International Journal of Chemtech Research

B.S. Vatkaret al/Int.J. ChemTech Res.2010,2(1)

International Journal of ChemTech Research

CODEN (USA): IJCRGG ISSN: 0974-4290

Vol.2, No.1, pp504-508, Jan-Mar 2010

Synthesis and Antimicrobial Activity of Some Flavanone Derivatives

B.S. Vatkar*1, A.S. Pratapwar2, A.R. Tapas2, S.R. Butle1

and Balkrishna Tiwari1

1School of Pharmacy, S.R.T.M.University, Nanded - 431606, (M.S.), India.

2S.N. Institute of pharmacy, Pusad- 445204 (M.S.), India.

*Corresponding author:

Mobile No: 919403389262

ABSTRACT: Flavanone has been used widely for their antimicrobial and antifungal property. The Chalcones were reported by Claisen-Schmidt condensation of substitutedacetophenone with substituted aromatic aldehydes. Various analogs of flavanone were synthesized from by oxidative cyclization of chalcones withsatisfactory yield and purity.All the title compounds characterized on thebasis of their IR, 1H NMR, Massspectroscopic data.All analogues of 2,3-dihydro-2-phenylchromen-4-one have shown moderate to good antimicrobial and antifungal property by the Filter paper disc method.

KEY WORDS: Synthesis, Flavanone, Benzopyran, Antimicrobial activity.

B.S. Vatkaret al/Int.J. ChemTech Res.2010,2(1)

INTRODUCTION

Due to the rapid development of bacterial resistance to antibacterial agents, it is vital to discover novel scaffold for the design and synthesis of the new antibacterial agents to help in the battle against pathogenic microorganisms. Much research has been carried out with the aim to discover the therapeutic values of flavanone derivatives.

Flavones which are also known as anthoxanthins, are widely distributed as yellow coloured plant pigment (flavus, latin meaning yellow) and occur either in the free state or as glycosides associated with tannins. The derivatives of phenol present as glycosidal form and chemically they are derivatives of phenyl benzo-Y-pyrone (chromone) ring. The basic flavanoid structure is a flavone nucleus,In nature, they are available as flavone, flavonol, flavanone, isoflavone, chalcone and their derivatives.1Natural and synthetic flavanoids and flavanones have attracted considerable attention because of their interesting biological activity including antimycobacterial,2 antimicrobial,3,4 anti-lung cancer,5antibacterial,6antiproliferative,7anti-Tuberculosis,8 antifungal,9 antiarrhythmic,10 antiviral,11

antihypertensive,12Antioxidant,12Anti-inflammatory.12Flavonoids have created a more attention of researcher with the discovery of the French Paradox, i.e.decrease incidence of cadio-vascular disease observed in Mediterranean population, in association with red wine consumption and a greater amount of saturated fat than average diet in other countries.12,13In the present work we report the reaction of various substituted acetophenone with different substituted aromatic aldehyde to form Chalcones. Various analogs of flavanone were reported by oxidative cyclization of Chalcones. The structures of the various synthesized compounds were assigned on the basis of IR, 1H-NMR spectral data. These compounds were also screened for their antimicrobial activity.

EXPERIMENTAL

Melting points were determined on SUPERFIT melting point apparatus in open capillary tubes and are uncorrected. The IR spectra were recorded in KBr on SHIMADZU FT-IR – 8400 spectrophotometer. The 1H-NMR were recorded in CDCl3 on a Varian mercury YH-300 NMR Spectrometer using TMS as an internal standard. The purity of the compounds was checked by TLC-using Silicagel-G (Merck). Column chromatography was performed on Silica gel (Merck, 60-120 mesh).

General procedure for the preparation of chalcone (IIIa-f)

A mixture of substituted acetophenones (0.01 mole) and aryl aldehydes (0.01 mole) was stirred in ethanol (30 mL) and then an aqueous solution of potassium hydroxide (15 mL) was added to it. The mixture was kept over night at room temperature and then it was poured into crushed ice and acidified with dilute hydrochloric acid. The chalcone derivative precipitates out as solid. Then it was filtered and crystallized from ethanol.14

General procedure for the synthesis of flavanones from chalcone ( IVa-f)

Substituted chalcones (0.001 mol) dissolved in methanol (50 ml) in a 200 ml beaker. The resulting solution was made alkaline (pH 10.0) with potassium hydroxide pellets and was allowed to react for 2—3 h at room temperature (the reaction time for different chalcones vary from 1—3 h). The reaction mixture was then acidified (using 10% aqueous hydrochloric acid: ice-cold) to precipitate the flavanones. The product was filtered with suction on a Buchner funnel, washed with cold water until the washings were neutral to litmus and then with 5 ml of ice-cold rectified spirit. The dried product was recrystallised from 95% ethanol.1

B.S. Vatkaret al/Int.J. ChemTech Res.2010,2(1)

Compound code / R1 / R2 / R3

IVa

/ H / NO2 / H
IVb / H / H / F
IVc / H / H / CH3
IVd / OH / OH / H
IVe / OH / NO2 / H
IVf / OH / H / CH3

Table 1. Characterization and Spectral data of compounds IVa-f

Compound code

Mol. formula

M.P. C

Rf value

IR (Cm-1, KBr)

1H NMR (CDCl3/ (ppm)

