05 Chapter 2
05 Chapter 2
Science Finder search includes search of the Chemical Abstracts (CA), Chemical Abstracts Plus(CA PLUS) and MEDLINE.The search was done using the key word, Schiff Bases.The outcome of the survey is presented below.
Hann, Raymond, M. et al., (1929) prepared Schiff bases from 5-chlorovanillin1. The 5-chlorovanillal derivatives were prepared by heating the aldehyde with amine in 95% ethanol.o-toluidine, p-toluidine, m-nitroaniline, p-chloroaniline, cymidine, panisidine, benzidine, m-aminobenzoicacid, p-aminophenol, o-dianisidine bis-nitro-ptoluidine Schiff bases were synthesized. No derivatives could be obtained from ortho & para nitroaniline, 2, 4-dichoroaniline and trinitroaniline.
Vavon . G and Montheard P. (1940) have described the formation of Schiff bases from methylamine, p and o-HOC6H4CHO, p and o-MeOC6H4CHO, o-vanillin and vanillin in the solvents PhCH2OH, EtOH, dioxane, PhNO2, MePh (and 3% alc.) and CHCl3.2
Woelm, Firma M (1941) prepared Schiff bases from o-vanillin and sulphanilamide by reacting them in the cold by themselves or in the presence of solvents to obtain a red product which on heating changed to a yellow isomer. The o-vanillin sulfanilamide derivative was found to possess therapeutic properties.3
Lespagnol, A. et al., (1945) prepared the Schiff base Ph2CHN:CHPh from Benzhydrylamine carbonate.Similarly Schiff bases from anisaldehyde, piperonal and vanillin were synthesized.4 The Schiff bases were reduced by sodium in absolute ethanol and product neutralised with alcholic Hydrochloric acid to give N-
benzylbenzhydrylamine-HCl, p-methoxybenzyl analog, 3, 4-methylenedioxybenzyl analog, and the 4- hydroxy - 3 methoxy benzyl analog did not exhibit local anesthetic action but the other 3 analogs have shown same activity as Ph2CHNH2.The pmethoxybenzyl analog exhibited strong antispasmodic activity, active at a dilution of 1:200,000 on isolated rabbit intestine.
Wells, F.V. (1948) has described the preparation of Schiff bases of methylanthranilate and aldehydes or Ketones namely hydroxycitronellal, anisaldehyde (acaciol), cumaldehyde, cinnamaldehyde, amylcinnamaldehyde, citral, vanillin, ionone, musk ketone, methyl napththyl ketone and acetophenone by gently heating at 65c ,one mole equivalent. Benzaldehyde, phenyl acetaldehyde, salicylaldehyde and
methylacetophenone yielded compounds, which were of little interest. Some of the hydroxy citronellal derivatives yielded products with floral notes.5
series of
Schiff bases
from aminonucleoside. These compounds were evaluated for anti-amoebic activity. Only the vanillin and ethyl vanillin derivatives showed any activity.6
Bose, A., (1957) has described the preparation of Schiff bases of isoniazid by condensing it with molar proportions of anisaldehyde, cinnamaldehyde, veratraldehyde and vanillin in the presence of dilute ethanol.7
Balog, I., et al., (1961) have prepared Schiff bases using aldehydes like o-vanillin and salicylaldehyde with aromatic amines, in order to prepare chelates of iron III with these Schiff bases.8
bases by reaction of
salicylaldehyde (I) with p-octyl-o-aminophenol(II), o-vanillin with (II),p-sec-decyl-oaminophenol with o-hydroxyacetophenone , 2-hydroxy - 4 methoxybenzophenone
with p- pentoxy-o-aminophenol, and (I) with o-aminophenol .These Schiff bases were prepared to synthesise transition metal chelates for their potential as stabilizers for gasoline and polymers.9
