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Vol. 12 No. 2 (2021)
Vol 12, Núm.2 (2021): Julio-Diciembre

Artículos de investigación / Research papers

Synthesis Of A Schiff Base Derivade From Dopamine And Cinamaldehyde

https://doi.org/10.19053/01217488.v12.n2.2021.8500

Published 2021-09-07

  • Eliana Maritza Tulcán Mejía
    • ,
  • Johan Fabian Galindo Cruz
    • ,
  • Carmen Rosa Perez Figueredo

Eliana Maritza Tulcán Mejía
Universidad Pedagógica y Tecnológica de Colombia

Johan Fabian Galindo Cruz
Universidad Nacional de Colombia

Carmen Rosa Perez Figueredo
Universidad Pedagógica y Tecnológica de Colombia

Abstract

In this research paper, evidences of the synthesis of a Schiff's base from dopamine and cinnamaldehyde, synthesized via wet condensation are reported. This compound was analyzed by infrared and visible ultraviolet spectroscopy; the experimental results were compared with those obtained by the Density Functional Theory (DFT) method. The analyzes allowed the research to confirm the obtained specie: 4-(2-{[(1E,2E)-3-phenylprop-2-en-1-ylidene]amino}ethyl)benzene-1,2-diol.

Keywords

cinamaldehyde, dopamine, Schiff base

PDF (Español)

