Synthesis and Antimicrobial activity of some new

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Synthesis and Antimicrobial activity of some new Schiff bases

This content has been downloaded from IOPscience. Please scroll down to see the full text. 2013 J. Phys.: Conf. Ser. 423 012006 (http://iopscience.iop.org/1742-6596/423/1/012006) View the table of contents for this issue, or go to the journal homepage for more

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ScieTech 2013 Journal of Physics: Conference Series 423 (2013) 012006

IOP Publishing doi:10.1088/1742-6596/423/1/012006

Synthesis and Antimicrobial activity of some new Schiff bases Karamunge K G1, Vibhute Y B2 1

Department of Chemistry, Baliram Patil College, Kinwat-431804 (MS) India 2 P. G. Department of Chemistry, Yeshwant College, Nanded-431 605 (MS) India. E-mail: [email protected] Abstract New Schiff bases derived from 4iodoaniline, 4-chloroniline, p- toluidine and halogenohydroxy substituted acetophenone have been synthesized. All the compounds have been characterized by IR, H1NMR and mass spectral, halogen, nitrogen analysis. The synthesized compounds have been screened for antimicrobial activity.

Keywords: Synthesis, halogenohydroxy acetophenone, Schiff bases, antibacterial, antifungal activity 1. Introduction Compound containing an azomethine group (-CH = N) are known as Schiff bases. Schiff bases 1 are the important compound owing to their wide range of biological activities and industrial application. They have been found to posses the pharmacological activities such as antibacterial,2-4 antifungal,2,4-6 anticancer,2,3 anti HIV,7 antitubercular8, antiviral,2,9 antiinflammetry,10 anticonvulsant 11 and antimalarial.12 Schiff bases are used as starting material for the synthesis of various heterocyclic compounds. The presence of various substituents in the phenyl rings of aromatic Schiff bases 13 are responsible for antifungal activity, which can be changed depending upon the type of substituent present on the aromatic rings. In view of these above biological importance of Schiff bases, we have synthesized some new Schiff bases evaluated for their bioactivity. New Schiff bases were synthesized by refluxing the reaction mixture of 4-iodoaniline, 4chloroaniline, p-toluidine with halogenohydroxy substituted acetophenones in methanol 14 in the presence of glacial acetic acid . All the synthesized compound were characterized on the basis of their IR, H1NMR, mass spectral and halogen, nitrogen analysis. The antibacterial and antifungal activity of compounds was evaluated by agar diffusion method and poison plate method respectively. 2. Materials and Method 2.1. Experimental All the chemicals used were of analytical grade (AR). Melting points of the synthesized compounds were determined by open capillary and are uncorrected. The purity of the compounds was checked by TLC using silica gel plates and spots were developed in iodine chamber, IR spectra were recorded with KBr pellets on Shimadzu FTIR model 8400 spectrophotometer, H1NMR spectra in CdCl3 on a Varian NMR mercury-300 instrument, Mass spectra were recorded on VG 7070H mass spectrometer. 2.1.1. General procedure for synthesis of Schiff bases A mixture of 4-iodoaniline, 4-chloroniline / p-toluidine (0.01 mol) and halogenohydroxy substituted acetophenone (0.01 mol) in 15 ml of methanol and (0.5ml) glacial acetic acid was refluxed for 4 hrs, Published under licence by IOP Publishing Ltd

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ScieTech 2013 Journal of Physics: Conference Series 423 (2013) 012006

IOP Publishing doi:10.1088/1742-6596/423/1/012006

then the reaction mixture was left stand for overnight. The solid separates out. Separated solid was filtered, dried and recrystallised by ethanol. Scheme

Comp.