Balog, J. et al., (1965) applied Schiff bases of o- phenylenediamine and vanillin (I),resorcylaldehyde (II) , resacetaophenone (III) to oat seeds and to capsicum seeds to determine the effect of Schiff bases on germination. In the case of the oat seeds compounds I, II and IV showed better germination and subsequent development. III showed better germination but subsequent development was poor. With capsicum seeds II, III &IV caused an increase in germination when applied at the rate of 1, 2, and 4mg. /100 seed.10
Sato, Hirouki et al., (1973) have prepared new Schiff base derivatives of antibiotics such as colistin, kanamycin, polymyxin, gentamycin, and neomycin which
contain at least one amino group .The aldehydes that used for the synthesis were 2,3 (OH)(COOH)C6H3CHO , 3,4-(COOH)(OH(C6H3CHO, PhCHO, o -Vanillin, 2,53,4-
(salicylaldehyde, o-vanillin and isovanillin and aniline derivatives) with acid.Their UV, Visible and IR spectral behaviour was investigated.The charge
Singh, Ajit. et al., (1975) prepared Schiff bases by the reaction of vanillin with RC6 H4 NH2 (R = H, p-Me, p-MeO, pEtO, p-OH, p-halo, m, or p-NO2). Water formed during the reaction was removed by azeotropic distillation or by use of anhydrous ZnCl2. The NaBH4 reduction of the products to secondary amines was restricted sterically in the case of p-Me derivative.13
Witzke,N.M. (1976) have prepared Schiff bases of Colistin and Polimyxin B using 3,4 - R1R2C6H3CHO (R1=H, R2=H, OH, NMe2 ; R1= OMe , R2=OH) to give
benzylidene derivatives.These Schiff bases were reduced using NaBH4 .The antibacterial derivatives were screened for activity against Staphylococcus aureus and
Escherichia coli.The inceased lipophilicity of polymyxins substituted with benzyl groups increased the activity against S.aureus and reduced the activity against E.coli.14
Goghari,M. et al., (1977) prepared bactericidals I (R = Ph, 4-MeOC6H4, cinnamyl, 3- OHC6H4, 4-OHC6H4, 3-NO2C6H4, 4-NO2C6H4, vanillyl, 2-furyl, Me) by cyclocondensation of HSCH2COOH with prepared Schiff bases II .I were characterized by spectra, the S, S-dioxides, and benzal derivatives III.II were more effective bactericides than were I.15
Biradar, N.S.et al., (1977) have prepared Schiff base from salicyaldehyde
and
Joshi, Puran Chandra., et al.,(1978) prepared new 2,4-dinitrophenyl and 2,4,6trinitro phenyl ethers of vanillin Schiff bases (I and II; R=H, Cl Br, I, Me, OMe, NO2) and screened for their fungicidal activity against Alternaria alternata, Drechslera papendorfii and Helminthosporium oryzae. I was somewhat more effective than II.17
Lambrou, Demetrios. (1979) condensed 2, 3-RO (R1O) C6 H3 CHO (R= R1 = Me, PhCH2; R1 = Me, R=Et, Pr, Bu, PhCH2) with isoniazid or thiosemicarbazide, which gave a yield of 86 99% (I) and 68-93% (II). They were found to be potential fungistatic and tuberculostatic agents. 1-HCl was also obtained.18
Mazumdar, A. K.D., et al., (1979) prepared Schiff bases I and II by refluxing elthanolic solutions of aldehydes with the respect thiazoleamines. The yield was 60-76%. l(R1 = HOOC CH2 CH2 R = eg., P-NMe2, m-OH, p-NO2, o-NO2, o-Cl, H, p-
OH; R1 = H, R = p-Me2, N; R1 = Me, R = H, p-NMe2) and ll(R2 = SCN R = eg. H, o-Cl, p-OH, p-O2N, o-O2N, m-OH; R2= H R= p-Me2N) 19.
