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I In nt t. . J J. . B Bi io op ph ha ar rm ma a R Re es se ea ar rc ch h ISSN: 2287-6898 Review Article Corresponding Author: K. Sandeep rajan C.R.R. College of Pharmacy Eluru-534007 West Godavari DT Andhra Pradesh India. Page| 163 MULTI FACET APPLICATONS OF SCHIFF BASE AND ITS DERIVATIVES Sandeep rajan K. K. Tejaswi K. Mohini kalyani P. Mukhurji and P. Vinod kumar C.R.R. College of Pharmacy Eluru-534007 West Godavari DT Andhra Pradesh Received for publication: June 5 th 2013 Revised: July 25 th 2013 Accepted: July 30 th 2013 Introduction Schiff bases derived from an amino and carbonyl compound are an important class of ligands that Coordinate to metal ions via azomethine nitrogen and have been studied extensively 1 . In azomethine derivatives the CN linkage is essential for biological activity several azomethine has been reported to possess remarkable antibacterial antifungal anticancer and antimalarial activities 2-3 . The complexes of copper with Schiff bases have wide applications in food industry dye industry analytical chemistry Catalysis fungicidal agrochemical anti-inflammable activity antiradical activities and biological activities 4 . Schiff-base complexes are considered to be among the most important stereo chemical models in main group and transition metal coordination chemistry due to their preparative accessibility and structural variety 5 . Copper II complexes show distorted octahedral and tetrahedral symmetries due to d9 configuration John-Teller effect. The distortion is usually seen as axial elongation consistent with the liability and geometric flexibility of the complex. Therefore typical Cu II complexes have square planar or square pyramidal geometries with weakly associated ligands in the axial position s but some copper II complexes possess trigonal bipyramidal geometry. The fundamental role of copper and the recognition of its complexes as important bioactive compounds in vitro and in vivo aroused an ever-increasing interest in these agents as potential drugs for therapeutic intervention in various diseases. The vast array of information available for their bioinorganic properties and mode of action in several biological systems combined with the new opportunities offered by the flourishing technologies of medicinal chemistry is creating an exciting scenario for the development of a novel generation of highly active drugs with minimized side effects which could add significantly to the current clinical research and practice. A considerable number of Schiff’s base copper complexes have potential biological interest being used as more or less successful models of biological compounds 6 . Not only they have played a seminal role in the development of modern coordination chemistry but also they can also be found at key points in the development of inorganic biochemistry catalysis and optical materials 7 . In this review the pharmacological potential of several heterocyclic scaffolds pharmacophores and their combined biological effect with an active moiety i.e. imines - CHN- have been extensively studied. Reactions involved in the formation of Schiff bases: A Schiff base is a nitrogen analog of an aldehyde or ketone in which the CO group is replaced by CN-R group. It is usually formed by condensation of an aldehyde or ketone with a primary amine according to the following scheme fig1. Fig.1: Condensation of aldehyde or ketone with a primary amine. Where R may be an alkyl or an aryl group. Schiff bases that contain aryl substituent’s are substantially more stable and more readily synthesized while those which contain alkyl substituent’s are relatively unstable. Schiff bases of aliphatic aldehydes are relatively unstable and readily polymerizable while Abstract: Schiff bases are versatile ligands which are synthesized from the condensation of an amino compound with carbonyl compounds. These compounds and their metal complexes play a prominent role as catalysts in various biological metabolisms and in polymers dyes and medicinal and pharmaceutical fields. Wide possibility as an O2 detector is also outlined. This review summarizes the applications of Schiff bases and their complexes. Coordination chemistry employs Schiff bases which have achieved prime importance in this era. The extensive studies have been conducted on complexation of Schiff bases with metals due to the attractive physicochemical properties of metal complexes and broad range of utilization in various areas of science. Keywords: Schiff bases metal complexes Catalytic properties ligands.

