Synthesis of New Unsymmetrical Schiff Bases as Potential Antimicrobial Agents

Year 2020, Volume: 5 Issue: 1, 13 - 25, 18.06.2020

Dilek Nartop , Hatice Öğütcü

https://doi.org/10.33484/sinopfbd.640297

Cited By: 1

Abstract

Novel unsymmetrical Schiff bases (L_3a-L_3c) were synthesized by using a two-stage method. The starting Schiff bases were prepared by the reaction of 2-aminophenol (or 2-amino-4-methylphenol or 2-amino-4-chlorophenol) with 1-nitro-2-naphthaldehyde. In these compounds, the nitro groups were reduced to amino groups using selective reducing agent and then 2-hydroxybenzaldehyde were added. Thus, three new unsymmetric Schiff base ligands were obtained. The antimicrobial activity of the synthesized unsymmetric Schiff bases were evaluated against some pathogenic strains (Shigella dysenteria type 7, Listeria monocytogenes 4b, Escherichia coli, Salmonella typhi H, Staphylococcus epidermis, Brucella abortus, Micrococcus luteus, Bacillus cereus sp., Pseudomonas putida sp.) and yeast (Candida albicans).

Keywords

Unsymmetrical Schiff base, Reducing Agent Na2S2O4, Antimicrobial Activity

Supporting Institution

Nevşehir Hacı Bektaş Veli University Research Foundation

Project Number

2010/17

Potansiyel Antimikrobiyal Ajanlar Olarak Yeni Asimetrik Schiff Bazlarının Sentezi

Abstract

Yeni asimetrik Schiff
bazları (L_3a-L_3c) iki aşamalı bir yöntem
kullanılarak sentezlendi. 2-aminofenol (veya 2-amino-4-metilfenol veya
2-amino-4-klorofenol) ile 1-nitro-2-naftaldehitin reaksiyonundan başlangıç
Schiff bazları hazırlandı. Seçici indirgeyici ajan kullanılarak bileşiklerdeki nitro
grupları amino gruplarına indirgendi ve 2-hidroksibenzaldehit eklendi. Böylece,
üç yeni asimetrik Schiff baz ligandı elde edildi. Sentezlenen asimetrik Schiff
bazlarının antimikrobiyal aktiviteleri, bazı patojenik suşlar (Shigella dysenteria
type 7, Listeria monocytogenes 4b, Escherichia coli, Salmonella typhi H,
Staphylococcus epidermis, Brucella abortus, Micrococcus luteus, Bacillus cereus
sp., Pseudomonas putida sp.) ve maya (Candida
albicans) karşısında değerlendirildi.

