Main Article Content
Abstract
Aminoalkylation of vanillin (4-hydroxy-3-methoxybenzaldehyde) was achieved by reactions of vanillin with formaldehyde and suitable amine in acetonitrile. The products aminoalkyalted vanillin compounds 1-5 were purified by column and thin layer chromatography and identified by spectroscopic methods viz. UV, IR, NMR and mass spectrometry.
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References
- D.A. Mutlu and C. Vnsal, Synthesis of Some Novel Mannich Bases Derived from Allomaltol and Evaluation of their Anticonvulsant Activities, Hacettepe Univ. J. Faculty Pharm., 27, 1 (2007).
- R. Ozan, O. Zuhal, C. Unsal, G. Butent and A.B. Abdullah, Synthesis of and Pharmacological Studies on the Antidepressant and Anticonvul-sant Activities of Some 1,3,5-Trisubstituted Pyrazolines, Arzneimittel-forschung, 55, 431 (2005); https://doi.org/10.1055/s-0031-1296884.
- M.N. Aboul-Enein, A.A. El-Azzouny, N.A. Abdallah, S.M. Moharam, W. Werner, A. Eid and A.A. Makhluf, Synthesis of Some 6-(Alkylamino)-methyl hexahydro-5-aryl- and Aralkyl-4,7-methanoindan-5-ols and Certain of their Propionate Esters as Analgesics, J. Islamic Acad. Sci., 6, 99 (1993).
- R.M. Moriarty, S. Grubjesic, B.C. Surve, S.N. Chandersekera, O. Prakash and R. Naithani, Synthesis of Abyssinone II and Related Compounds as Potential Chemopreventive Agents, Eur. J. Med. Chem., 41, 263 (2006); https://doi.org/10.1016/j.ejmech.2005.09.008.
- H.I. Gul, J. Vepsalainen, M. Gul, E. Erciyas and O. Hanninen, Cytotoxic Activities of Mono and Bis Mannich Bases Derived from Acetophenone against Renca and Jurkat Cells, Pharm. Acta Helv., 74, 393 (2000); https://doi.org/10.1016/S0031-6865(00)00022-4.
- E. Mete, H. Gul and C. Kazaz, Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides as Possible Potent Cytotoxic Agents, Molecules, 12, 2579 (2007); https://doi.org/10.3390/12122579.
- J.R. Dimmock, A. Jha, P. Kumar, G.A. Zello, J.W. Quail, E.O. Oloo, J.J. Oucharek, M.K. Pasha, D. Seitz, R.K. Sharma, T.M. Allen, C.L. Santos, E.K. Manavathu, E. De Clercq, J. Balzarini and J.P. Stables, Cytotoxic 1,4-bis(2-Oxo-1-cycloalkylmethylene)benzenes and Related Compounds, Eur. J. Med. Chem., 37, 35 (2002); https://doi.org/10.1016/S0223-5234(01)01294-6.
- S.J. Kesten, J. Johnson and L.M. Werbel, Antimalarial Drugs: 61. Synthesis and Antimalarial Effects of 4-[(7-Chloro-4-quinolinyl)amino] -2-[(diethylamino)methyl]-6-alkylphenols and their Nw-oxides, J. Med. Chem., 30, 906 (1987); https://doi.org/10.1021/jm00388a027.
- T. Lorand, B. Kocsis, P. Sohar, G. Nagy, P. Jozsef, G. Kispal, R. Laszlo and L. Prókai, Synthesis and Antibacterial Activity of Fused Mannich Ketones, Eur. J. Med. Chem., 37, 803 (2002); https://doi.org/10.1016/S0223-5234(02)01404-6.
- A. El-Masry, H. Fahmy and S.A. Abdelwahed, Synthesis and Antimi-crobial Activity of Some New Benzimidazole Derivatives, Molecules, 5, 1429 (2000); https://doi.org/10.3390/51201429.
- J.R. Dimmock, S.C. Vashishtha, J.W. Quail, U. Pugazhenthi, Z. Zimpel, A.M. Sudom, T.M. Allen, G.Y. Kao, J. Balzarini and E. De Clercq, 4-(b-Arylvinyl)-3-(b-arylvinylketo)-1-ethyl-4-piperidinols and Related Compounds: A Novel Class of Cytotoxic and Anticancer Agents, J. Med. Chem., 41, 4012 (1998); https://doi.org/10.1021/jm9801455.
