Synthesis of diazole-thiols derivatives from L-Cysteine: Characterization, complex formation with Ni(II), Cu(II) and evaluation of their antibacterial activity

作者: Adil Ali Othman , Mokhtar Boualem Lahrech , Mouna Souad Abbassi , Khaled Briki

DOI: 10.1016/J.JSCS.2021.101230

关键词: Biological activityAntibacterial activityDiazolePseudomonasBacteriaMicroorganismChemistryCysteineNuclear chemistryEscherichia coli

摘要: Abstract Four novel diazole-thiol derivatives namely: 5-(1-amino-2-sulfanylethyl)-1,3,4-oxadiazole-2(3H)-thione 6, 4-amino-5-(1-amino-2-sulfanylethyl)-4H-1,2,4-triazole-3-thiol 7, 1-amino-3-(1-amino-2-sulfanylethyl)-1H-1,2,4-triazole-5-thiol 8, and 5-(1-amino-2-sulfanylethyl)-1H-1,2,4-triazole-3-thiol 9 have been synthesized from l-Cysteine characterized by IR, 1H-NMR, 13C-NMR GC-MS. Complex formation with Ni(II) Cu(II) ions four of were formed isolated. The final synthetic products (6-9) their corresponding complexes (6a,a’-9a,a’) tested against Gram-negative bacteria: Escherichia coli, Pseudomonas aeroginosae Gram-positive Staphylococus aureus 25923 showed no biological activity. While 7-9 exhibited appreciable activity microorganisms. outstanding results is that the Cu(II)-complexes 8a’and 9a’ (MIC) on similar organisms at very low concentrations (5µg/ml) which in fact lower concentration than what had reported other relative compounds.

参考文章(36)
Kyoung-Soon Jang, Roger R. Nani, Anastasia Kalli, Sergiy Levin, Axel Müller, Sonja Hess, Sarah E. Reisman, William M. Clemons, A cationic cysteine-hydrazide as an enrichment tool for the mass spectrometric characterization of bacterial free oligosaccharides Analytical and Bioanalytical Chemistry. ,vol. 407, pp. 6181- 6190 ,(2015) , 10.1007/S00216-015-8798-8
Marcelle B.M. Spera, Frederico A. Quintão, Diego K.D. Ferraresi, Wilton R. Lustri, Alviclér Magalhães, André L.B. Formiga, Pedro P. Corbi, Palladium(II) complex with S-allyl-l-cysteine: New solid-state NMR spectroscopic measurements, molecular modeling and antibacterial assays Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. ,vol. 78, pp. 313- 318 ,(2011) , 10.1016/J.SAA.2010.10.012
László Galgóczy, Laura Kovács, Krisztina Krizsán, Tamás Papp, Csaba Vágvölgyi, Inhibitory effects of cysteine and cysteine derivatives on germination of sporangiospores and hyphal growth of different Zygomycetes. Mycopathologia. ,vol. 168, pp. 125- 134 ,(2009) , 10.1007/S11046-009-9204-X
Krishna Kumar Gnanasekaran, Baskar Nammalwar, Maeghan Murie, Richard A. Bunce, Efficient synthesis of 1,3,4-oxadiazoles promoted by NH4Cl Tetrahedron Letters. ,vol. 55, pp. 6776- 6778 ,(2014) , 10.1016/J.TETLET.2014.10.028
Stéphane Octave, Bénigne-Ernest Amborabé, Estelle Luini, Thierry Ferreira, Pierrette Fleurat-Lessard, Gabriel Roblin, Antifungal effects of cysteine towards Eutypa lata, a pathogen of vineyards Plant Physiology and Biochemistry. ,vol. 43, pp. 1006- 1013 ,(2005) , 10.1016/J.PLAPHY.2005.10.003
S.A SALLAM, E.S.I IBRAHIM, M.I ANWAR, SYNTHESIS, COMPLEXATION AND BIOLOGICAL ACTIVITY OF NEW ISATIN SCHIFF_BASES Journal of The Chilean Chemical Society. ,vol. 57, pp. 1482- 1491 ,(2012) , 10.4067/S0717-97072012000400030
Roman M. Balabin, Conformational equilibrium in alanine: Focal-point analysis and ab initio limit Computational and Theoretical Chemistry. ,vol. 965, pp. 15- 21 ,(2011) , 10.1016/J.COMPTC.2011.01.008
C.A McAuliffe, S.G Murray, Metal complexes of sulphur-containing amino acids Inorganica Chimica Acta Reviews. ,vol. 6, pp. 103- 121 ,(1972) , 10.1016/0073-8085(72)80013-5
Naveen Vasudev Kulkarni, Srinivasa Budagumpi, Gurunath Suresh Kurdekar, Vidyanand Krishna Revankar, Suresh Didagi, Anticonvulsant Activity and Toxicity Evaluation of Cu II and Zn II Metal Complexes Derived from Triazole-Quinoline Ligands Chemical & Pharmaceutical Bulletin. ,vol. 58, pp. 1569- 1575 ,(2010) , 10.1248/CPB.58.1569