Keywords

Asimetrik Schiff bazı, İndirgeyici ajan Na2S2O4, Antimikrobiyal aktivite

Project Number

2010/17

References

• References[1] Anand P, Patil VM, Sharma VK, Khosa RL, Masand N, 2012. Schiff bases: A review on biological insights, Int J Drug Discov. 3:851-868.
• [2] Cleiton M, Daniel LS, Luzia VM, Rosemeire BA, Maria AR, Cleide VBM, Angelo F, 2011. Schiff bases: A short review of their antimicrobial activities, J Adv Res. 2:1-8.
• [3] Arulmurugan S, Kavitha HP, 2010. Venkatraman BR. Biological activities of Schiff base and its complexes: A review, Rasayan J. Chem. 3:385-410.
• [4] Ali OAM, El-Medani SM, Serea MRA, 2015. Sayed AS. Unsymmetrical Schiff base (ON) ligand on complexation with some transition metal ions: Synthesis, spectral characterization, antibacterial, fluorescence and thermal studies, Spectrochim Acta A Mol Biomol Spectrosc. 136:651-660.
• [5] Abdel-Gaber AM, Masoud MS, Khalil EA, Shehata EE, 2009. Electrochemical study on the effect of Schiff base and its cobalt complex on the acid corrosion of steel, J Corros Sci. 51:3021-3024.
• [6] Saghatforoush LA, Chalabian F, Aminkhani A, Karimnezhad G, Ershad S, 2009. Synthesis, spectroscopic characterization and antibacterial activity of new cobalt(II) complexes of unsymmetrical tetradentate (OSN2) Schiff base ligands, Eur J Med Chem. 44:4490-4495.
• [7] Dwyer FB, Mayhew E, Roe EMF, Shulmon A, 1965. Inhibition of landschütz ascites tumour growth by metal chelates derived from 3,4,7,8-tetramethyl-1,10-phenanthroline. Br J Cancer, 19:195-199.
• [8] Zoubi WA, 2013. Biological activities of Schiff bases and their complexes: A review of recent Works, Int. J. Org. Chem. 3, 73-95.
• [9] Balsells J, Mejorado L, Phillips M, Ortega F, Aguirre G, Somanathan R, Walsh PJ, 1998. Synthesis of chiral sulfonamide/Schiff base ligands. Tetrahedron Asymmetry, 9:4135-4142.
• [10] Isloor AM, Kalluraya B, Shetty P, 2009. Regioselective reaction: Synthesis, characterization and pharmacological studies of some new mannich bases derived from 1,2,4-triazoles, Eur. J. Med. Chem. 44:3784-3787.
• [11] Rudbari HA, Khorshidifard M, Askari B, Habibi N, Bruno G, 2015. New asymmetric Schiff base ligand derived from allylamine and 2,3-dihydroxybenzaldehyde and its molybdenum(VI) complex: Synthesis, characterization, crystal structures, computational studies and antibacterial activity together with synergistic effect against Pseudomonas Aeroginosa PTTC 1570, Polyhedron 100:180-191.
• [12] Abo-Aly MM, Salem AM, Sayed MA, Abdel Aziz AA, 2015. Spectroscopic and structural studies of the Schiff base 3-methoxy-N-salicylidene-o-amino phenol complexes with some transition metal ions and their antibacterial, antifungal activities, Spectrochim. Acta Part A, 136:993-1000.
• [13] Zayed EM, Zayed MA, 2015. Synthesis of novel Schiff's bases of highly potential biological activities and their structure investigation, Spectrochim. Acta A Mol. Biomol. Spectrosc. 143:81-90.
• [14] Gupta SD, Snigdha D, Mazaira GI, Galigniana MD, Subrahmanyam CVS, Gowrishankar NL, Raghavendra NM, 2014. Molecular docking study, synthesis and biological evaluation of Schiff bases as Hsp90 inhibitors, Biomed. Pharmacother. 68:369-376.
• [15] Alaghaz AMA, Zayed ME, Alharbi SA, 2015. Synthesis, spectral characterization, molecular modeling, biological activity and potentiometric studies of 4-amino-5-mercapto-3-methyl-S-triazole Schiff’s base complexes, J. Mol. Struct. 1083:430-440.
• [16] Avila-Sorrosa A, Hernandez-Gonzalez JI, Reyes-Arellano A, Toscano RA, Reyes-Martinez R, Pioquinto-Mendoza JR, Morales-Morales D, 2015. Synthesis, structural characterization and biological activity of fluorinated Schiff-bases of the type [C6H4-1-(OH)-3-(CH=NArF)], J. Mol.Struct. 1085:249-257.
• [17] Dhar DN, Taploo CL, 1982. Schiff bases and their applications, J. Sci. Ind. Res. 41:501-506.
• [18] Sarı N, Pişkin N, Öğütcü H, and Yetim NK, 2012. Spectroscopic characterization of novel d-aminoacid-Schiff bases and their Cr(III) and Ni(II) complexes as antimicrobial agents, Med. Chem. Res. 22:580-587.