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Sandeep Rajan et al.: Int. J. Biopharma Research 2013 02 08 163-170 Page | 164 those of aromatic aldehydes having effective conjugation are more stable 8-10 . The formation of a Schiff base from an aldehydes or ketones is a reversible reaction and generally takes place under acid or base catalysis or upon heating fig2. Fig.2: Acid or base catalysis upon heating. The formation is generally driven to the completion by separation of the product or removal of water or both. Many Schiff bases can be hydrolyzed back to their aldehydes or ketones and amines by aqueous acid or base. The mechanism of Schiff base formation is another variation on the theme of neucleophilic addition to the carbonyl group. In this case the neucleophile is the amine. In the first part of the mechanism the amine reacts with the aldehyde or ketone to give an unstable addition compound called carbinolamine. The carbinolamine loses water by either acid or base catalyzed pathways. Since the carbinolamine is an alcohol it undergoes acid catalyzed dehydration fig3. Fig.3: Acid catalyzed dehydration Typically the dehydration of the carbinolamine is the rate-determining step of Schiff base formation and that is why the reaction is catalyzed by acids. Yet the acid concentration cannot be too high because amines are basic compounds. If the amine is protonated and becomes non-neucleophilic equilibrium is pulled to the left and carbinolamine formation cannot occur. Therefore many Schiff bases synthesis are best carried out at mildly acidic pH. The dehydration of carbinolamines is also catalyzed by base. This reaction is somewhat analogous to the E2 elimination of alkyl halides except that it is not a concerted reaction. It proceeds in two steps through an anionic intermediate fig4. Fig.4: Addition followed by elimination. The Schiff base formation is really a sequence of two types of reactions i.e. addition followed by elimination 11 . Possible Activities of Schiff Bases: 1 Antimicrobial Activities: Schiff base derived from indoline-2 3-dione and 2-aminobenzoic acid and its Tin complex showed Antibacterial activity against Staphylococcus aureus. The results compared with standard drug Imipinem have indicated that compounds were active but activity was lesser than the standard drug. This activity might be due to the presence of a hydroxyl and phenyl group 21 .The increased activity in the organotin complexes may be due to the coordination and polarity of atin IV atom with oxygen of the ligands. The order of increasing activities is ligands MeSnL PhSnL BZ3SnL the results matched with the previously reported data for the biological activity of organotin complexes 22 . Complexes of CoIICuIINiII MnII and CrIII with Schiff bases derived from 26-diacetylpyridine and 2-pyridinecarboxaldehyde with 4-amino-23- dimethyl-1-phenyl-3-pyrozolin-5-one show antibacterial and antifungal activities against Escherichia coli Staphylococcusaureus Klebsiella pneumoniae Mycobacterium Smegmatis Pseudomonas aeruginosa Enterococcus cloacae Bacillus megaterium and Micrococcus leteus. The results showed that L1 ligand has a greater effect against E. coli than the other bacteria while it has no activity against S. aureus. Metal complexes have a greater effect than L2 against almost all bacteria 23 .The Schiff base 4-chloro-2-2- morphiolinoethylimino methylphenolatomethano lchloro and its ZnIIcomplex were screened for antibacterial activity against two Gram positive bacterial strains B. Subtilis and S. aureus and two Gram-negative bacterial strainsE. coli and P. fluorescence by the MTT method. The Schiff base showed significant activity against two Gram- negative bacterial strains with MIC of 12.5μgmL-1but was inactive against two Gram negative bacterial strains. The Zn complex showed a wide range of bactericidal activities against the Gram positive and Gram negative bacteria were potent than or similar

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Sandeep Rajan et al.: Int. J. Biopharma Research 2013 02 08 163-170 Page | 165 with commercial antibiotics Kanamycin and penicillin 24 . Bidentate complexes of CoIINiII CuII ZnII CdII and HgII with benzofuran-2- carbohydrazide and benzaldehyde BPMC or 34- dimethoxybenzalde hyde BDMePMC showed biological activities. CoII and CdIIcomplexes of BPMC are moderately active toward E.coli whereas CuII ZnII and NiII complexes of BPMC and CuII and ZnII complexes of BDMeOPMC are more active against S. aureaus as compared to free ligands. None of the complexes a reactive against A. niger but in the case of A. fumigatus CuIICoII NiII and CdII complexes of BDMeOPMC are more active than the parent ligands 25 . Amino acid Schiff base derived from 2-hydroxy-5- methylacetophenone and glycine and its transition metal complexes showed bacterial activities. The ligand was bacteriostatic against bacterial strains except Proteus vulgaris Shigella flexneri and Bacillus