Drugarin, C., et al., (1981) have synthesized Schiff bases using hippuric acid. Schiff bases (R=H , 2-, 4-OH , 4-MeO , 4-NO2 , 4-AcNH , 4-Me2N and 4-
4-NH2C6H4CONHCH2COOH
Tewari, S. S., et al., (1981) prepared Anilinobenzylidenes I and II (R=Cl, Me, MeO, EtO; R1 = 3-Cl, 4-Cl, 4-Me, H; R2= Ph, 4-Me C6 H4, 3-MeC6H4, 4-EtO C6H4) from 4-RC6H4 (O Me) OH-3,4. I (R=Cl, Me, EtO, MeO; R1=3Cl, 4-Cl) and II (R=Cl, EtO; R2=4-MeC6 H4, 4-Cl C6 H4, 4-EtO C6 H4) showed no anticonvulsant activity.21
soluble co - polymers of these Schiff bases with N- vinyl - 2 - pyrrolidone and N, Ndimethylacrylamide was obtained. The hydrolytic behaviour of the Schiff base monomers
and co -polymers to liberate perfume aldehydes was structure dependent, thereby affording chemical release control.22
Thakur, A.B., et al., (1982) identified a violet coloured compound formed from the TLC of polythiazide I using acidified vanillin (II) spray reagent as III. At pH9 I partially decomposed to IV which reacts with Me 2 CO to form V. V hydrolysis and the Me2CO released reacts with IV to violet coloured spot in chromatograms. II is used as flavouring agent in tablets.23
Rai, Mangat, et al., (1982) have prepared twelve Schiff bases by condensing equimolar quantities of veratraldehydes and anilines in PhMe. They were reduced with NaBH4.Schiff Bases with electron donating substituents in the N-Ph ring showed remarkable activity against the fungi Alternaria solani and Colletotrichum capsici.24
Kumar,
Surinder.,
et
al.,(1982)
showed
that
BrCN
adds
to
p-
hydroxybenzalanilines and vanillin Schiff bases to give 3,4-R(OH) C6 H4 CH(CN) NBr C6 H4, R1 p(R=H, MeO; R1=H, Me, OMe, Cl).25
Dash, B., et al., (1983) have synthesized Schiff bases from vanillin as possible fungicides. Schiff bases I (R, R1=H, Ph, 4-MeC6H4, 4-BrC6H4, 4-MeOC6H4 , 4- ClC6H4 , naphthyl, R=H) derived from 4 -substituted and 4,5-disubstituted-2- Aminothiazoles were prepared.Cycloaddition of I with SHCH2COOH yielded thiazolidones reaction with
piperidine and morpholine yielded corresponding derivatives. The compounds were screened for their fungicidal activity.26
Ghose, B.N. (1983) prepared six Schiff bases by the condensation of C6H5COCOC6H5 with HOCH2CH2NH2(I) and H2NCH2CH2NH2(II),
CH3COC(=NOH)Me: NOH and 9,10-phenanthrenequinone with I and 2,3-(OH)(MeO) C6H3CHO with II and (H2NCH2)2 CH OH.27
Ghose, Bhupendra.N. (1984) prepared five new Schiff bases as potential ligands having the ONNO donor system. PhCOCOPh (I), MeCOCMe:NOH and 9,10-
phenanthrene quinone were condensed with H2N CH2 CH2 OH and 2,3(OH)(MeO)C6H3CHO was condensed with HOCH(CH2NH2)2 and (H2NCH2)2 (II).
Csaszar, J. et. al., (1987) studied the UV, visible and IR spectra of the Schiff bases formed from salicylaldehyde, o-vanillin with aniline and substituted anilines. At 400-450 nm an intense band indicative of the benzenoid-quininoid tautomer equilibrium was observed. Correlations were found between the intensities of these bands, the
Na, Chongwu, et al., (1988) obtained Schiff bases by the reaction of o-vanillin with ethylene diamine, benzidine, o-phenylene diamine, m-phenylene diamine in ethanol
or benzene. Through the reaction of o-vanillin with 1, 8-diamino naphthalene under similar reaction conditions gave a cyclic compound.30
Goudar, T.R. et al., (1988) have synthesized Tin (IV) complexes from Schiff bases derived from salicylaldehyde, o-vanillin & 2-aminopyridine, 2-amino-3methylpyridine and 2-aminothiazole. The complexes were non-electrolytes and ligandmetal linkage through the phenolic OH and the azomethine N.31
Chatterjee, Papia et al., (1989) prepared six Schiff bases viz., vanillin semicarbazone, 2- furfuraldehyde semicarbazone, 2-furfuraldehydethiosemicarbazone, salicylidene-2-aminopyridine and 2-hydroxy-1-naphthylmethyl-2-aminopyridine. Their metal complexes with biphosphorous cations were also synthesized.32
Skwarski, et al., (1989) prepared Schiff bases by the reaction of 2-hydroxy benzaldehyde, 3-methoxy 4-hydroxy benzaldehyde & 3-methoxy-4-benzyloxy benzaldehyde with N-sulfanilyl - 6-methyl - 2 - aminopyridine, N-sulfanilyl-4,5-dimethyl - 2-aminooxazole, N-sulfanilyl - 3-methoxy - 2-aminopyrazine, N-sulfanilyl 5 methoxy 2 - amino pyrimidine and N-sulfanilyl- 6 - methoxy 3 -amino pyridazine. The compounds were found to have cholagogic and choleretic activity.33
Cardile V, et al., (1989) synthesized a series of Schiff bases combining thiazolyl and benzothiazolyl ring and vanillin moieties in same molecule and evaluated for screening anti-degenarative activity on nasal pig cartilage cultures treated with
interleukin 1 beta, (IL-1 beta). The amount of glycosaminoglycans (GAGS), the production of nitric oxide NO and PGE2 (prostaglandins), released into the cultured medium were detected.34 The Schiff base produced decreased with dose the NO and PGE2 production and GAG's release with samples treated with IL-Ibeta. Hence thiazoloyl and benzothiozolyl Schiff bases and Schiff bases with bromine and methoxy group in third position was found to protect cartilage matrix from degenerative factors induced by IL Ibeta.