- S. Bala, N. Sharma, A. Kajal, S. Kamboj and V. Saini, Mannich Bases: An Important Pharmacophore in Present Scenario, Int. J. Med. Chem., http://dx.doi.org/10.1155/2014/191072.
- A. Gómez-Rivera, H. Aguilar-Mariscal, N. Romero-Ceronio, L.F. Roa-de la Fuente and C.E.Lobato-García, Bioorg. Med. Chem. Lett., 23, 5519 (2003); https://doi.org/10.1016/j.bmcl.2013.08.061.
- F. Herencia, M.L. Ferrándiz, A. Ubeda, J.N. Domínguez, J.E. Charris, G.M. Lobo and M.J. Alcaraz, Synthesis and Anti-Inflammatory Activity of Chalcone Derivatives, Bioorg. Med. Chem. Lett., 8, 1169 (1998); https://doi.org/10.1016/S0960-894X(98)00179-6.
- H.-H. Ko, L.-T. Tsao, K.-L. Yu, C.-T. Liu, J.-P. Wang and C.-N. Lin, Structure-Activity Relationship Studies on Chalcone Derivatives: The Potent Inhibition of Chemical Mediators Release, Bioorg. Med. Chem., 11, 105 (2003); https://doi.org/10.1016/S0968-0896(02)00312-7.
- Y.-M. Lin, Y. Zhou, M.T. Flavin, L.-M. Zhou, W. Nie and F.-C. Chen, Chalcones and Flavonoids as Anti-Tuberculosis Agents, Bioorg. Med. Chem., 10, 2795 (2002); https://doi.org/10.1016/S0968-0896(02)00094-9.
- S.N. Lopez, M.V. Castelli, S.A. Zacchino, J.N. Domínguez, G. Lobo, J. Charris-Charris, J.C.G. Cortés, J.C. Ribas, C. Devia, A.M. Rodríguez and R.D. Enriz, in vitro Antifungal Evaluation and Structure-Activity Relationships of a New Series of Chalcone Derivatives and Synthetic Analogues with Inhibitory Properties against Polymers of Fungal Cell Wall, Bioorg. Med. Chem., 9, 1999 (2001); https://doi.org/10.1016/S0968-0896(01)00116-X.
- R. Li, G.L. Kenyon, F.E. Cohen, X. Chen, B. Gong, J.N. Dominguez, E. Davidson, G. Kurzban, R.E. Miller, E.O. Nuzum, P.J. Rosenthal and J.H. McKerrow, in vitro Antimalarial Activity of Chalcones and Their Derivatives, J. Med. Chem., 38, 5031 (1995); https://doi.org/10.1021/jm00026a010.
- V.S. Parmar, N.K. Sharma, M. Husain, A.C. Watterson, J. Kumar, L.A. Samuelson, A.L. Cholli, A.K. Prasad, A. Kumar, S. Malhotra, N. Kumar, A. Jha, A. Singh, I. Singh, Himanshu, A. Vats, N.A. Shakil, S. Trikha, S. Mukherjee, S.K. Sharma, S.K. Singh, A. Kumar, H.N. Jha, C.E. Olsen, C.P. Stove, M.E. Bracke and M.M. Mareel, Synthesis, Characterization and in vitro Anti-Invasive Activity Screening of Polyphenolic and Heterocyclic Compounds, Bioorg. Med. Chem., 11, 913 (2003); https://doi.org/10.1016/S0968-0896(02)00539-4.
- L.S. Pedroso, G.M. Fávero, L.E.A. De Camargo, R.M. Mainardes and N.M. Khalil, Effect of the o-Methyl Catechols Apocynin, Curcumin and Vanillin on the Cytotoxicity Activity of Tamoxifen, J. Enzyme Inhib. Med. Chem., 28, 734 (2013); https://doi.org/10.3109/14756366.2012.680064.
- J. Zhang, L. Zhao, C. Zhu, Z. Wu, G. Zhang, X. Gan, D. Liu, J. Pan, D. Hu and B. Song, Facile Synthesis of Novel Vanillin Derivatives Incorp-orating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents, J. Agric. Food Chem., 65, 4582 (2017); https://doi.org/10.1021/acs.jafc.7b01035.