IVa /

C15H11NO4

174-176C

0.65

/ 1492 (CNO2),1720 (C=O),
1527 (CH=CH),
1197 ( C-O-C). / 3.8(d,2H,O=C-CH2), 5.8(t,1H,O-CH),7-8.1(m,4H,5,6,7,8 -Ar-H), 8.2-8.6(m,4H,2’,4’,5’,
6’-Ar-H)
IVb /

C15 H11 FO2

168-170C

0.82

/ 840 (C-F), 1710(C=O),
1595 CH=CH), 1105(C-O-C). / 3.7(d,2H,O=C-CH2),5.6(t,1H,O-CH),6.5-7.4(m,4H, 5,6,7,8-Ar-H),7.58.0(m,4H,2’,3’,5’,6’-Ar-H)
IVc /

C16 H14O2

182-184C

0.78

/ 1677(C=O),
1566(CH=CH),
1157(C-O-C). / 2.4(S,3H,CH3)3.7(d,2H,O=CCH2),5.6(t, 1H,O-CH),6.8-7.4(m,4H,5,6,7,8-Ar-H),7.5-8.0(m,4H, 2’,3’,5’,6’-Ar-H)
IVd /

C15 H12O4

192-194C

0.76

/ 3068(OH),
3089(OH),
1708(C=O),
1587(CH=CH),
1103(C-O-C). / 3.2(d,2H,O=C-CH2), 5(s,2H,3’,7-OH),5.4(t,1H,O-CH),
6.8-7.5(m,3H,5,6,8-Ar-H),7.67.9(m,4H,2’,3’,5’,6’-Ar-H)
IVe /

C15H11NO5

202-204C

0.80

/ 3043(OH),
3066(C-NO2),
1706(C=O),
1589(CH=CH),
1103(C-O-C). / 3.6(d,2H,O=C-CH2), 4.9(s,1H,7-OH),
5.8(t,1H,O-CH),
6.3-6.6(m,3H,5,6,8-Ar-H),6.8-7.1(m,4H, 2’,4’,5’,6’-Ar-H)
IVf /

C16 H14O3

168-170C

0.71

/ 3070(OH),
3004(C-CH3),
1739(C=O),
1512(CH=CH),
1141(C-O-C). / 2.4(s,3H,CH3),3.7(d,2H, O=C-CH2), 5.6 (t; 1H,O-CH) 5(s,1H, 7-OH)6.9-7.3 (m,3H, 5,6,8-Ar-H),7.4-8.0 (m,4H,2’,4’,5’,6’-Ar-H)

Table No. 2 Antimicrobial Activity of derivatives

Compounds / Antibacterial* / Antifungal*
E. c. / P. a. / A. n. / A. f.
IV a / 08 / 13 / 09 / 10
IV b / 09 / 08 / 12 / 08
IV c / 07 / 08 / 11 / 09
IV d / 08 / 10 / 10 / 10
IV e / 07 / 11 / 08 / 08
IV f / 07 / 09 / 09 / 12
Streptomycin / 18 / 15 / -- / --
Fluconazole / -- / -- / 13 / 15

*Zone of inhibition was measured in mm. Escherichia coli (E.c.), Pseudomonas aeruginosa (P.a), Aspergillus niger (A.n.), Aspergillus flavus (A.f.).

B.S. Vatkaret al/Int.J. ChemTech Res.2010,2(1)

ANTIMICROBIAL ACTIVITY:

The synthesised compounds (IVa-IVf) were screened for their in vitro antimicrobial activity against Escherichia coli, Pseudomonas aeruginosa and antifungal activity against Aspergillus niger, Aspergillus flavus, by measuring the zone of inhibition in mm. The antimicrobial activity was performed by filter paper disc plate methodat concentration 100 µg/mL and reported in Table-2. Muller Hinton agar & Sabouroud Dextrose agar were employed as culture medium and DMSO was used as solvent control for antimicrobial activity.Streptomycin and Fluconazole were used as standard for antibacterial and antifungal activities respectively.

CONCLUSION

The structure of the synthesized substituted flavanones were confirmed from their respective spectral data such as IR,1H NMR Studies,From the antimicrobial screening it was observed that all the compounds exhibited activity against all the organisms employed. The Antibacterial activity of all compounds against tested microorganism have been found that compound No.IVa,IVb,IVd,IVe possessed good antibacterial activity, Other analogues of 2,3-dihydro-2-phenylchromen-4-one have shown moderate antibacterial activity. Antifungal activity of all compounds found that compound No. IVa,IVb,IVc,IVd,IVf have been found to be good antifungal activity. Other analogues of 2,3-dihydro-2-phenylchromen-4-one have shown moderate antifungal activity.As we consider all results obtained from antibacterial and antifungal tests together we can say that entire compounds tested are active towards bacteria and fungi.

ACKNOWLEDGEMENT

The author are thankful to Dr D. U. Gawai H.O.D.Depatment Of Microbiology, Botany and Biotechnology, Science College Nanded for their help in analyzing the Antimicrobial activityand to the Director SHIMADZU Analytical Center and NMR Facility, Department Of Chemistry, University Of Pune for providing NMR and also thankful to Mr A.A.Kulkarni,Lecturuer,Padm.D.Y. Patil Institute of Pharmaceutical Sciences and Reasearch. Pune for providing IR facility.

B.S. Vatkaret al/Int.J. ChemTech Res.2010,2(1)

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