Chatterjee, Papia, et al., (1990) synthesized Schiff bases (HL), by the condensation of vanillin or 2-furfuraldehyde and 4-phenylthiosemicarbazide. The Schiff bases when reacted with transition metal salts gave ML2.2H2O (M = Co, Ni Cu Zn, Cd). M is coordinated via azomethine N and thiolo S atoms. Structures were proposed for the new octahedral complex on the basis of various analytical methods. The calculated ligand parameters were found to be consistent with the proposed geometry.35
by the reaction of 5-
formylvanillin, with aromatic amines like 1 or 2 naphthylamine, aminopyridine and (un)substituted anilines. The yield was usually more than 80%.36
Geronikaki,A. (1990) condensed 2 aminothiazoles (R=,4-Ph) with 3 , 5 , 4 R1R2(OH)CH2CHO (R1=H,I,R2=Ome;R1=R2=H )to give a series of Schiff bases.37
Kayahara, Hiroshi. et al., (1991) prepared several Schiff bases (I) of perillaldehyde, benzaldehyde, cumin aldehyde and vanillin with aniline, hydroxyaniline and D-glucosamine and N-acylated amino acid derivatives (II) using serine, theronine
and organic acids such as perillic acid, camminic acid, phenylacetic acid, vanillic acid, trans-cinnamic acid and ferulic acid. (l) had no taste, most (ll) with the C- terminus protected had a bitter taste and those with the C-terminus unprotected had a sour taste.38
Zhou, Jian-Feng et al., (1998) have synthesized new Schiff bases by refluxing paminophenylthioaceticacid by with RCHO(R= substituted Ph) in ethanol.39
Golovanov, A.S. et al., (1998) have synthesized the novel mesomorphic Schiff base 2 - (4-Alkoxybenzylidenamino) 4 - [(4-nitrophenyl) amino] thiazoles.40
Oza, Haresh. et al.,(1998) have synthesized thirty novel thiazolidinone (1) derivatives as potential anti-tubercular agents.R=Ph,ClC6H4, 4-Me2NC6H4,
NO2C6H4,PhCH:CH , etc,;R1=H,Me) by cyclocondensation with thioglycollic acid and thiolactic acid. The compounds were screened for their anti-tubercular activity against Mycobacterium tuberculosis.41
Zhou Yiming, et al., (1999) have synthesised a number of Schiff bases in the absence of solvents. The process consisted of mixing aromatic aldehydes like o, p, & m nitrobenzaldehyde, p - dimethylaminobenzaldehyde , o,m & p-hydroxybenzaldehyde and p- methoxybenzaldehyde with amines like aniline, p-chloroaniline, p- methylaniline, p-
phenylenediamine, semicarbazide HCl, 4-aminoantipyrin.Acids like H2SO4,HCl, H3PO4,Carboxylic acids, phenolic acids , sulphonic acids were used in trace quantities as acid catalysts.42
Rathod, Amarsingh et al., (2000) have synthesized Schiff bases by condensing 2amino - 4 phenylthiazole , 2 - amino - 4 - methylbenzothiazole, 2 amino - 6 methylbenzothiazole and 2 aminobenzothiazole with differently substituted
benzaldehyde and 2- furfuraldehyde.The new compounds showed antibacterial activity against gram positive and gram negative organisms.43
new Schiff
bases
containing Et1H-1,2,4 -triazole-3 - carboxylate by the reaction of Et 5-amino triazole - 3 - carboxylates with substituted benzaldehydes.44
Vishwanathmurthi.P.et al., (2000) have synthesized Schiff bases by condensation of o-vanillin with aniline, o-toluidine or p-toluidine in benzene in the presence of
NEt3.These Schiff bases were used to synthesise ruthenium complexes.The Schiff bases and the complexes were tested in vitro against the pathogenic fungi Aspergillus niger and Fusarium Sp.45
Wang Guangbin et al., (2000) synthesized a new dipeptide by the condensation of DL- alanyl-DL-alanine with o-vanillin .The copper, zinc, nickel and cobalt comolexes were prepared and characterized.46
Gong, Qiao-Juan et al., (2000) have prepared five Schiff bases using substituted benzaldehyde and 4 -amino antipyrine. It was found that the fluorescence intensities of the compounds at optimum aminoantipyrine.47 pH values were 16 to 319 times as much as that of