coagulans. All complexes are either resistant or less sensitive against P. vulgaris. However compared to the antibacterial activity of the standard antibiotics streptomycin the activity exhibited by the ligand and metal complexes was lower. The metal complexes showed to exhibited higher activity than the free ligand against the same organism under identical experimental conditions such increased activity of the metal chelates can be explained on the basis of chelation theory 26 . Antifungal Activities: The microbial activity of the N-2-hydroxy-1 naphthalidene phenylglycine and its transition metal complexes was investigated. From the antifungal screening data it is concluded that the activity of the ligand has increased upon complexation. Cu II NiII and CoII complexes have shown better antifungal activity compared to the ligand and the corresponding metal salts 27 . Two bidentate Schiff base ligands 2-2-hydroxy-3 5-dichloro/dibromo benzaldehyde-4- 3-methyl-3-mesitylcyclobutyl-1 3-thiazol-2-yl hydrazone L1H L2H and their metal complexes were tested against a yeast-like fungus C. albicans 28 . The fungicidal effect of salicylaldimine containing formaldehyde and piperazine moity and its metal polychelates were determind against two yeast Candida albicans and Aspergillus spp. The Cu II-polychelate exhibited high activity against Candida albicans and the other show mild activity. The presence of N and O donor groups in the ligand and its metal polychelates inhibited enzyme production because enzymes that require free hydroxyl group for their activity appear to be especially susceptible to deactivation by the metal ion of polychelates. All the metal polychelates are more toxic than the ligand 29 . Neutral complexes of CoII NiII CuII and ZnII with Schiff bases derived from 3-nitrobenzylidene-4- aminoanttipyrine and anilineL1/p-nitro aniline L2/p-methoxyaniline L3 showed antifungal activity. A comparative study of the MIC values for the ligands and their complexes indicates that the complexes exhibit higher antimicrobial activity. Such increased activity of the complexes can be explained on the basis of overtone’s concept and Tweedy’s chelation theory 30 . Inhibition is enhanced with the introduction of an electron withdrawing nitro group in the phenyl ring 31 . Semicarbazones and thiosemicarbazones complexes of Ni II metal showed antifungal activities against 11 pathogenic fungi. The complexes were moderate active against all pathogenic fungi and much lower than those of standard fungicide Nistatin 32 . CoIINiII and CuII complexes with Schiff base 33’-thiodipropionic acid bis 4-amino-5-ethylimino-23-dimethyl-1-phenyl- 3- pyrazoline showed antifungal activity against Alternaria brassicae Aspergillus niger and Fusarium oxysprum and results indicate that the complexes show the enhanced activity in comparison to free ligand 33 . Anti-cancer and Cytotoxic Activities: Schiff bases are well known for their importance in biological fields 34-39 . Anticancer activities of these compounds have also been studied to some extent. Schiff bases derived from benzoin salicylaldehyde amino phenol with 2 4- dinitrophenyl hydrazine and acetone semicarbazone have shown pronounced anticancer properties. Not only the Schiff bases Schiff base complexes with transition metals have also been investigated for their anticancer activities against Ehrlich ascites carcinoma EAC cells in Swiss albino mice 40-42 . A novel Schiff base complex with copper with potential anticancer mechanism DNA binding cytotoxicity and apoptosis induction activity has appeared very recently 43 . In the present situation we have selected vanillin semicarbazone VSC as a test compound and studied its anticancer activity against EAC cells in vivo. In support of this work haematological studies. Metal complexes of Schiff base derived from 2-thiophenecarboxaldehyde and 2-aminobenzoic acid HL have been recommended and/ or established a new line for search to new antitumor particularly when one knows that many workers studied the possible antitumor action of many synthetic and semi synthetic compounds e.g. Hodnett et al. and Hickman 44 . Such compounds may have a possible antitumor effect since Gram- negative bacteria are considered a quantitative microbiological method testing beneficial and important drugs in both clinical and experimental tumour chemotherapy 45 . A tridentate Schiff base derived from the condensation of benzyldithiocarbazate with salicyldehyde and its Zn Sb Cu complexes showed cytotoxic properties 46 . Copper II complexes containing Schiff bases derived from S-benzyldithiocarbazate and

