Green Synthesis of Novel Chalcone Derivatives, Characterization and its Antibacterial Activity

M. Sandhya Rani*, C. Rohini, B. Sai keerthi, C. Mamata.

Pulla Reddy Institute of Pharmacy, Sy. No 167,168, Near Dundigal Airforce Academy,

Annaram (V), Jinnaram (M), Medak Dist.

*Corresponding Author E-mail: sandhya.madala@gmail.com

Abstract:

In an effort to develop antimicrobial agents, a series of chalcones were prepared by Claisen – Schmidt condensation by trituration method. Appropriate acetophenones with appropriate aromatic aldehydes in the presence of aqueous solution of sodium hydroxide and ethanol at room temperature. The synthesized compounds were characterized by means of their IR, ‘H-NMR spectral data. All the compounds were tested for their antibacterial activities by the cup plate method.

KEY WORDS: Chalcone, synthesis, Antibacterial activity.

INTRODUCTION:

Chalcones are well known intermediates for synthesizing various heterocyclic compounds. Chalcones are also known as benzylacetophenone these are precursor compounds of flavonoids occurs in medicinal plants and they can also be synthesized through laboratory^[1]. chemically chalcones are 1,8 – diphenyl-2- propene-1- one derivatives in which two aromatic rings are linked by a ‘3’ carbon alpha and beta unsaturated carbonyl system^[2-3]. The compounds with backbone of chalcones have been reported to posses various biological activities such as antimicrobial^[4], anti-inflammatory^[5], analgesia^[6] antiplatelet^[7], antiulcerative^[8], antimalarial^[9], anticancer^[10]antiviral^[11]antileishmanial^[12]antioxidant^[13], antitubercular^[14], antihyperglycemic^[15] immunomodulatory^[16], inhibition of chemical mediators release^[17]inhibition of leukotriene B4^[18], inhibition of tyrosinase^19], and inhibition of aldose reductase activities. The presence of reactive α, β –unsaturated keto function in chalcones is found to be responsible for their antimicrobial activity. These compounds were also screened for their antimicrobial activity.

EXPERIMENTAL:

Melting points were determined in open capillary tubes and are uncorrected. The IR spectra were recorded in DMSO on Perkin – Elmer BX spectrophotometer. The H-NMR was recorded in DMSO on bruker spectrospin AV 400 MHz spectrometer using TMS as an internal standard. The elemental analyses were performed on carlo Erba 1108 elemental analyzer. The purity of the compounds was checked by TLC- using silicagel-G.

General Procedure for the synthesis of chalcone derivatives:

Both benzaldehyde derivatives and acetophenone derivatives where taken in mortar pestle triturated with NaoH powder added in portion wise with continuous trituration. 2- Hydroxy acetophenone was added with continuous trituration. A solid yellow mass was formed maintenance given for 10-15 min. The formed yellow solid was immediately was washed with hot methanol to get crude chalcone. After TLC conformed that SM was absent hot methanol was added. Then filtration was done by using hot methanol.

SCHEME:

RESULTS AND DISCUSSION:

Compound	Melting point	Yield	Molecular formula	Molecular weight	IR. Vmax Cm^-1
Compound	Melting point	Yield	Molecular formula	Molecular weight	C=C	=C=O
BDR	80-82 ˚C	60%	C₁₅H₁₂O₂	224	1629	1745
FDR	80-82 ˚C	55%	C₁₅H₁₁O₂F	242	1440	1745
ADR	80-82 ˚C	52%	C₂₀H₁₆O₃	304	1629 1442	Aliphatic Aromatic

COMPOUND-1 (BDR)

1-[2-hydroxy Phenyl]- 3-[phenyl-2-en-1-one]; pale yellow Solid; M.P (80-82ºC),% yield (60%) ; R_fvalue (6.59); FTIR(1629(C=C str); 1745( C=C str)

COMPOUND-2(FDR)

1-[2-hydoxy pheny]-3-[4-methoxy phenyl] prop-2-en-1-one];pale yellow solid; M.P (80-80ºC); % yield (55%); R_fvalue (0.35); FTIR[1440(C=C str); 1745(C=O str) H'NMR DMSO -D₆,δppm). 8.50(d,1H), 7.92 (dd,1H), 7.67 (dd,2H), 7.49 (dd,1H), 7.37 (m,1H), 7.22 (t,2H), 7.06 (t,1H), 6.86 (m,1H).