Wu, Gen, et al., (2000) reacted chitosan with vanillin aldehyde by a Schiff base reaction in water. The graft percentage was related with reacting time, reacting temperature and monomer concentration.48
Varbanov, S.et al., (2000) have prepared a group of Schiff bases from aminomethyldimethylphosphine oxide with aromatic aldehydes.49
Xie,Yuli. et al., (2000) have synthesized phenol substituted bisphosphonate RC6H4CH:N-3(4)-C6H4NHCH(PO (OCH3)2)2 (R = 3,4-(OH)2 , 2,3 OCH3 4-OH,-2, 3 OCH3-4-OH,3-OCH3-4-OAc,2-OH,3,4-(OCH3)2,2-OH-3-OCH3, 3,4 CH2O2), from
nitroaniline and substituted benzaldehyde by reduction and condensation reaction and their antitumour activities on P338 cells and A-549 cells in vitro were tested.The position of the phenol hydroxyl group in the synthetic compounds showed important effect on the antitumor activity. The synthetic compounds, in which the phenolic hydroxyl group was next to the double bond of the Schiff bases was found to be more effective than others.50
Sun, Ming, et al., (2001) have synthesized four new Schiff bases from o-vanillin and dl- amino acids. The conformations of the four Schiff bases have been studied using molecular dynamics and quantum chemical analytical approaches.51
reaction of 2-amino-1-benzylamine and 3-methoxysalicylaldehyde in ethanol. The molecular structure of (I) was confirmed by single crystal X-ray crystallography.52
Kam, Li., et al., (2001) have synthesized 1:1 and 1:2 Schiff bases derived from 2, 3-diaminopyridine (DAPY) and o-vanillin and eight transition metal complexes of these Schiff bases. The Schiff bases and most of the metal complexes displayed antibacterial activity.53
Shakih Kabeer, A., et al., (2001) have synthesized Schiff bases using Benzothiazole with a substitution X-R in the second position. Derivatives where [ X = N:C (Me), NHN:C(Me), N:CH, NHN:CH, R=C6H4;2-OH, C6H3.2,5(OH)2, C6H3 2OH4-Cl, C6H3-2,4-(OH)2, 2-pyridyl] were synthesized and tested for their antibacterial and antifungal activity.54
Jayabalakrishnan, C. et al., (2001) have prepared Schiff bases by condensing salicylaldehyde , o-vanillin or o-hydroxyacetophenone with N(4)-
ruthenium complexes.These complexes were tested for in-vitro growth inhibitory activity against Pseudomonas sp.,Bacillus sp.and Eschereria coli.55
Mohan, S.; Saravanan, J., (2002) have synthesized Schiff bases by treating 2 amino-3-(N-o- tolylcarboxamido)-4,5dimethylthiophene with arylaldehydes. Some of the Schiff bases exhibited antibacterial activity that was less than that of ampicillin.56
Mohan, S. and Saravanan, J., (2002) have synthesized thirty new Schiff bases by treating 2-amino-3- (N-tolylcarboxamido) - 4,5 trimethylenethiophenes with ten
different substituted aromatic aldehydes.Some of the bases have exhibited antibacterial activity.57
Khan, Suroor A., et al., (2002) have synthesized Schiff bases of Isoniazid and evaluated them for their anti-bacterial activity using Staphylococcus aureus as test organism. The zone of inhibition was compared with standard amikacin.58
Sleema, B., et al., (2002) have synthesized Schiff bases by refluxing o-vanillin with L-histidine. These compounds were synthesized to prepare iron, nickel and copper complexes for the X-ray diffraction studies.59
Khan, Suroor A., et al. (2002) have synthesized Schiff bases of Isatin.These compounds were evaluated them for analgesic activity. The Schiff bases were found to possess analgesic activity comparatively less than aspirin.60
Jayabalakrishnan, Chinnaswamy, et al., (2002) have prepared Schiff bases by condensing salicylaldehyde or o-vanillin with o- aminophenol and o- aminothiophenol in their effort to obtain different ruthenium complexes.61
Singh, Gurmit, et al., (2002) have prepared Schiff bases by condensation from 4amino-3-mercapto-6-methyl-5-oxo-1, 2 ,4-triazine with anisaldehyde, o- vanillin,indole3-carboxaldehyde and acetophenone. These bases were prepared as part of their effort to synthesise new complexes of cobalt, nickel, copper and zinc.62