References

  1. C. Godoy-Alcántar, A. K. Yatsimirsky, and J. M. Lehn, "Structure-stability correlations for imine formation in aqueous solution," Journal of Physical Organic Chemistry, vol. 18, pp. 979-985, 2005. DOI: https://doi.org/10.1002/poc.941
  2. Y. Hijji, R. Rajan, H. B. Yahia, S. Mansour, A. Zarrouk, and I. Warad, "One‐pot microwave‐assisted synthesis of water‐soluble pyran‐2,4,5‐triol glucose amine schiff base derivative: Xrd/hsa interactions, crystal structure, spectral, thermal and a DFT/TD‐DFT," Crystals, vol. 11, pp. 1-14, 2021. DOI: https://doi.org/10.3390/cryst11020117
  3. L. Zhao, S. Liu, Y. Cai, and J. Chen, "A New Synthesis of the Schiff Base Derived from 2, 3, 4- Trihydroxybenzaldehyde and 4-Aminobenzoic Acid via Airflow Grinding Technology," in IOP Conference Series: Earth and Environmental Science, 2020. DOI: https://doi.org/10.1088/1755-1315/565/1/012046
  4. D. S. Chauhan, M. A. J. Mazumder, M. A. Quraishi, K. R. Ansari, and R. K. Suleiman, "Microwave-assisted synthesis of a new Piperonal-Chitosan Schiff base as a bio-inspired corrosion inhibitor for oil-well acidizing," International Journal of Biological Macromolecules, vol. 158, pp. 231-243, 2020. DOI: https://doi.org/10.1016/j.ijbiomac.2020.04.195
  5. M. T. Asadi, Susan; Mohammadi, Khosro, "Synthesis, characterization, and thermodynamics of some new unsymmetrical Schiff bases of salicylaldehyde with 3,4-diaminopyridine and their cobalt(III) complexes," Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 122, pp. 676-681, 2014. DOI: https://doi.org/10.1016/j.saa.2013.09.098
  6. S. H. Rahaman, R. Ghosh, and B. K. Ghosh, "Heteromeric hydrogen bonded 2D supramolecule using heptacoordinated end-on azido bridged centrosymmetric dinuclear cadmium(II)Schiff base building block," Inorganic Chemistry Communications, vol. 9, pp. 1011-1014, 2006. DOI: https://doi.org/10.1016/j.inoche.2006.04.020
  7. A. B. K. Subhash B Junne, Sainath B Zangade, Saheb L Shinde, Yeshwant B Vibhute, "Synthesis and antibacterial activity of some new schiff bases and 2-Azetidinones containing iodohyydroxy biphenyl moiety," BANGLADESH JOURNAL OF PHARMACOLOGY, vol. 10, pp. 555-561, 2015.
  8. B. Shipra and C. Sumitra, "Synthesis and Investigation of Antibacterial activity of Some Schiff bases," Journal of Chemical, Biological and Physical Sciences (JCBPS), vol. 2, pp. 1176-1183, May-Jul 2012.
  9. K.-R. Aggarwal-Nisha, Dureja-Prem, Rawat-Diwan S., "Schiff Bases as Potential Fungicides and Nitrification Inhibitors," Journal of Agricultural and Food Chemistry, vol. 57, pp. 8520-8525, 2009. DOI: https://doi.org/10.1021/jf902035w
  10. T. Aboul-Fadl, A. A. Radwan, M. I. Attia, A. Al-Dhfyan, and H. A. Abdel-Aziz, "Schiff bases of indoline-2,3-dione (isatin) with potential antiproliferative activity," Chemistry Central Journal, vol. 6, p. 49, 2012. DOI: https://doi.org/10.1186/1752-153X-6-49
  11. S. Adsule, V. Barve, D. Chen, F. Ahmed, Q. P. Dou, S. Padhye, et al., "Novel Schiff Base Copper Complexes of Quinoline-2 Carboxaldehyde as Proteasome Inhibitors in Human Prostate Cancer Cells," Journal of Medicinal Chemistry, vol. 49, pp. 7242-7246, 2006. DOI: https://doi.org/10.1021/jm060712l
  12. J. Joseph and K. Nagashri, "Novel Copper-Based Therapeutic Agent for Anti-Inflammatory: Synthesis, Characterization, and Biochemical Activities of Copper(II) Complexes of Hydroxyflavone Schiff Bases," Applied Biochemistry and Biotechnology, vol. 167, pp. 1446-58, 2012. DOI: https://doi.org/10.1007/s12010-011-9529-z
  13. U. Markandan, A. Ekamparam, and R. Rangappan., "Synthesis and spectral investigations of binuclear Schiff base metal complexes derived from 1, 5-diaminonaphthalene," Journal of Chemical, Biological and Physical Sciences (JCBPS), vol. 2, pp. 677-682, 2012.
  14. G. D. Yadav and M. S. Krishnan, "An Ecofriendly Catalytic Route for the Preparation of Perfumery Grade Methyl Anthranilate from Anthranilic Acid and Methanol," Organic Process Research & Development, vol. 2, pp. 86-95, 1998. DOI: https://doi.org/10.1021/op970047d
  15. S. M. A. Hosseini and A. Azimi, "The inhibition effect of the new Schiff base, namely 2,2′-[bis-N(4-choloro benzaldimin)]-1,1′-dithio against mild steel corrosion," Materials and Corrosion, vol. 59, pp. 41-45, 2008. DOI: https://doi.org/10.1002/maco.200704101
  16. F. K. Abbas Afkhami*, and Hamid Khanmohammadi, "Spectrophotometric Determination of Complex Formation Constants Between a New Schiff Base and Some Transition Metals by Rank Annihilation Factor Analysis," J. Chem. Eng., vol. 54, pp. 866-870, 2009. DOI: https://doi.org/10.1021/je800663v