- H. Korthou and R. Verpoorte, ed.: R.G. Berger, Vanilla, In: Flavours and Fragrances, Springer-Verlag, Berlin, vol. 1, pp. 203-217 (2007).
References
D.A. Mutlu and C. Vnsal, Synthesis of Some Novel Mannich Bases Derived from Allomaltol and Evaluation of their Anticonvulsant Activities, Hacettepe Univ. J. Faculty Pharm., 27, 1 (2007).
R. Ozan, O. Zuhal, C. Unsal, G. Butent and A.B. Abdullah, Synthesis of and Pharmacological Studies on the Antidepressant and Anticonvul-sant Activities of Some 1,3,5-Trisubstituted Pyrazolines, Arzneimittel-forschung, 55, 431 (2005); https://doi.org/10.1055/s-0031-1296884.
M.N. Aboul-Enein, A.A. El-Azzouny, N.A. Abdallah, S.M. Moharam, W. Werner, A. Eid and A.A. Makhluf, Synthesis of Some 6-(Alkylamino)-methyl hexahydro-5-aryl- and Aralkyl-4,7-methanoindan-5-ols and Certain of their Propionate Esters as Analgesics, J. Islamic Acad. Sci., 6, 99 (1993).
R.M. Moriarty, S. Grubjesic, B.C. Surve, S.N. Chandersekera, O. Prakash and R. Naithani, Synthesis of Abyssinone II and Related Compounds as Potential Chemopreventive Agents, Eur. J. Med. Chem., 41, 263 (2006); https://doi.org/10.1016/j.ejmech.2005.09.008.
H.I. Gul, J. Vepsalainen, M. Gul, E. Erciyas and O. Hanninen, Cytotoxic Activities of Mono and Bis Mannich Bases Derived from Acetophenone against Renca and Jurkat Cells, Pharm. Acta Helv., 74, 393 (2000); https://doi.org/10.1016/S0031-6865(00)00022-4.
E. Mete, H. Gul and C. Kazaz, Synthesis of 1-Aryl-3-phenethylamino-1-propanone Hydrochlorides as Possible Potent Cytotoxic Agents, Molecules, 12, 2579 (2007); https://doi.org/10.3390/12122579.
J.R. Dimmock, A. Jha, P. Kumar, G.A. Zello, J.W. Quail, E.O. Oloo, J.J. Oucharek, M.K. Pasha, D. Seitz, R.K. Sharma, T.M. Allen, C.L. Santos, E.K. Manavathu, E. De Clercq, J. Balzarini and J.P. Stables, Cytotoxic 1,4-bis(2-Oxo-1-cycloalkylmethylene)benzenes and Related Compounds, Eur. J. Med. Chem., 37, 35 (2002); https://doi.org/10.1016/S0223-5234(01)01294-6.
S.J. Kesten, J. Johnson and L.M. Werbel, Antimalarial Drugs: 61. Synthesis and Antimalarial Effects of 4-[(7-Chloro-4-quinolinyl)amino] -2-[(diethylamino)methyl]-6-alkylphenols and their Nw-oxides, J. Med. Chem., 30, 906 (1987); https://doi.org/10.1021/jm00388a027.
T. Lorand, B. Kocsis, P. Sohar, G. Nagy, P. Jozsef, G. Kispal, R. Laszlo and L. Prókai, Synthesis and Antibacterial Activity of Fused Mannich Ketones, Eur. J. Med. Chem., 37, 803 (2002); https://doi.org/10.1016/S0223-5234(02)01404-6.
A. El-Masry, H. Fahmy and S.A. Abdelwahed, Synthesis and Antimi-crobial Activity of Some New Benzimidazole Derivatives, Molecules, 5, 1429 (2000); https://doi.org/10.3390/51201429.
J.R. Dimmock, S.C. Vashishtha, J.W. Quail, U. Pugazhenthi, Z. Zimpel, A.M. Sudom, T.M. Allen, G.Y. Kao, J. Balzarini and E. De Clercq, 4-(b-Arylvinyl)-3-(b-arylvinylketo)-1-ethyl-4-piperidinols and Related Compounds: A Novel Class of Cytotoxic and Anticancer Agents, J. Med. Chem., 41, 4012 (1998); https://doi.org/10.1021/jm9801455.
S. Bala, N. Sharma, A. Kajal, S. Kamboj and V. Saini, Mannich Bases: An Important Pharmacophore in Present Scenario, Int. J. Med. Chem., http://dx.doi.org/10.1155/2014/191072.