COMPOUND-3(ADR)

1-2[-HydroxyPhenyl]-3-[4-mcthoxyphenyl]prop-2-en-1-one];pale yellow ;M.P (80-80ºC);% yield (52%), R_f Value (0.08); FTIR[1629(Aliphatic); 1442(Aromatic): H'NMR DMSO-D₆,δppm): 8.51(d,1H), 7.89 (m,2H), 7.89 (m,2H), 7.61 (m,1H), 7.54 (m,1H), 7.48 (dd,2H), 7.37 (m,1H), 7.28 (m,3H), 6.99 (m,1H), 6.45 (m,1H), 6.11 (m,1H), 2.49 (m,3H).

Antibacterial Activity:

All the compounds synthesized in the investigation were screened for their antibacterial activity by subjecting the compounds to standard procedure. Antibacterial activities were tested on nutrient medium against Escheria coli which are representative types of gram negative organisms respectively. The antibacterial activity of the compounds was assessed by cup-plate method.

Preparation of Nutrient Agar Media:

Nutrient agar medium: 2.8g

Distilled water: Make upto 100 ml

Preparation of Test Solutions:

0.1mg of compound dissolved in 100ml of distilled water. From this 1ml of solution was taken and diluted up to 10ml with distilled water. Now the concentration of the test solution was 1mg/ml.

Preparation of Standard Antibiotic Solution:

Amikacin was used has standard antibiotic for comparision and solutions were prepared by using steriled water, as they was water - soluble. The solutions are diluted by using steriled water so that the concentrations of the solutions was 1mg/ml.

Compound	Minimum inhibitory concentration	Diameter (mm)
BDZ	250 µg/ml	0.5 mm
ADZ	160 µg/ml	1 mm
FBZ	120 µg/ml	1.5 mm
Standard	3 µg/ml	3 mm

CONCLUSION:

· All the three synthesized chalcone derivatives has antibacterial activity against E.coli, among them fluoro derivative having much more antibacterial activity than other two derivatives.

· May be further synthesis of novel chalcone derivatives will be much more potent and beneficial.

REFERENCES:

1. Vishwanadham Yerrangunta. Pharmatutor IIS:2347-7881.

2. D. Azarifar. Indian Journal of Chemistry- B vol 43B pp 1580-1584.

3. M. Vijay Bhaskar Reddy. Med Chem 2008 isn`t 883-1584.

4. Mokle S. S Sayeed M. A. Kothawar and Chopde, Int.J. Chem, Sci 2004, 2 (1).96

5. Hsieh H K, Tsao L T and Wang J P, J, Pharm, Pharmacol., 2000, 52, 163.

6. Viana G S, Bandeira M A. and Matos F, J. Phytomedicine, 2003, 10, 189.

7. Zhao L M, Jin H S, Sun L P, P Iao H R and Quan ZS. Bioorg, Med, Chem, Lett, 2005, 15. 5027.

8. Mukaeami S, Muramatsu M, Aihara H and Otomo S, Biochem, Pharmacol, 1991,42,1447.

9. Liu M, Wilairat P and Go I .M, J. Med Chem,2001, 44,4443.

10. Francesco E, Salvatore G, Luigi M and Massimo C, Phytochem, 2007, 68,939.

11. Onyilagna J C, Malhotra B, Elder M and Towers G H N, Can. J. Plant Pathol, 1997, 19, 133.

12. Nielsen S F. Chen M. Theander T G, Kharazmi A and Christensen S B, Bioorg, Med, Chem, Len, 1995,5,449.

13. Miranda CL, Aponso G L M, Stevens J F, Deinzer M L and Buhler D R, J Agric, Food Chem, 2000,48,3876.

14. Siva Kumar P M, Geetha Babu S K and Mukesh D. Chem. Pharm Bull,2007, 55(1),44.

15. Satyanarayana M. Priti Tiwari, Tripathi K, Srivastava A K and Ram Pratap, Bioorg . Med, Chem,2004,12,883.

16. Barford L. Kemp K. Hansen M and Kharazmi A, Int, Immunopharmacol, 2002, 2,545.

17. Ko H H, Tsao L T, Yu K L, Liu C T, Wang J P and Ram Pratap, Bioorg. Med. Chem,2004,12,883.

18. Deshpande A M, Argade N P, Natu A A and Eckman, Bioorg, Med, chem,1999,7,1237.

19. Khatib S. Nerya Argade O, Musa R, Shmmel M, Tamir S and Vaya J, Bioorg, Med, Chem. 2005,13,433.

Received on 14.04.2019 Modified on 12.05.2019

Research J. Science and Tech. 2019; 11(3):183-185.

DOI: 10.5958/2349-2988.2019.00028.7