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Sandeep Rajan et al.: Int. J. Biopharma Research 2013 02 08 163-170 Page | 166 saccharinate showed anticancer properties. The complexes were highly active against the leukemic cell line HL-60 but only Cu NNS sac was found to exhibit strong cytotoxicity against the ovarian cancer cell line Caov-3. The activities being higher than the standard anticancer drug Doxorubicin 47 . Complexes of chromium III are much less cytotoxic than chromium VI to cultured human cells 48 . Chromium III is an essential nutrient that is involved in the glucose tolerance factor GTF in maintenance of normal carbohydrate and lipid metabolism 49 . Synthetic Action on Insecticides: Schiff base derived from sulfane thiadizole and salicylaldehyde or thiophene-2-aldehydes and their complexes show toxicities against insects 50 . α- Aminoacid acts as intermediate in synthesis of photostable pyrthriod insecticides 51 . Flourination on aldehyde part of Schiff base enhances insect acracicidal activity 52 . Schiff bases thiadiazole derivatives with salicylaldehyde or o-vanillin and their metal complexes with Mo II show insecticidal activities against bollworm and promote cell survival rate of mung bean sprouts 53 . Plant Growth Regulator: N-acetylated compounds show growth inhibitory activity with seedling of wheat rye and barley 54 . Schiff bases show remarkable activities on plant hormone such as the auxins on root growth 55 . Schiff base of ester and carboxylic acid show remarkable activity as plant growth hormone 56 . Schiff bases of thiodiazole have good plant growth regulator activity towards auxin and cytokine 57 . Other Therapeutic Activities: Several Schiff bases possess anti– inflammatory allergic inhibitors reducing activity radical scavenging analgesic and anti-oxidative action 58 . Thiazole derived Schiff bases show analgesic and anti-inflammatory activity 59 . Schiff base of chitosan and carboxymethyl-chitosan shows an antioxidant activity such as superoxide and hydroxyl scavenging. Furan semicarbzone metal complexes exhibit significant antihelminthic and analgesic activities 60 . Catalysts: Co II Fe III and RuIII complexes of Schiff bases derived from hydroxy benzaldehyde are used in oxidation of cyclohexane into cyclohexanol and cyclohexanone in presence of hydrogen peroxide. The most efficient catalysts are the FeIII complexes which is unusual because in general the cobaltII complexes have high activity for alkane oxidation reactions 61 . Chromium-salen complexes are well known catalysts both in heterogeneous and homogeneous 62 . Binucleating complexes of Fe Co Ni Zn with Schiff bases neytralbis iminopyridyl benzene and monoanionic bis iminopyridyl phenolate acts as catalysts in the oligomerisation of ethylene 63 . New manganese II and manganese III complexes of substituted N N’- bis salicylidine-1 2-diimino-2-methylene appear to be efficient models for peroxidase activity 64 . New CopperII complexes of indoxyl thiosemicarbazone ITSC show one pair of well defined reduction peaks at different potential in the forward scan which represent the reduction of Cu++ to Cu+ by one electron process and subsequent oxidation of Cu+. The quasi reversible nature of the Cu++/Cu+ is due to inherent reducing tendency of thiosemicarbazone ligands 65 . Ruthenium and cobalt complexes with Schiff bases bis salicylaldehyde-o-phenylene-diaiminesaloph and substituted ClBr and NO2 oxidize α-pinene into camphene 277-trimethyl ss pinene 3- oxatricyclo- 411o24-octane 23-epoxy campholene aldehyde and D-verbenone 66 . Ni II complexes with bidentate NN ligands become an efficient catalyst precursor for olefin oligomerisation in presence of an activator 67 . A wide variety of cobaltII complexes are known to bind dioxygen more or less reversibly and are therefore frequently studied as model compounds for natural oxygen carrier and for their use in O2 storage as well as in organic syntheses due to their catalytic properties under mild conditions 68 . Antifertility and Enzymatic Activity: About 20 Zinc enzymes are known in which Zinc is generally tetrahedrally four coordinate and bonded to hard donor atoms such as nitrogen or oxygen 69 . The Schiff base complexes of 2- pyridinecarboxaldehyde and its derivatives have been reported to posses high super oxide dismutase activities 70 . Recently the interaction of DNA with complexes Cr Schiff base OH22 ClO4 was reported 71 . Ternary complexes of Cu II containing NSO donor Schiff base showed DNA cleavage activity. In the presence of 3-Mercaptopropionic acid 5mM as a reducing agent the complexes 40 μM show efficient DNA cleavage activity giving the order NSO-dppz ONO-dppz NSO-dpq ONO dpq 72 . Dyes: Chromium azomethine complexes cobalt complex Schiff base 73 unsymmetrical complex 1:2 Chromium dyes give fast colours to leathers food packages wools etc 74 . Azo groups containing metal complexes are used for dying cellulose polyester textiles 75 . Some metal complexes are used to mass dye polyfibers 76 . Cobalt complex of a Schiff base salicylaldehyde with diamine has excellent light resistance and storage ability and does not degrade even in acidic gases CO2 77 . Novel tetradentate Schiff base acts as a chromogenic reagent for determination of Ni in some natural food samples 78 .