  17. R. Yan, P. G. Liu, Z. M. Zhang, X. Y. Fang, X. W. Zhang, J. L. Deng, et al., "Synthesis, biological evaluation and molecular modeling studies of Schiff bases derived from 4-methylsalicylic acid as potential immunosuppressive agents," Medicinal Chemistry Research, vol. 22, pp. 5707-5716, 2013. DOI: https://doi.org/10.1007/s00044-013-0561-0
  18. R. R. L. Beltrán, "Síntesis, caracterización y actividad antibacteriana de complejos metálicos con bases de Schiff que contienen cefradina," Departamento de Química, UNIVERSIDAD DE ORIENTE, Cumaná - Venezuela, 2009.
  19. K. Gangarapu, Development of Isatin as CNS Agents: Anticonvulsant activity. Germany: Anchor Academic Publishing, 2015.
  20. M. Sirajuddin, N. Uddin, S. Ali, and M. N. Tahir, "Potential bioactive Schiff base compounds: Synthesis, characterization, X-ray structures, biological screenings and interaction with Salmon sperm DNA," Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 116, pp. 111-121, 2013. DOI: https://doi.org/10.1016/j.saa.2013.06.096
  21. N. A. Illán-Cabeza, F. Hueso-Ureña, M. N. Moreno-Carretero, J. M. Martínez-Martos, and M. J. Ramírez-Expósito, "Synthesis, characterization and antiproliferative activity of metal complexes with the Schiff base derived from the condensation 1:2 of 2,6-diformyl-4-methylphenol and 5,6-diamino-1,3-dimethyluracil," Journal of Inorganic Biochemistry, vol. 102, pp. 647-655, 2008. DOI: https://doi.org/10.1016/j.jinorgbio.2007.10.008
  22. K. C. Gupta and A. K. Sutar, "Catalytic activities of Schiff base transition metal complexes," Coordination
  23. Chemistry Reviews, vol. 252, pp. 1420-1450, 2008. DOI: https://doi.org/10.1016/j.ccr.2007.09.005
  24. M. Lenz, N. Borlinghaus, L. Weinmann, and B. M. Nestl, "Recent advances in imine reductase-catalyzed reactions," World Journal of Microbiology and Biotechnology, vol. 33, 2017. DOI: https://doi.org/10.1007/s11274-017-2365-8
  25. S. Yu, J. Feng, T. Cai, and S. Liu, "Schiff Base Bridged Phenolic Diphenylamines for Highly Efficient and Superior Thermostable Lubricant Antioxidants," Industrial & Engineering Chemistry Research, vol. 56, 2017. DOI: https://doi.org/10.1021/acs.iecr.7b00313
  26. M. D. Rudrapal, Biplab, "Chemistry and Biological Importance of Heterocyclic Schiff's Bases," International Research Journal of Pure and Applied Chemistry, vol. 3, pp. 232-249, Jul-Sep2013 2013. DOI: https://doi.org/10.9734/IRJPAC/2013/3996
  27. A. A. Al-Amiery, "Synthesis and antioxidant, antimicrobial evaluation, DFT studies of novel metal complexes derivate from Schiff base," Res Chem Intermed, vol. 38, pp. 745–759, 2012. DOI: https://doi.org/10.1007/s11164-011-0414-8
  28. A. Kawashima, S. Shu, R. Takeda, A. Kawamura, T. Sato, H. Moriwaki, et al., "Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base," Amino Acids, vol. 48, pp. 973-986, 2016. DOI: https://doi.org/10.1007/s00726-015-2138-3
  29. B. Bouzerafa, A. Ourari, D. Aggoun, R. Ruiz-Rosas, Y. Ouennoughi, and E. Morallon, "Novel nickel(II) and manganese(III) complexes with bidentate Schiff-base ligand: synthesis, spectral, thermogravimetry, electrochemical and electrocatalytical properties," Research on Chemical Intermediates, vol. 42, pp. 4839-4858, 2016. DOI: https://doi.org/10.1007/s11164-015-2325-6
  30. R. Antony, S. T. D. Manickam, and S. Balakumar, "Cu(II), Co(II) and Ni(II) Complexes Installed on Functionalized Silica Surface for Hydrogen Peroxide Assisted Cyclohexane Oxidation," Journal of Inorganic and Organometallic Polymers and Materials, vol. 27, pp. 418-426, 2017. DOI: https://doi.org/10.1007/s10904-016-0482-8
  31. M. Nikoorazm, A. Ghorbani-Choghamarani, and N. Noori, "Synthesis, characterization, and catalytic application of Cr and Mn Schiff base complexes immobilized on modified nanoporous MCM-41," Research on Chemical Intermediates, vol. 42, pp. 4621-4640, 2016. DOI: https://doi.org/10.1007/s11164-015-2304-y
  32. A. G. Mahmoud, K. T. Mahmudov, M. F. C. Guedes Da Silva, and A. J. L. Pombeiro, "Reaction of sodium 2-(2-(2,4-dioxopentan-3-ylidene)hydrazinyl) benzenesulfonate with ethylenediamine on Cu(ii) and Ni(ii) centres: Efficient Cu(ii) homogeneous catalysts for cyanosilylation of aldehydes," RSC Advances, vol. 6, pp. 54263-54269, 2016. DOI: https://doi.org/10.1039/C6RA12274D
  33. S. Chumillas, M. C. Figueiredo, V. Climent, and J. M. Feliu, "Study of dopamine reactivity on platinum single crystal electrode surfaces," Electrochimica Acta, vol. 109, pp. 577-586, 2013. DOI: https://doi.org/10.1016/j.electacta.2013.07.107
  34. O. Kocyigit, "A novel Schiff base bearing dopamine groups with tripodal structure. Synthesis and its salen/salophen-bridged Fe/Cr(III) capped complexes," Journal of Molecular Structure, vol. 1034, pp. 69-74, 2013. DOI: https://doi.org/10.1016/j.molstruc.2012.09.008
