Design and Synthesis of New Series of One-Pot Schiff Base Ligands of 4-Aminobenzenesulfonamideas Potent Antibacterial and Antifungal Agents
Abstract
Schiff bases are imines formed by the condensation of a primary amine and a carbonyl compound. These classes of compounds are very important due to their wide range of biological activities and industrial applications. In this study, some Schiff base ligands (coded GAS1-5) were synthesized by condensation of 4Aminobenzenesulfonamide and some selected carbonyl molecules via MW irradiation for 1 minute at 385 watt power; and were characterized by FT-IR and elemental analyses. These Schiff bases were then evaluated for their bactericidal effects against two Gram positive and two Gram negative bacteria (Staphylococcus aureus, Bacillus subtilis and Escherichia coli, Pseudomonas aeruginosa respectively) and for their fungicidal activities against one fungus (Candida albicans). Their biocidal activities were also evaluated against one standard antibacterial drug, Zyprox (Ciprofloxacin), and one standard antifungal drug , Nizoral (ketoconazole), in the market. All the synthesized bases, except one, exhibited interesting antimicrobial activities against the selected microbes; some even exhibited better biocidal effects at the chosen concentration for this work (5M) than the standard commercial reference drugs used in this study.
Downloads
References
Zhaoqi Yang and Pinhua Sun (2006). Compare of three ways of synthesis of simple Schiff base. Molbank , 2006, M514 http://www.mdpi.org/molbank
Devidas,SM, Quadri, SH, Kamble, SA, Syed FM and Vyavhare, DY, (2011). Novel One-Pot Synthesis of Schiff Base Compounds Derived From Different Diamine & Aromatic Aldehyde Catalyzed by P2O5/SiO2 Under Free-Solvent Condition at Room Temperature. Journal of Chemical and Pharmaceutical Research, 3(2), 489-495.
Bhattacharya, A and Purohit, VC, (2003). Environmentally Friendly Solvent-Free Processes: Novel Dual Catalyst System in Henry Reaction. Organic Process Research and Development 7(3), 254–258 . DOI: 10.1021/op020222c
Mohamed , GG, Omar MM and Hindy, AM, (2006). Metal Complexes of Schiff Bases: Preparation, Characterization, and Biological Activity. Turkish Journal of Chemistry, 30, 361 – 382
Aziz HJ and Majed, HHA, (2011). Synthesis, Identification and Biological ActivitiesOf a New Series of Heterocyclic Amide. Wasit Journal for Science & Medicine , 4 (2), 44 – 53.
Asadi,M, Sepehrpour , H and Mohammadi, K, (2011). Tetradentate Schiff base ligands of 3,4- diaminobenzophenone:Synthesis, characterization and thermodynamics of complex formation with Ni(II), Cu(II) and Zn(II) metal ions. Journal of Serbian Chemical Society, 76 (1), 63–74. www.shd.org.rs/JSCS/
Abd El-Wahab, ZH and El-Sariag, MR, (2004). Derivatives of phosphate schiff base transition metal complexes: synthesis, studies and biological activity. Spectrochimica Acta partA: Molecular and Biomolecular Spectroscopy (Elsevier), 60(1-2), 271- 277.
Karvembu, R, Hemalatha, S, Prabhakaran, R and Natarajan, K, (2003). Synthesis, characterization and catalytic activities of ruthenium complexes containing triphenylphosphine / triphenylarsine and tetradentate Schiff bases. Inorganic Chemistry Communication 6(5), 486-490.
Mahalingam, V, Chitrapriya, N, Zeller, M and Natarajan, ( 2009). Ru(II)DMSO complexes containing aromatic and heterocyclic acid hydrazides: structure, electrochemistry and biological activity. Polyhedron, 28(8), 1532-1540,
Mahalingam, V, Chitrapriya, N,. Fronczek, F R and Natarajan, K, (2010). New Ru(II) DMSO complexes of ON/SN chelates: synthesis, behavior of Schiff bases towards hydrolytic cleavage of CN bond, electrochemistry and biological activities, Polyhedron, 29(18), 3363 -3371.
Bottcher, A, Takeuchi, T, Hardcastle, K1, Meade, T J and Gray, H B, (1997). Spectroscopy and electrochemistry of Cobalt(III) Schiff base complexes. Inorganic Chemistry, 36, 2498-2504.
Chandra, SS and Rathi, A, (2001). Magnetic and spectral studies on copper (II) complexes of N-O and N-S donor ligands. Journal of Saudi Chemical Society, 5(2), 175–182.
Neelakantan, MA , Esakkiammal, M, Mariappan, S S, Dharmaraja, J and Jeyakumar, T, ( 2010). Synthesis, characterization and biocidal activities of some Schiff base metal complexes. Indian Journal of Pharmaceutical Sciences,72(2), 216 222.
