Two novel dopamine hydrochloride Schiff bases (E)-4-(2-((4-hydroxy-2H-chromen-2-ylidene)amino)ethyl)benzene-1,2-diol (1) and (E)-3-((3,4-dihydroxyphenethyl)imino)indolin-2-one (2) have been synthesized using isatin and 4-hydroxycoumarin. The prepared compounds have been characterized by solubility in different solvents, melting point determination, elemental analysis, FT-IR, 1H-NMR, 13C-NMR and powder X-ray diffraction spectroscopic techniques, with the structures of the Schiff bases proposed. The proposed structures of the compounds have been optimized using the Spartan program so as to get the most stable conformers. The synthesized Schiff bases have been tested for their biological activity against two Gram positive bacteria; Staphylococcus aureus, Bacillus subtilis, and two Gram negative bacteria; Klebsiella pneumoniae and Escherichia coli with their minimum inhibition concentration (MIC) values determined. The Schiff base 1 was found to inhibit E. coli and K. pneumonia with MIC values of 3.12 and 6.25 μg/mL, followed by K. pneumonia compared to the reference standards with MIC values of 3.12 μg/ml indicating that 1 could be a potential lead compound.
References
[1]
Bozarth, M.A. (2017) Dopaminergic Pathways and Addiction. In: Wenzel, A.E., Ed., The Sage Encyclopedia of Abnormal and Clinical Psychology, Sage Publications, Thousand Oaks, 1178-1182.
[2]
Grace, A.A. (2000) The Tonic/Phasic Model of Dopamine System Regulation and Its Implications for Understanding Alcohol and Psychostimulant Craving. Addiction, 95, S119-S128.
[3]
LaVoie, M.J., Ostaszewski, B.L., Weihofen, A., Schlossmacher, M.G. and Selkoe, D.J. (2005) Dopamine Covalently Modifies and Functionally Inactivates Parkin. Nature Medicine, 11, 1214-1221. https://doi.org/10.1038/nm1314
[4]
Khan, S.A., Asiri, A.M., Basheike, A.A. and Sharma, K. (2013) Green Synthesis of Novel Pyrazole Containing Schiff Base Derivatives as Antibacterial Agents on the Bases of in-Vitro and DFT. European Journal of Chemistry, 4, 454-458. https://doi.org/10.5155/eurjchem.4.4.454-458.784
[5]
Teuber, M. (2001) Veterinary Use and Antibiotic Resistance. Current Opinion in Microbiolology, 4, 493-499. https://doi.org/10.1016/S1369-5274(00)00241-1
[6]
da Silva C.M., da Silva D.L., Modolo L.V., Alves R.B., de Resende M.A., Martins C.V.B. and de Fátima A. (2011) Schiff Bases: A Short Review of Their Antimicrobial Activities. Journal of Advanced Research, 2, 1-8. https://doi.org/10.1016/j.jare.2010.05.004
[7]
Mohini, Y., Prasad, R.B.N., Karuna, M.S.L., Kumar, C.G., Poornima, M. and Sujitha, P. (2013) Synthesis of Fatty Acid Schiff Base Esters as Potential Antimicrobial and Chemotherapeutic Agents. Medicinal Chemistry Research, 22, 4360-4366. https://doi.org/10.1007/s00044-012-0450-y
[8]
Shi, L., Ge, H.-M., Tan, S.-H., Li, H.-Q., Song, Y.-C., Zhu, H.-L. and Tan, R.-X. (2007) Synthesis and antimicrobial activities of Schiff bases derived from 5-chlorosalicylaldehyde. European Journal of Medicinal Chemistry, 42, 558-564. https://doi.org/10.1016/j.ejmech.2006.11.010
[9]
Cheng, L.-X., Tang, J.-J., Luo, H., Jin, X.-J., Dai, F., Yang, J., Qian, Y.-P., Li, X.-Z. and Zhou, B. (2010) Antioxidant and Antiproliferativeactivities of Hydroxylsubstituted Schiff Bases. Bioorganic & Medicinal Chemistry Letters, 20, 2417-2420. https://doi.org/10.1016/j.bmcl.2010.03.039
[10]
Bayeh, Y., Mohammed, F., Gebrezgiabher, M., Elemo, F., Getachew, M. and Thomas, M. (2020) Synthesis, Characterization and Antibacterial Activities of Polydentate Schiff Bases, Based on Salicylaldehyde. Advances in Biological Chemistry, 10, 127-139. https://doi.org/10.4236/abc.2020.105010
[11]
Toh-Boyo, G.M., Njong, R.N., Babette, E.M. and Nfor, E.N. (2021) Synthesis, Spectroscopic, Molecular Modeling and Anti-Fungal Studies of Some Divalent Metal Complexes of 4-Hydroxyacetophenone Isonicotinoyl Hydrazone. Open Journal of Inorganic Chemistry, 11, 95-109. https://doi.org/10.4236/ojic.2021.113007
[12]
Nfor, E.N., Husian, A., Majoumo-Mbe, F., Njah, I.N., Offiong, E.O. and Bourne, S.A. (2013) Synthesis, Crystal Structure and Antifungal Activity of Ni(II) Complex of a New Hydrazone Derived from Anti-Hypertensive Drug Hydralazine Hydrochloride. Polyhedron, 63, 207-213. https://doi.org/10.1016/j.poly.2013.07.028
[13]
Mikwa, C.C., Toh-Boyo, G.M., Njong, R.N., Ndosiri, B.N., Ndamyabera, C.A., Katsuumi, N., Mitani, Y., Nfor, E.N. and Akitsu, T. (2022) Bivalent Metal Complexes of a Novel Modified Nicotinic Acid Hydrazide Drug: Synthesis, Characterization and Anti-Tubercular Studies. European Journal of Chemistry, 13, 63-68.