R1

R2

R3

Ia

I

Cl

I

Ib

Br

Cl

I

Ic

I

CH3

I

Id

Br

CH3

I

IIa

I

Cl

CH3

IIb

Br

Cl

CH3

IIc

I

CH3

CH3

IId

Br

CH3

CH3

IIIa

I

Cl

Cl

IIIb

Br

Cl

Cl

IIIc IIId

I Br

CH3 CH3

Cl Cl

Synthesis of Schiff bases (Ia-IIId) 1-(5’-chloro-2’-hydroxy-3’-iodophenyl) ethylidene-4-iodoaniline (Ia) ;Yield 77 %, Greenish yellow, m.p. 188 0C; IR (KBr cm-1): 1612 (-C=N), 1550(C=C), 3213-3065 (phOH). 1HNMR (δ, ppm): 2.35(s, 3H, CH3), 6.67-7.86 (m, 6H, Ar-H).12.95 (s,1H,OH);MS (m/z): 497. Calcd.for C14H10ONClI2 : I and Cl, 58.19; N, 2.81 Found I and Cl, 58.26, N, 2.89. 1-(3’-bromo-5’-chloro-2’-hydroxyphenyl) ethylidene-4-iodoaniline (Ib) ;Yield : 80 %, Yellow, m.p. 1800C; IR (KBr cm-1): 1612 (-C=N), 1550(C=C), 3213-3065 (ph-OH). 1 HNMR (δ, ppm): 2.35(s, 3H, CH3), 6.67-7.86 (m, 6H, Ar-H), 11.55 (s,1H, OH); MS (m/z): 450 Calcd.for C14H10ONClBrI : Cl, Br and I, 53.83, N, 3.11 Found Cl, Br and I, 53.76, N, 3.17. 1-(2’-hydroxy-3’-iodo-5’-methylphenyl) ethylidene-4-iodoaniline (Ic) ;Yield 75 %, Yellowish white, m.p. 150 0C; IR(KBr cm-1): 1628 (-C=N), 1550(C=C), 3243-3015 (phOH); 1H NMR (δ, ppm): 2.45(s, 3H, CH3), 2.36(s, 3H, CH3),6.60-7.81 (m,6H,Ar-H); 12.25 (s, 1H, OH); MS (m/z): 477 Calcd.for C15H13ONI2 : I, 53.25, N, 2.93. Found I, 53.32, N, 2.85 1-(5’-chloro-2’-hydroxy-3’-iodophenyl) ethylidene-4-methylaniline (IIa) ;Yield 70 %, Yellow, m.p. 137 0C IR (KBr cm-1): 1612 (-C=N), 1506(C=C), 3450-3030 (ph-OH); 1H NMR (δ, ppm): 2.38(s, 3H, CH3), 2.37(s, 3H, CH3), 6.83-7.84 (m, 6H, Ar-H). 12.40 (s,1H,OH); MS (m/z): 385 Calcd.for C15H13OClNI: Cl and I, 42.21, N, 3.64 Found: Cl and I, 42.28. N, 3.67 1-(3’-bromo-5’-chloro-2’-hydroxyphenyl) ethylidene-4-methylaniline (IIb);Yield 78 %, Yellow, m.p. 105 0C IR (KBr cm-1): 1645 (-C=N), 1435(C=C), 3080 (ph-OH).1H NMR (,δ ppm): 2.37(s, 3H, CH3), 2.31(s, 3H, CH3),6.683-7.75 (m, 6H, Ar-H), 12.86 (s, 1H, OH).MS (m/z): 338 Calcd.for C15H13ONClBr : Cl and Br, 34.17, N, 4.14. Found : Cl and Br, 34.22, N, 4.08

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ScieTech 2013 Journal of Physics: Conference Series 423 (2013) 012006