Chohan, ZH, Arif, M, Akhtar, MA and Supuran, C T, (2006). Metal-Based Antibacterial and Antifungal Agents: Synthesis, Characterization, and In-Vitro Biological Evaluation of Co(II), Cu(II), Ni(II), and Zn(II) Complexes With Amino Acid-Derived Compounds. Bioinorganic Chemistry and Applications, 2006, 1-13.
LopezSandoval, H, LondoiioLemos, ME, and GarzaVelasco, R, (2008). Synthesis, structure and biological activities of cobalt(II)and zinc(II) coordination compounds with 2- benzimidazole derivatives. Journal of Inorganic Biochemistry, 102(5-6), 1267-1276.
Nomiya, K, Yoshizawa, A, Tsukagoshi, N, Kasuga, NC, Hirakawa, S and Watanabe, J, (2004). Synthesis and structural characterization of silver(I), aluminium(III) and cobalt(II) complexes with 4- isopropyltropolone (hinokitiol) showing noteworthy biological activities. Action of silver(I) oxygen bonding complexes on the antimicrobial activities. Journal of Inorganic Biochemistry, 98(1), 46-60.
Fathalla, OA, Zeid, IF, Haiba, ME, Soliman, AM, Abd-Elmoez SI and El-Serwy WS, (2009). Synthesis, Antibacterial and Anticancer Evaluation of Some Pyrimidine Derivatives. World Journal of Chemistry .4(2),.127-132.
Jeewoth, T, Kam W, Li, H, Bhowon, MG, Ghoorohoo, MD and Babooram, K, (2000). Synthesis and anti-bacterial/catalytic properties of Schiff bases and Schiff base metal complexes derived from 2,3- diaminopyridine. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 30(6), 1023- 1038.
Liu, J, Cao, R, and Wu, Q, (2009). Synthesis and antibacterial evaluation of novel 4alkyl substituted phenyl ? aldehyde ketone derivatives. European Journal of Medicinal Chemistry, 44(4), 1737 - 1744..
Lv, J, Liu, T, Cai, S, Wang, X, Liu, L and Wang, Y, (2006). Synthesis, structure and biological activity of cobalt(II) and copper(II) complexes of valine derived schiff bases. Journal of Inorganic Biochemistry, 100(11), 1888-1896.
Dharmaraj, N, Viswanalhamurthi, P and Natarajan, K, (2001). Ruthenium(II) complexes containing bidentate Schiff bases and their antifungal activity. Transition Metal Chemistry, 26(2) 105 – 109.
Chandra, S, Raizada, S, Tyagi, M, and Gautam, A, (2007). Synthesis, Spectroscopic, and Antimicrobial Studies on Bivalent Nickel and Copper Complexes of Bis(thiosemicrbazone), Bioinorganic Chemistry and Applications, 2007, 1-7.
Weiqun, Z, Wen, Y, Liqun, X and Xianchen, C, (2005). N-Benzoyl-N -dialkylthiourea derivatives and their Co(III) complexes: structure, and antifungal,. Journal of Inorganic Biochemistry, 99(6), 1314-1319.
Kim, HJ, Chan, HL, Mahoney, N and Campbell, BC, (2011). Antifungal activity of redox-active benzaldehydes that target cellular antioxidation. Annals of Clinical Microbiology and Antimicrobials, 10, 23-39.
Jadhav, KP and Ingled, DB, (1983). Synthesis of 2,4-diary1-2,3-dihyrdo-1,5-benzothiazeoines and their 1,1-dioxides as antibacterial agents. Indian Journal of Chemistry, B22, 180.
Ajibade, P., 2008. Metal complexes in the management of parasitic diseases: In vitro
antiprotozoal studies of metal complexes of some antimalarial drugs. Current Science, 95, 1673.
Reddy, RJ, Ashok, D and Sharma, PN, (1993). Synthesis of 4,6-bis(2’-substitutcri-2-3’- dihydro-1.5- benzothiazepin-4’-yl) resorcinols as potential antifeedants. Indian Journal of Chemistry, B32, 404– 406..
Arayne, S, Sultana, N, Haroon, U and Mesaik, MA, (2009). Synthesis, Characterization, Antibacterial and Anti-Inflammatory Activities of Enoxacin Metal Complexes. Bioinorganic Chemistry and Applications, 2009, 1-6.
Satyanarayana, K and Rao, M.N.A.,(1993). Synthesis of 3-[4-[2t 3-dihydro-2-(substituted aryl)-1,5- benzothiazcpin-4-yl]phcnyl]sydnones as potential anti-inflammatory agents,. Indian Journal of Pharmaceutical Sciences, 55, 230–233.