A. Gómez-Rivera, H. Aguilar-Mariscal, N. Romero-Ceronio, L.F. Roa-de la Fuente and C.E.Lobato-García, Bioorg. Med. Chem. Lett., 23, 5519 (2003); https://doi.org/10.1016/j.bmcl.2013.08.061.
F. Herencia, M.L. Ferrándiz, A. Ubeda, J.N. Domínguez, J.E. Charris, G.M. Lobo and M.J. Alcaraz, Synthesis and Anti-Inflammatory Activity of Chalcone Derivatives, Bioorg. Med. Chem. Lett., 8, 1169 (1998); https://doi.org/10.1016/S0960-894X(98)00179-6.
H.-H. Ko, L.-T. Tsao, K.-L. Yu, C.-T. Liu, J.-P. Wang and C.-N. Lin, Structure-Activity Relationship Studies on Chalcone Derivatives: The Potent Inhibition of Chemical Mediators Release, Bioorg. Med. Chem., 11, 105 (2003); https://doi.org/10.1016/S0968-0896(02)00312-7.
Y.-M. Lin, Y. Zhou, M.T. Flavin, L.-M. Zhou, W. Nie and F.-C. Chen, Chalcones and Flavonoids as Anti-Tuberculosis Agents, Bioorg. Med. Chem., 10, 2795 (2002); https://doi.org/10.1016/S0968-0896(02)00094-9.
S.N. Lopez, M.V. Castelli, S.A. Zacchino, J.N. Domínguez, G. Lobo, J. Charris-Charris, J.C.G. Cortés, J.C. Ribas, C. Devia, A.M. Rodríguez and R.D. Enriz, in vitro Antifungal Evaluation and Structure-Activity Relationships of a New Series of Chalcone Derivatives and Synthetic Analogues with Inhibitory Properties against Polymers of Fungal Cell Wall, Bioorg. Med. Chem., 9, 1999 (2001); https://doi.org/10.1016/S0968-0896(01)00116-X.
R. Li, G.L. Kenyon, F.E. Cohen, X. Chen, B. Gong, J.N. Dominguez, E. Davidson, G. Kurzban, R.E. Miller, E.O. Nuzum, P.J. Rosenthal and J.H. McKerrow, in vitro Antimalarial Activity of Chalcones and Their Derivatives, J. Med. Chem., 38, 5031 (1995); https://doi.org/10.1021/jm00026a010.
V.S. Parmar, N.K. Sharma, M. Husain, A.C. Watterson, J. Kumar, L.A. Samuelson, A.L. Cholli, A.K. Prasad, A. Kumar, S. Malhotra, N. Kumar, A. Jha, A. Singh, I. Singh, Himanshu, A. Vats, N.A. Shakil, S. Trikha, S. Mukherjee, S.K. Sharma, S.K. Singh, A. Kumar, H.N. Jha, C.E. Olsen, C.P. Stove, M.E. Bracke and M.M. Mareel, Synthesis, Characterization and in vitro Anti-Invasive Activity Screening of Polyphenolic and Heterocyclic Compounds, Bioorg. Med. Chem., 11, 913 (2003); https://doi.org/10.1016/S0968-0896(02)00539-4.
L.S. Pedroso, G.M. Fávero, L.E.A. De Camargo, R.M. Mainardes and N.M. Khalil, Effect of the o-Methyl Catechols Apocynin, Curcumin and Vanillin on the Cytotoxicity Activity of Tamoxifen, J. Enzyme Inhib. Med. Chem., 28, 734 (2013); https://doi.org/10.3109/14756366.2012.680064.
J. Zhang, L. Zhao, C. Zhu, Z. Wu, G. Zhang, X. Gan, D. Liu, J. Pan, D. Hu and B. Song, Facile Synthesis of Novel Vanillin Derivatives Incorp-orating a Bis(2-hydroxyethyl)dithhioacetal Moiety as Antiviral Agents, J. Agric. Food Chem., 65, 4582 (2017); https://doi.org/10.1021/acs.jafc.7b01035.
H. Korthou and R. Verpoorte, ed.: R.G. Berger, Vanilla, In: Flavours and Fragrances, Springer-Verlag, Berlin, vol. 1, pp. 203-217 (2007).