IOP Publishing doi:10.1088/1742-6596/423/1/012006

1-(2’-hydroxy-3’-iodo-5’-methylphenyl) ethylidene-4-methylaniline (IIc);Yield 75 %, Dark yellow m.p. 110 0C IR (KBr cm-1): 1597 (-C=N), 1504(C=C), 2914 (ph-OH).1H NMR (δ , ppm): 2.66 (s, 3H, CH3), 2.38 (s, 3H, CH3), 2.37 (s, 3H, CH3), 6.84-7.71 (m, 6H, Ar-H). 12.65 (s,1H,OH), MS (m/z): 365 Calcd.for C16H16ONI : I, 34.79 N, 3.84. Found : I, 34.85, N, 391. 1-(5’-chloro-2’-hydroxy-3’-iodophenyl) ethylidene-4-chloroaniline (IIIa) ;Yield 80 %, pale yellow, m.p. 112 0C; IR (KBr cm-1): 1614 (-C=N), 1552(C=C), 3220-3065 (ph-OH). 1 HNMR (δ, ppm): 2.36(s, 3H, CH3), 6.70-7.85 (m, 6H, Ar-H).12.85 (s,1H,OH); MS (m/z): 406. Calcd.for C14H10ONCI2I : I and Cl, 48.77; N, 2.81 Found I and Cl, 48.15, N 2.35. 1-(3’-bromo-5’-chloro-2’-hydroxyphenyl) ethylidene-4-chloroaniline (IIIb) ;Yield : 75 %,pale Yellow, m.p. 1410C; IR (KBr cm-1): 1615 (-C=N), 1548(C=C), 3218-3060 (phOH). 1HNMR (δ, ppm): 2.32(s, 3H, CH3), 6.72-7.89 (m, 6H, Ar-H), 12.35 (s,1H, OH); MS (m/z): 359 Calcd.for C14H10ONCl2Br : Cl, and Br,42.06, N, 3.11 Found : Cl, and Br,41.88, N 2.82. 1-(2’-hydroxy-3’-iodo-5’-methylphenyl) ethylidene-4-chloroaniline (IIIc) ;-Yield 70 %, Yellowish white, m.p. 98 0C; IR(KBr cm-1): 1625 (-C=N), 1545=C), 3243-3015 (ph-OH); 1H NMR (δ, ppm): 2.45(s, 3H, CH3), 6.60-7.81 (m,6H,Ar-H); 12.25 (s, 1H, OH); MS (m/z): 385 Calcd.for C15H13ONICI : I and Cl, 42.21,N,3.64 Found: I and Cl, 41.98, N,3.44. 2.1.2. Biological activity Antimicrobial (Escherishia coli, Salmonella typhi, Staphylococcus aureus and Bacillus subtilis) activity was evaluated by Agar cup method15,16 and antifungal (Aspergillus niger, Penicillium chrysogenum, Fusarium moneliforme and Aspergillus flavus) activity was evaluated by Poison plate method17 Nutrient ager was used as culture for antibacterial activity and potato dextrose ager was used as culture for antifungal activity and DMSO was used to dissolved compounds. The results of the antibacterial and antifungal activity is shown in table 1. Result shows that compounds Ib, Id, are having significant activity for Bacillus subtilis. Compounds Ib, Id and IIa showed significant activity for Escherishia coli. The compounds Ia, Ib, Id, IIa and IIb showed antifungal activity. In general compounds having chloro, bromo or iodo substitutent in their structure are having significant antibacterial and antifungal activity.

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ScieTech 2013 Journal of Physics: Conference Series 423 (2013) 012006

IOP Publishing doi:10.1088/1742-6596/423/1/012006

Table 1. Antibacterial and antifungal activity of the Schiff bases Antibacterial activity Zone of inhibition in mm Sr.

Ia Ib Id IIa IIb Penicillin Grysofulvin

Antifungal activity

E. coli

S. typhi

S. aureus

B. subtilis

A. niger

-ve 16 12 11 -ve 13 --

-ve -ve -ve -ve -ve 18 --

-ve -ve -ve -ve -ve 36 --

-ve 17 15 -ve -ve 16 --

-ve RG RG -ve RG --ve

-ve  No Antibacterial activity.

P. chryso genum

F. moneli forme

-ve -ve -ve -ve

-ve -ve -ve -ve

--ve

--ve

A. flavus forme

RG RG RG -+ve --ve

-ve  No growth, Antifungal observed. RG  Reduced growth (less active). +ve  Fungal growth, No antifungal activity.

3.