Wang, Yan-Gang et al., (2002) synthesized twelve new Schiff bases containing the 5-amino-1H-1, 2, 3,4-tetrazolyl moiety. These Schiff bases were converted into alpha - (5 - tetrazolyl) aminoalkylphosphonates by treatment with (Et O) 2P (O) H.results of the biological tests show that some of these compounds have remarkable plant growth regulating activity. The Schiff bases derived from chlorobenzaldehyde and 3formylindole were the most active.63 Ren,Shijun et al., (2002) have synthesized thirty new Schiff bases of hydroxy semicarbazide , ArCH:NNHCONHOH (Ar=CF3C6H4, 3-Pyridyl , 5-nitro-2-
thienyl,etc.,) and tested against L1210 murine leukemia cells . Quantitative Structure Activity Relationship (QSAR) analysis showed that beside the essential pharmacophore (NHCONHOH), hydrophobicity, molecular size/polarizability and the presence of oxygen containing group at the ortho position were found to be important determinants of antitumor activity.64
Mohan, S., Saravanan, J., (2003) have synthesized thirty new Schiff bases by treating 2-amino-3-(N-tolylcarboxamido)-4, 5-pentamethylene thiophenes with 10 different substituted aromatic aldehydes.Some of the bases have exhibited antibacterial activity.65
Zakrzewski, Andrzej, et al., (2003) have synthesized a series of substituted Nbenzylidene - 4 - (4,5 - diphenyl -1H-imidazol-2- yl) anilines and investigated the fungicidal activity against 6 microorganisms.66 Qiao,Yanhong, et al., (2003) have studied the inhibitory activity of o-vanillin Schiff base of amino acids and their complexes on the formation of O2-. It has been reported that the Schiff base and their complexes may inhibit O2-.67
Singh, P.H.Ashutosh et al., (2003) have synthesized new Schiff bases derived by nucleophilic addition of p-nitrobenzaldehyde,2pyridinecarboxaldehyde,o-
nitrobenzaldehyde and o-vanillin to 4-amino-5-mercapto-3-metyyl-s-triazole and 4amino-3-ethyl-5-mercapto-s-triazole.Bivalent metal complexes of Co,Ni,Cu,Zn were prepared using these Schiff bases.68
synthesized
three
new
series
of
benzo[d]isothiazole and thiazole Schiff bases and evaluated for antiviral and drug resistant cancers ( leukemia, carcinoma, melanoma ,MDR tumors) for which no definitive cure is available at present .The benzo [d] isothiazole compounds showed marked
cytotoxicity against the human CD4+ Lymphocytes (MT-4) that were used to support the HIV-1growth.The results also showed that the benzo[d]isothiazole derivatives inhibited the growth of leukemia cell lines and one compound showed anti-proliferative activity against two solid tumor derived cell lines.69 Geronikaki, Athina.et al., (2003) have designed, synthesized and identified several new thiazolyl / thiazolinyl / benzothiazolyl Schiff bases .The compounds have been reported to act as lipoxygenase inhibitors affecting inflammation and or psoriasis. The compounds were screened for their reducing activity (with the stable free radical 1, 1-diphenyl- 2 picryl hydrazyl, DPPH) and for inhibition of soybean lipoxygenase
(LOX). Anti-inflammatory activity was examined invivo using the paw oedema method.70
Zhu, Xin-de et al., (2003) have prepared Schiff bases of 2-amino-5-mercapto-1, 3, 4-thiadiazole with salicylaldehyde or o-vanillin and their molybdenum complexes. Their effect on promoting cell survival rate of mung bean sprouts has been investigated.71
Shetty et al., (2004) have synthesized and evaluated the antibacterial activity of thirty Schiff bases synthesized from 2-amino-3-(N-chlorophenyl carboxamido)-4.5this compound
with ten different aldehydes.(R=XC6H4,=2-Cl, 4-Cl, 2-OH, 2-NO2, 3- NO2, 4-Me, 4MeO, 4-Me2N, 3,4-(MeO)2-C6H3, 3,4,5-(MeO)3C6H2.72
Venugopal,K.N.,
et
al.,
(2004)
have
synthesized
Schiff
bases
of