• [19] Yang J, Shi R, Zhou P, Qiu Q, Li H, 2016. Asymmetric Schiff bases derived from diaminomaleonitrile and their metal complexes, J. Mol. Struct. 1106:242-258. [20] Ray A, Maity D, Pramanik A, Das KK, Nandi M, Bhaumik A, Nethaji M, Mondal S, Mukherjee M, Ali M, 2009. Two highly unsymmetrical tetradentate (N3O) Schiff base copper(II) complexes: Template synthesis, structural characterization, magnetic and computational studies, Polyhedron 28:3659-3666. [21] Meghdadi S, Amirnasr M, Mereiter K, Molaee H, Amiri A, 2011. Synthesis, structure and electrochemistry of Co(III) complexes with an unsymmetrical Schiff base ligand derived from 2-aminobenzylamine and pyrrole-2-carboxaldehyde, Polyhedron 30:1651-1656.
• [22] Kim GJ, Shin JH, 1999. Application of new unsymmetrical chiral Mn(III), Co(II,III) and Ti(IV) salen complexes in enantioselective catalytic reactions, Catal. Lett. 63:83-90.
• [23] Kwok CC, Yu SC, Sham IHT, Che CM, 2004. Self-assembled zinc(II) Schiff base polymers for applications in polymer light-emitting devices, Chem. Commun. 23:2758-2759.
• [24] Behpour M, Ghoreishi SM, Soltani N, Niasari MS, 2009. The inhibitive effect of some bis-N,S-bidentate Schiff bases on corrosion behaviour of 304 stainless steel in hydrochloric acid solution, J. Corros. Sci. 51:1073-1082. [25] Nartop D, Gürkan P, Sarı N, Çete S, 2008. Tetradentate asymmetric Schiff bases and their Ni(II) and Fe(III) complexes, J. Coord. Chem. 61:3516-3524.
• [26] Güngör Ö, Gürkan P, 2010. Synthesis and spectroscopic properties of novel asymmetric Schiff bases, Spectrochim. Acta A Mol. Biomol. Spectrosc. 77:304-311.
• [27] Nartop D, Gürkan P, 2013. Synthesis, characterization and antibacterial activities of unsymmetric diimine Schiff bases and their Fe(III) and Ni(II) complexes, Chinese J. Inorg. Chem. 6:1227-1234.
• [28] Güngör Ö, Gürkan P, 2015. Potentiometric and antimicrobial studies on the asymmetric Schiff bases and their binuclear Ni(II) and Fe(III) complexes; Synthesis and sharacterization of the complexes, Arab. J. Chem. DOI: 10.1016/j.arabjc.2015.02.009.
• [29] Özdemir Ö, 2016. Novel symmetric diimine-Schiff bases and asymmetric triimine-Schiff bases as chemosensors for the detection of various metal ions, J. Mol. Struct. 1125:260-271.
• [30] Nartop D, Özdemir Ö, Gürkan P, 2017. Synthesis, characterization and investigation of tautomeric, potentiometric and antimicrobial properties of a novel unsymmetric Schiff base and its Fe(III) and Ni(II) complexes, Mor. J. Chem. 5:560-572.
• [31] Güngör Ö, 2017. Intramolecular proton transfer equilibrium in salicylidene- and naphthalene-based tetraimine Schiff bases, GU J. Sci. 30:191-214.
• [32] Nartop D, Clegg W, Harrington RW, Henderson RA, Will, CY, 2014. Binding multidentate ligands to Ni2+: Kinetic identification of preferential binding sites, Dalton Trans. 43:3372-3382.
• [33] Koçoğlu S, Öğütcü H, Hayvalı Z, 2019. Photophysical and antimicrobial properties of new double‑armed benzo‑15‑crown‑5 ligands and complexes, Res. Chem. Intermediat. doi.org/10.1007/s11164-019-03741-3.
• [34] Ehling-Schulz M, Fricker M, Grallert H, Rieck P, Wagner M, Scherer S, 2006. Cereulide synthetase gene cluster from emetic Bacillus cereus: Structure and location on a mega virulence plasmid related to Bacillus anthracis toxin plasmid pXO1, BMC Microbiol. 6:20.
• [35] Zayed EM, Zayed MA, El-Desawy M, 2015. Preparation and structure investigation of novel Schiff bases using spectroscopic, thermal analyses and molecular orbital calculations and studying their biological activities, Spectrochim. Acta A Mol. Biomol. Spectrosc. 134:155-164.
• [36] Dada EO, Aruwa CE, 2014. Microorganisms associated with urine contaminated soils around lecture theatres in Federal University of Technology, Akure, Nigeria, Int. J. Appl. Microbiol. Biotechnol. Res. 2:79-85. [37] Kabir MA, Hussain MA, Ahmad Z, 2012. Candida albicans: A model organism for studying fungal pathogens, ISRN Microbiol. doi: org/10.5402/2012/538694.
• [37] Kabir MA, Hussain MA, Ahmad Z, 2012. Candida albicans: A model organism for studying fungal pathogens, ISRN Microbiol. doi: org/10.5402/2012/538694.
• [38] Matilde F, Mario P, Jesús de la T, Molina-Henares MA, Abdelali D, María AL, Amalia R, Victor C, Ingrid G, Juan LR, Miguel A, Estrella D, 2015. Analysis of the pathogenic potential of nosocomial Pseudomonas putidastrains, Front. Microbiol. 6: 871.