  35. M. H. Amir Adabiardakani, Hadi Kargar, "Cinnamaldehyde Schiff Base Derivatives: A Short Review," World Applied Programming, vol. 2, pp. 472-476, 2012.
  36. S. Shreaz, R. A. Shiekh, V. Raja, W. A. Wani, and J. M. Behbehani, "Impaired ergosterol biosynthesis mediated fungicidal activity of Co(II) complex with ligand derived from cinnamaldehyde," Chemico-Biological Interactions, vol. 247, pp. 64-74, 2016. DOI: https://doi.org/10.1016/j.cbi.2016.01.015
  37. R. Quevedo, C. Díaz-Oviedo, and Y. Quevedo-Acosta, "Role of hydroxyl groups on the aromatic ring in the reactivity and selectivity of the reaction of β -phenylethylamines with non-enolizable aldehydes," Research on Chemical Intermediates, vol. 41, pp. 9835-9843, 2015. DOI: https://doi.org/10.1007/s11164-015-1987-4
  38. S. Chigurupati, M. Selvaraj, V. Mani, J. I. Mohammad, K. K. Selvarajan, S. S. Akhtar, et al., "Synthesis of azomethines derived from cinnamaldehyde and vanillin: in vitro aetylcholinesterase inhibitory, antioxidant and insilico molecular docking studies," Medicinal Chemistry Research, vol. 27, pp. 807-816, 2018. DOI: https://doi.org/10.1007/s00044-017-2104-6
  39. I. Khan, M. Shahid, and D. Kabir ud, "Kinetics of the complex formation of chromium(III) with L-hydroxyproline. Mechanistic difference between hexaaquachromium(III) ion and pentaaquahydroxochromium(III) ions in their complexation," Transition Metal Chemistry, vol. 12, pp. 393-397, 1987. DOI: https://doi.org/10.1007/BF01171644
  40. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, et al., "Gaussian 16 Rev. C.01," ed. Wallingford, CT, 2016.
  41. H. P. Ebrahimi, J. S. Hadi, Z. A. Abdulnabi, and Z. Bolandnazar, "Spectroscopic, thermal analysis and DFT computational studies of salen-type Schiff base complexes," Spectrochim Acta A Mol Biomol Spectrosc, vol. 117, pp. 485-92, Jan 3 2014. DOI: https://doi.org/10.1016/j.saa.2013.08.044
  42. D. A. Case, H. M. Aktulga, K. Belfon, I. Y. Ben-Shalom, S. R. Brozell, D. S. Cerutti, et al., "Amber 2021," ed. San Francisco: University of California, 2021.
  43. Y. Ma, B. Fan, T. Zhou, H. Hao, B. Yang, and H. Sun, "Molecular assembly between weak crosslinking cyclodextrin polymer and Trans-cinnamaldehyde for corrosion inhibition towards mild steel in 3.5% NaCl solution: Experimental and theoretical studies," Polymers, vol. 11, 2019. DOI: https://doi.org/10.3390/polym11040635
  44. M. G. Prakash, R. Mahalakshmy, K. R. Krishnamurthy, and B. Viswanathan, "Selective hydrogenation of cinnamaldehyde on nickel nanoparticles supported on titania: Role of catalyst preparation methods," Catalysis Science and Technology, vol. 5, pp. 3313-3321, 2015. DOI: https://doi.org/10.1039/C4CY01379D
  45. A. B. K. Subhash B. Junne, Sainath B. Zangade, Saheb L. Shinde, Yeshwant B. Vibhute, "Synthesis and antibacterial activity of some new schiff bases and 2-Azetidinones containing iodohyydroxy biphenyl moiety," International Multidisciplinary Research Journal, vol. 2, pp. 44-47, 2012.
  46. A. Lagutschenkov, J. Langer, G. Berden, J. Oomens, and O. Dopfer, "Infrared spectra of protonated neurotransmitters: dopamine," Physical Chemistry Chemical Physics, vol. 13, pp. 2815-2823, 2011. DOI: https://doi.org/10.1039/C0CP02133D
  47. A. L. Nicely, D. J. Miller, and J. M. Lisy, "Charge and Temperature Dependence of Biomolecule Conformations: K+Tryptamine(H2O)n=0−1Arm=0−1 Cluster Ions," Journal of the American Chemical Society, vol. 131, pp. 6314-6315, 2009. DOI: https://doi.org/10.1021/ja8094526
  48. J. Mohan, Organic Spectroscopy: Principles and Applications, Second ed. India: Alpha Science International Ltd., 2004.
  49. O. Jha, T. K. Yadav, and R. A. Yadav, "Structural and vibrational study of a neurotransmitter molecule: Dopamine [4-(2-aminoethyl) benzene-1,2-diol]," Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 189, pp. 473-484, 2018. DOI: https://doi.org/10.1016/j.saa.2017.07.067
  50. R. T. Conley, Espectroscopia Infrarroja, Primera Edición ed. Madrid: Editorial lhambra S. A., 1979.
  51. C. Hernandez T and R. G. E. Morales, "Bridge effect in charge-transfer photoconduction channels. 1. Aromatic carbonyl compounds," The Journal of Physical Chemistry, vol. 97, pp. 11649-11651, 1993. DOI: https://doi.org/10.1021/j100147a016
  52. W. O. Foye, Principles of Medicial Chemistry, Lea & Febiger ed. United States of America, 1989.
  53. P. Kovacic, R. S. Pozos, R. Somanathan, N. Shangari, and P. J. O'Brien, "Mechanism of mitochondrial uncouplers, inhibitors, and toxins: Focus on electron transfer, free radicals, and structure-activity relationships," Current Medicinal Chemistry, vol. 12, pp. 2601-2623, 2005. DOI: https://doi.org/10.2174/092986705774370646

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