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Sandeep Rajan et al.: Int. J. Biopharma Research 2013 02 08 163-170 Page | 167 Polymer: Photochemical degradation of natural rubber yield amine terminated liquid natural rubber ATNR when carried out in solution in presence of ethylenediamine 79 . ATNR on reaction with glyoxal yield poly Schiff base which improves aging resistance. Organocobalt complexes with tridentate Schiff base act as initiator of emulsion polymerization and co-polymerization of dienyl and vinyl Monomers 80 . Miscellaneous Applications Transition metal complexes with 1 10- phenanthroline and 2 2-bipyridine are used in petroleum refining 81 . Popova and Berova reported that copper is good for liver function its level in blood and urine has influence in pregnancy disorders nephritis hepatitis leprosy anemia and leukemia in children 82 . NLO Metal complexes of Schiff base derived from tetradentate precursor 1- phenylbutane-1 3-dionemono S- methylisothiosemicarbazone with o-hydroxy benzaldehyde or its phenylazo derivative showed nonlinear optical NLO properties. A comparison between complexes of different metals with the same phenylazo-substituted ligand indicated that the NLO response strongly depends upon the electronic configuration of the metal center 83 . It has been reported that Zinc II complexes with Schiff bases type chelating ligands can be used as an effective emitting layer 84 . In addition it has also been shown that Zinc II complexes with benzothiazoles which are oxidized forms of benzothiazolines are luminescent 85 . Zinc II and Cadmium II complexes with N2S2 -Schiff base ligands are a new class of luminescent compounds and the careful derivatization of the substituent’s on the pendent phenyl rings permits a fine tuning of the emission wavelength 86 . Baker’s yeast contains a benzofuran derivative which acts as an antioxidant preventing haemorrhagine liver necrosis in rats and haemolysis of red cells in vitamin E deficiency 87 . Amino acid Schiff base complexes derived from 2-hydroxy-1- naphthaldehydes are important due to their use as radiotracers in nuclear medicine 88 . Macrocyclic Schiff bases of Dithiocarbazic acid have many fundamental biological functions such as photosynthesis and transport of oxygen in mammalian and other respiratory system 89 . Chemistry of vision The chemistry of vision makes use of an imine linkage between the aldehyde derived from vitamin A and the opsin protein situated in the retina of eye. The chemical changes in the cell take place with the help of larder proteins which catalyze the changes and vitamins play their role as coenzymes i.e. they are assisting the functioning of many enzymes. The most important example in this regard is the active form of the vitamin B6 which is pyridoxal phosphate in actual sense. The most important feature to be considered is that amino acid groups in the enzymes make an imine with the aldehydic groups in vitamin B6. The transfer of the amino group from one amino acid to another i.e. transamination is actually catalyzed by the coenzymes which are bound to enzymes and possesses significant importance in the biosynthesis of amino acids. The imine to pyridoxal and the modified amino acid linkage is cleaved by the enzyme-catalyzed hydrolysis in the last step. As electroluminescent materials in non-linear optical devices In electrochemical sensors Synthetic action on insecticides polymer corrosion inhibitor. Conclusion The above mentioned are some of the activities applications of Schiff bases and its derivatives. There are still more applications of Schiff’s bases are hidden inside. This review outlined to have a sufficient knowledge Schiff base and its applications. Along with that to remind us to reveal the hidden mysteries of Schiff bases and a lot more applications and uses and benefits are still hidden in Schiff base and its derivatives. This review suggested to pharmacists medical professionals professors researchers scholars and scientists that there is a need to excavate the new pharmacological activities to make the people a better living. References 1. P. A. Vigato and S.Tamburini Coord.Chem. 2004 Rev. 248 1717. 2. B. S. Bahl and A BahlElementary Organic Chemistry Schand and Company Ltd. New Delhi 1993 p. 60. 3. C.T.Barboiu M. Luca C. Pop E. Brewster and E. M. Dinculescu Eur. J. Med. Chem. 1996 31 597. 4. J. M.Gemi C. Biles J. B.Keiser S. M. Poppe S. M. Swaney W. G. Tarapley D. L. Romeso and Y. Yage J.. Med. Chem. 2004 43 1034. 5. H. Keypour M. Rezaeivala L.Valencia P.Perez Lourido and H. Raza Khavasi Polyhedron 2009 28 3755. 6. K. S. Suslick and T.J.Reinert J. Chem. Educ 1986 62 974. 7. J. Tisato F. Refosco and F. Bandoli Coord. Chem. Rev. 1994135 325. 8. Carey FA Sundberg RA. Advanced Organic Chemistry. 5th ed. New York: Springer2007. 9. Chhonker YS Veenu B Hasim SR Kausik N Kumar D Kumar P. Synthesis and pharmacological evaluation of some new 2-phenyl benzimidazoles derivatives and their Schiff’s bases. E-J Chem. 2009 6S1:S342- S346.

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