syntheses of a series of 3 hydrazones based on the condensation of 2,4-dimethylphenyl hydrazine HCl with different aromatic carbonyl compounds. The structures of the synthesized compounds were confirmed by EIMS. These compounds can act as ideal candidates in chemosensor chemistry.
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Malele CN. Design, synthesis and photophysics of dipyrrolequinoxaline receptor loaded fluorescent conjugated polymer chemosensors. 2019. https://www.antoineonline.com/Product.aspx?productCode=0009781244072510
Shi P, Zhang J. Extraordinary diversity of chemosensory receptor gene repertoires among vertebrates. Results Probl Cell Differ. 2009;47: 57–58.
Jing W, Chang H-S, Xu ZC, et al. A colorimetric and fluorescent turn-on chemosensor for Zn+2 based on an azobenzene-containing compound. J Tetrahedron. 2009;65: 2307–6964.
Ellen R, Goldman IL, Medintz JL, et al. A hybrid quantum dot−antibody fragment fluorescence resonance energy transfer-based TNT sensor. J Am Chem Soc. 2005;127(18): 6744–51.
Marwan S, Abdussalam S,Tan T, Saleh MI, Bahruddin S. Spectroscopic studies of 1,4-bis(4-dimethylaminobenzyl)-2,3-diaza-1,3-butadieneas Colorimetric Reagent for Cu+2” . World Appl Sci J. 2011;15(4): 598–605.
Ragnarsson U. Synthetic methodology for alkyl substituted hydrazines. Chem Soc Rev. 2011;30: 205–213.
Narayanan SS, Scholz F. A comparative study of the electrocatalytic activities of some metal hexacyanoferrates for the oxidation of hydrazine. Electroanalysis. 1999; 11(7): 465–469.
Khomsan T, Rattha N, Sinchai C, et al. A chromogenic and fluorogenic rhodol-based chemosensor for hydrazine detection and its application in live cell bioimaging. Spectrochim Acta A Mol Biomol Spectrosc. 2018; 195: 136–141. https://www.researchgate.net/publication/322459741
Bhutani H, Singh S, Vir S, et al. LC and LC-MS study of stress decomposition behaviour of isoniazid and establishment of validated stability-indicating assay method. J Pharm Biomed Anal. 2007;l43: 1213–1220.
Liu J, Zhou W, You T, Li F, Wang E, Dong S. Detection of hydrazine, methylhydrazine, and isoniazid by capillary electrophoresis with a palladium-modified microdisk array electrode. Anal Chem. 1996;68: 3350–3353.
Sun T, Wetzel SJ, Johnson ME, Surlow BA, Patton J-V. Development and validation of a hydrophilic interaction liquid chromatography-tandem mass spectrometry method for the quantification of lipid-related extracellular metabolites in Saccharomyces cerevisiae. J Chromatogr B. 2012;897: 1–9. doi:10.1016/j.jchromb.2012.03.034
March J. Advanced organic chemistry: reactions, mechanisms, and structure (3rd ed.). New York: Wiley; 1985.
Rahman VM, Mukhtar S, Ansari WH, Lemiere G. Synthesis, stereochemistry and biological activity of some novel long alkyl chain substituted thiazolidin-4-ones and thiazan-4-one from 10-undecenoic acid hydrazide. Eur J Med Chem. 2005;40: 173–184.
Dimmock JR, Vashishtha SC, Stables JP. Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds. Eur J Med Chem. 2000; 35: 241–248.
Yapia R, La Mara MP, Massieu GH. Modifications of brain glutamate decarboxylase activity by pyridoxal phosphate-β-glutamyl hydrazone. Biochem. Pharmacol. 1967;16: 1211–1218.
Sava G, Perissin L, Lassiani L, Zabucchi G. Antiinflammatory action of hydrosoluble dimethyl-triazenes on the carrageen induced edema in guinea pigs. Chem Biol Interact. 1985;53: 37–43.
Xia YL, Chuan-Dong F, Zhao BX, Zhao J, Shin DS, Miaom JY. Synthesis and structure-activity relationships of novel 1-arylmethyl-3-aryl-1H- pyrazole-5-carbohydrazide hydrazone derivatives as potential agents A549 lung cancer cells. Eur J Med Chem. 2008;43: 2347–2353.
Melnyk P, Leroux V, Serghergert C, Grellier P. Design, synthesis and in vitro antimalarial activity of an acylhydrazone library. Bioorg Med Chem Lett. 2006;16: 31–35.
Ajani OO, Obafemi CA, Nwinyi OC, Akinpelu DA. Microwave assisted synthesis and antimicrobial activity of 2- quinoxalinone-3-hydrazone derivatives. Bioorg Med Chem. 2010;18: 214–221.
Zheng LW, Wu LL, Zhao BX, Dong WL, Miao YJ. Synthesis of novel substituted pyrazole-5-carbohydrazide hydrazone derivatives and discovery of a potent apoptosis inducer in A549 lung cancer cells. Bioorg Med Chem. 2009;17: 1957–1962.
Bhagavan NV. Medical biochemistry. 4th ed. Amsterdam, The Netherlands: Elsevier; 2002.
Saulnier MG, Velaprthi U, Zimmermann K. Progress in heterocyclic synthesis. In: Gordon W. Gribble, J. Joule, ed. Five-membered ring system: with N and S (SE) atoms. Vol. 16. Amsterdam, The Netherlands: Elseiver; 2005.
Short EI. Studies on the inactivation of isonicotinyl acid hydrazide in normal subjects and tuberculous patients. Tubercle. 1962;43: 33–42.
Holdiness MR. A review of blood dyecrasias induced by the antituberculosis drugs. Tubercle. 1987;68: 301–309.
Faroumadi A, Kiano Z, Soltani F. Antituberculosis agents VIII: synthesis and in vitro antimycobacterial activity of alkyl a-[5-(5-nitro-2-thienyl)-1,3,4- thiadiazole-2-ylthio] acetates. Farmaco. 2003;58: 1073–1076.
Wu AM, Senter PD. Arming antibodies: prospects and challenges for immunoconjugates. Nat Biotechnol. 2005;23(9): 1137–46.
Yuee Y, Yan H, Guopo Z, Xingming K. A novel azathia-crown ether dye chromogenic chemosensor for the selective detection of mercury(II) ion. Dyes Pigm, 2008;79(2): 210–215.
Chen C. Fluorescent, sequence-selective peptide detection by synthetic small molecules. Science. 1998;279(5352): 851–853.
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