Bhatewara, A, Rao Jetti, S, Kadre, T, Paliwal, P and Jain, S, ( 2013). Microwave-Assisted Synthesis and Biological Evaluation of Dihydropyrimidinone Derivatives as Anti-Inflammatory, Antibacterial, and Antifungal Agents. International Journal of Medicinal Chemistry, 2013. Article ID 197612, 5 pages; http://dx.doi.org/10.1155/2013/197612.
Fahmideh, S., Lotf, A.S and Shahriar, G., 2010. Synthesis, characterization and anti- tumour activity of Fe(III) Schiff base complexes with unsymmetric tetradentate ligands. Bulletin of the Chemical Society of Ethiopia, 24, 193-199.
Ferrari, MB, Capacchi, S, Pelosi, G, Reffo, G, Tarasconi, P, Alberlini, R, Pinelli, S and Lunghi, P, (1999). Synthesis, structural, characterization and biological activity of helicin thiosemicarbazone Monohydrate and a copper(ll)complex of salicylaldehyde thiosemi Carbazone. Inorganica Chimica Acta, 286(2), 134 – 141.
Mahalingam, V, Chitrapriya, N, Fronczek, FR and Natarajan, K, (2008). New Ru(II)dmso complexes with heterocyclic hydrazine ligands towards cancer chemotherapy. Polyhedron, 27(7), 1917-1924.
Varadinova, T, Kovala-Demertzi, D, Rupelieva, M, De-mertzis, M and Genova, P, (2001). Antiviral activity of platinum (II) and palladium (II) complexes of pyridine-2 - carbaldehydethiosemicarbazone, Acta Virologica, 45(2), 87–94.
Pandeya, SN, Raja, AS and Stables, JP, (2002). Synthesis of isatin semicarbazones as novel anticonvulsants-role of hydrogen bonding. Journal of Pharmacy and Pharmaceutical Sciences, 5(3), 266–271.
Pandeya, SN and Rajput, N, (2012). Synthesis and Anticonvulsant Activity of Various Mannich and Schiff Bases of 1,5-Benzodiazepines. International Journal of Medicinal Chemistry, 2012. Article ID 237965, 10 pages; doi:10.1155/2012/237965
De Sarro, G, Chimirri, A, Desaro, A, Gitto, R.,Grasso, S., Giusti P. and Chapman, AG, (1995). GYKI 52466 and related 2,3-benzodiazepines as anticonvulsant agents in DBA/2 mice. European Journal of Pharmacology, 294(2-3), 411-422.
Sharma, B., Verma, A., Prajapati, S and Sharma, U.K., 2013. Synthetic Methods, Chemistry, and the Anticonvulsant Activity of Thiadiazoles. International Journal of Medicinal Chemistry, 2013, Article ID 348948, 16pages;http://dx.doi.org/10.1155/20 13/348948.
Sondhi, SM, Dinodia, M and Kumar, A, (2006). Synthesis, anti-inflammatory and analgesic activity evaluation of some amidine and hydrazone derivatives. Bioorganic andMedicinal Chemistry, 14, 4657-4663..
Nfor, EN, Esemu, SN, Ayimele, GA., Eno, EA, Iniama, GE and Offiong, OE, (2011). Synthesis, stereochemistry and antimicrobial activity of copper(II) and nickel(II) complexes of 4 - phenylsemicarbazones. Bulletin Chemical Society of Ethiopia, 25(3), 361-370.
Mishra,AP, Hwari, A, Gupta, SK. and Jain, R, (2012). Synthesis, spectral and antimicrobial studies of some Co(II), Ni(II) and Cu(II) complexes containing 2-thiophenecarboxaldehyde moiety. E-Journal of Chemistry, 9(3), 1113-1121.
Issa, RM, Khedr AM and Rizk, H, (2008). H NMR, IR and UV/VIS spectroscopic studies of some Schiff bases derived from 2 aminobenzothiazole and 2 amino 3 hydroxypyridine. Journal of the Chinese Chemical Society, 55(4), .875-884.
Bellu, S, Trape, M, Trossero, C, Molina, G, Drogo, C, Williams, P, Atria, AM, Munoz, JC and Zacchino, S, (2003). Synthesis, structure and antifungal properties of Co(II)sulfathiazolate complexes, Quim. Nova, 6, 188.
Hammuel, C, Yebpella, GG, Shallangwa, GA, Magomya, AM and Agbaji, AS, (2011. Phytochemical And Antimicrobial Screening Of Methanol And Aqueous Extracts Of Agave Sisalana, Acta Poloniae Pharmaceutica Ñ Drug Research, 68(4), 535-539.
Yebpella. GG., Hammuel, C, Adeyemi Hassan, M.M, Magomya, AM., Agbaji, AS and Shallangwa, GA, (2011). Phytochemical screening and a comparative study of antibacterial activity of Aloe vera green rind, gel and leaf pulp extracts, International Research Journal of Microbiology, 2(10), 382-386.
Copyright (c) 2015 Journal of Progressive Research in Chemistry
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