aminothiazolylbromocoumarin by treating 2-amino-4-(6-bromo-3-coumarinyl)thiazole with substituted aromatic aldehydes.The compounds were evaluated for analgesic and anti-inflammatory activity.Some of the compounds have shown interesting biological activity based on the presence of certain functional groups.73
Vaghasiya,Yogesh Kumar et al., (2004) have synthesized some Schiff bases using vanillin with 2,4- dimethylaniline and sulphamethoxazoles as the side chain in DMSO and their antibacterial activity was studied against some gram positive and gram negative strains.These compounds were found to exhibit promising antibacterial effects.74
Jayashree, et al., (2004) have synthesized new Schiff bases by treating 2 - amino 4 - (3- coumarinyl) thiazole with different aldehydes. Several of these Schiff bases exhibited analgesic and anti-inflammatory activity.75
Naik, Bhanvesh, D., et al., (2004) have synthesized some heterocyclic Schiff bases by treating 2-amino 4- (couraminyl-3) thiazole with different aldehydes and
then treating thecompounds with chloroacetylchloride.The compounds were screened for their antibacterial activity.76
Wang, Jian et al., (2004) have synthesized novel Schiff base molecular tweezers under microwave irradiation. The reaction time was brought down from 5 hours to 12-15
minutes, in comparison to conventional heating but also with improved yield. The compounds were characterized by IR, MS and Proton NMR spectra.77
Xia Min et al., (2004) have prepared Bis (indolyl) methane derivatives in good yields under solvent free microwave irradiation, through lewis acid catalyzed elecrophillic substitution of indoles with aldehydes and Schiff bases of aryl aldehydes.78
Babu, K.Sudhakar et al., (2004) have reported the synthesis and characterization of a new Schiff base orthovanillin-Tris (hydroxymethyl) methylamine. They have carried out detailed polarographic study as a complexing agent in the presence of lead ions.79
Tang, Li-jun et al., (2004) have reported the synthesis of flavones containing a Schiff base moiety.80
Xu, Tao et al., (2004) have synthesized a novel Schiff base compound by the reaction of o-vanillin and hydroxylamine hydrochloride in absolute methanol.81
Paneerselvam et al.,(2005) have synthesized a series of Schiff bases of 4 - (4amino phenyl) morpholine (R=(un)substituted Ph,CH:CHPh,2-furyl) and screened them for antibacterial and antifungal activities. All the compounds exhibited antibacterial and antifungal activities.82
From the literature survey the following conclusions could be made: 1) The synthesized Schiff Bases have been mainly evaluated for different biological activities .They have been intensely probed for among other activities for their analgesic , anti-inflammatory
70,73,75
, antimicrobial
& antioxidant70
activity.Good antimicrobial and antioxidant activity have been reported. 2) Small molecules bearing the pharmacophores like phenolic hydroxyl groups, hydrazide, semicarbazide, thiosemicarbazide or the carbon double bonded nitrogen functional groups as in the Schiff bases possess the potential to act as effective antiinfective agents. 3) Schiff bases synthesized by reacting aldehydes like salicylaldehde, vanillin, anisaldehyde, paradimethylamino benzaldehyde, benzaldehyde etc., with a various aromatic amines hold the exciting possibilities of relatively small molecules possessing good antiinfective properties devoid of adverse effects. 4) As antioxidant ativity has been linked to Schiff bases, it would be worthwhile to explore the antioxidant property of the Schiff bases. 5) Time and labour saving efficient methods of synthesis like combinatorial synthesis offers excellent prospects for rapid synthesis of hundreds of compounds. 6) Very cost effective environment friendly method of synthesis applying green chemistry like use of microwave irradiation has been successfully applied to the synthesis of compounds like Schiff bases.
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