Result and discussion New Schiff bases were obtained by condensing halogenohydroxy substituted acetophenone with 4-iodoaniline, 4-chloroniline, p-toluidine. The IR spectra of the synthesized compounds showed the presence of C=N stretching bands at 1645-1597 cm-1. 1H NMR spectra of the synthesized compounds, the protons of azomethine compounds have given δ, ppm 2.30-2.37 due to -N=C-CH3 for all compounds. The element analyses of the compounds are in agreement with the composition suggested for the compounds. Mass spectroscopy was performed of all the Schiff bases to determine its molecular weight. Molecular ion peak of Schiff bases was confirming its formula weight. Which are same as the calculated molecular ion value. In accordance with the data obtained from antimicrobial activity, all the synthesized Schiff bases of halogenohydroxy acetophenone have shown good activity against the tested microbes. Among these Schiff bases of halogenohydroxy acetophenone Ib, Id, and IIa has shown good activity against all the tested bacteria and fungi. 4.

Conclusions The research study reports the successful synthesis of new Schiff bases. Schiff bases were physically and chemically characterized through elemental analysis, IR, 1H NMR, and Mass spectral data. The antimicrobial activity was tested of the Schiff bases on the strains E. coli, S. typhi, S. aureus and B. subtilis, A. niger, P. chrysogenum, F. moneliforme and A. flavus, and it was compared to the standard Penicillin and Grysofulvin. The tested compound Ib, Id and Ie are very active against both gram positive and gram negative bacteria. The compounds Ia, Ib, Id, IIa and IIb showed antifungal activity. Acknowledgements The authors are also thankful to University Grants Commission, New Delhi , India and WRO, Pune, for sanctioning Research Project to K.K.G., Director of IICT, Hyderabad, Department of

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ScieTech 2013 Journal of Physics: Conference Series 423 (2013) 012006

IOP Publishing doi:10.1088/1742-6596/423/1/012006

Chemistry Pune, Pune University Pune, for providing spectra and Mrs Shete, Head Department of Microbiology, N.S.B. College Nanded, for providing antimicrobial activity. References: [1] Wang L, Feng Y, Xue J and Li Y 2008 J. Serb. Chem Soc. 73 1-6 [2] Cerhiaro G, and Ferreira A M D 2006 Journal of the Brrazilian Chemical Society 17(8) 14731485 [3] Pandeya S N, Smitha S, Jyoti M and Sridhar S K 2005 Acta Pharmaceutica 55 27-46 [4] Sharma V K, Srivastava S and Srivastava A 2006 Polish Journal of Chemistry 80 387-396 [5] Sharma V K, Srivastava A and Srivastava S 2006 Journal of the Serbian Chemical Society 71 (8-9) 917-928 [6] Pandey S N, Lakshmi V S and Pandey A 2003 Indian J. Pharm. Sci. 65 213-222 [7] Bal T R, Anand B, Yogeeswari P and Sriram D 2005 Bioorganic and Medicinal Chemistry Letters 15(20) 4451-4455 [8] Bhat M A, Imran M, Khan S A and Siddiqui N 2005 J. Pharm Sci 67 151-159 [9] Karthikeyan M S, Dasappa J P, Boja P, Subrahmanya, Bhat K, Bantwal S H 2006 Bioorg and Med Chem 14 7482-7489 [10] Wadher S J, Puranik M P, Karande N A and. Yeole P G 2009 International Journal of Pharm Tech Research 1 22-33 [11] Chinnasamy R P, Sundararajan R and Govindaraj S 2010 International Journal of Pharmacy and Pharmaceutical 2 (4) 177-181 [12] Li Y, Yang Z S, Zhang H, Cao B J and Wang F D 2003 Bio org and Med Chem 11 4363-4368 [13] Manrao M R, Gill K K, Sharma J R, Kalsi P S 2000 Pestic. Res. J. 12 239-241 [14] Sridhar S K, Sarvanan M and Ramesh A 2001 Eur. J. Med. Chem. 36 615 [15] Collins C H 1967 Microbiological Methods (Butterworth, London) p 364 [16] Godkar P B Text Book of Medical Laboratory Technology 1996 (Bhalavi Publication House, Mumbai, India) p 326 [17] Robert Cruickshant A Practice of Medicinal Microbiology Vol. II

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