[14]
Hehre, W.J. and Ohlinger, W.A. (2014) Spartan’14. Wavefunction, Inc, Irvine.
[15]
Stewart, J.J.P. (1991) Optimization of Parameters for Semi-Empirical Methods. III Extension of PM3 to Be, Mg, Zn, Ga, Ge, As, Se, Cd, In, Sn, Sb, Te, Hg, Tl, Pb, and Bi. Journal of Computational Chemistry, 12, 320-341. https://doi.org/10.1002/jcc.540120306
[16]
Goto, S., Jo, K., Kawakita, T., Mitsuhashi, S., Nishino, T., Ohsawa, N.and Tanami, H. (1981) Determination Method of Minimum Inhibitory Concentrations. Chemotherapy, 29, 76-79.
[17]
Winter, C.A., Risley, E.A. and Nuss, G.W. (1962) Carrageenin-Induced Edema in Hind Paw of the Rat as an Assay for Anti-Inflammatory Drugs. Proceedings of the Society for Experimental Biology and Medicine, 111, 544-547.
[18]
Majoumo-Mbe, F., Nfor, E.N., Sengeh, E.B., Njong, R.N. and Offiong E.O. (2015) Synthesis, Crystal Structure and Biological Activity of 1-(phthalazin-1(2H)-one) [(Pyridin-2-yl) ethylidene] Hydrazone and Its Cobalt (III) Complex. Communications in Inorganic Synthesis, 3, 40-46.
[19]
Nfor, E.N., Esemu, S.N., Ayimele, G.A., Eno, E.A., Iniama, G.E. and Offiong, E.O. (2011) Copper (II) and Nickel (II) Complexes of 4-Phenylsemicarbazones: Synthesis, Stereochemistry and Antimicrobial Activity. Bulletin of the Chemical Society of Ethopia, 25, 361-370. https://doi.org/10.4314/bcse.v25i3.68668
[20]
Sumrra, S.H., Ibrahim, M., Ambreen, S., Imran, M., Danish, M. and Rehmani, F.S. (2014) Synthesis, Spectral Characterization, and Biological Evaluation of Transition Metal Complexes of Bidentate N, O Donor Schiff Bases. Bioinorganic Chemistry and Applications, 2014, Article ID: 812924. https://doi.org/10.1155/2014/812924
[21]
Asiri, A.M. and Khan, S.A. (2010) Synthesis and Anti-Bacterial Activities of Some Novel Schiff Bases Derived from Aminophenazone. Molecules, 15, 6850-6858. https://doi.org/10.3390/molecules15106850
[22]
Nakamoto, K. (1978) Infrared and Raman Spectra of Inorganic and Coordination Compounds. Part B: Theory and Applications. John Wiley & Sons, Ltd., Hoboken, 156 p.
[23]
Yong, J.N., Majoumo-Mbe, F., Samje, M. and Nfor, E.N. (2016) Synthesis, Molecular Structure and Anti-Onchocercal Studies of 1-(Phthalazin-1(2H)-one) [(Pyridin-2-yl) ethylidene] Hydrazone. International Journal of Organic Chemistry, 6, 77-84. https://doi.org/10.4236/ijoc.2016.61008
[24]
Silverstein, R.M., Webster, F.X. and Kiemle, D.J. (2005) Spectrometric Identification of Organic Compounds. 7th Edition, John Wiley & Sons, Inc., Hoboken.
[25]
Pavia, D.L., Lampman, G.M. and Kriz, G.S. (2001) Introduction to Spectroscopy. Third Edition, Thomson Learning, Inc., Toronto, 579.
[26]
Nfor, E.N., Burrows, A.D., Ndosiri, B.N., Keenan, L.L. and Offiong, E.O. (2019) Synthesis, Structure and Hydrogen Sorption Properties of a Pyrazine-Bridged Copper(I) Nitrate Metal-Organic Framework. European Journal of Chemistry, 10, 195-200. https://doi.org/10.5155/eurjchem.10.3.195-200.1888
[27]
Guha, R. and Willighagen, E. (2012) A Survey of Quantitative Descriptions of Molecular Structure. Current Topics in Medicinal Chemistry, 12, 1946-1956. https://doi.org/10.2174/156802612804910278
