Synthesis of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane derivatives as Antimicrobial agents

Abstract

Epoxides are the natural phytoconstituents with several biological significance such as Anti-inflammatory, Antioxidant, Anticancer and Antimicrobial activity. The Series 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane derivatives was designed and synthesized from 1-(5-chloro-2-hydroxyphenyl)-3-(2-chlorophenyl)-prop-2-en-1-one.

Current research work screened forIv-vitroanti-bacterial activity against Escherichia coli, Staphylococcus aureus (Pathogens obtained from animal), Xanthomonas citri and Xanthomonas malvacearum (Pathogens obtained from plant). The compound SAC-3 and SAC-6 shows good antibacterial activity while other shows moderate to good anti-microbial activity.

Keywords

Epoxide; Chalcone; Escherichia coli; Anti-bacterial Activity

INTRODUCTION

Chalcones are the natural phytoconstituents widely distributed in plants originate in fruits, vegetables, grains, bark, roots, stems and flowers. The different derivatives of chalcones were synthesized from chalcones with marked biological significance such as Antibacterial, Antifungal, Antimalaria, Anti-inflammatory, Anticancer and Antitubercular activity. Hence, Chalcones are considered as an indispensable component in a variety of nutraceutical, pharmaceutical, medicinal and cosmetic applications with versatile health benefits [1-3].

In organic chemistry epoxides are valuable building blocks in the synthesis of many important reactions for derivatization. Basically for the preparation of surfactants, corrosion protection agents, additives to laundry detergents, lubricating oils, textiles and cosmetics epoxides are play important role in industry.

Present research a novel 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC: 2 to 6) series of synthetic epoxide have been synthesized. Synthesis of novel derivatives is carried out using 1-(5-chloro-2-hydroxyphenyl)-3-(2-chlorophenyl) -1-oxo-2-propene as starting material and followed by to evaluate antimicrobial activity [4,5].

MATERIALS AND METHODS

Melting points were determined in an open capillary tube and are uncorrected. IR spectra were recorded in KBr on a Perkin-Elmer spectrometer. 1H NMR spectra were recorded on a Gemini 300-MHz instrument in Dimethyl Sulfoxide (DMSO) as solvent and TMS as an internal standard. The purity of products was checked by Thin Layer Chromatography (TLC) on silica gel [6-10].

Synthesis Scheme (Figure 1)

Synthesis of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC: 2 - 6)

Take 0.01 ml (0.293 g) of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chlorophenyl) -1-oxo-2-propene (SAC:1) and 25 ml of ethanol in a dry conical flask followed by 10 ml of 5% NaOH. Stir reaction mixture until chalcone get completely dissolved. Add 5 ml of 30% hydrogen peroxide in above reaction mixture and stir the reaction mixture for 2 Hrs. Collect the separated solid, filtered, washed with cold water and recrystallized from ethanol. All SAC: 2-6 were synthesized by same reaction mechanism (Figure 2) [11-17].

RESULTS AND DISCUSSION

Spectral Data of 1-(5-Chloro-2-hydroxyphenyl)-3-(2-chlorophenyl)-1-oxo-2,3-epoxy propane (SAC-2):
IR: ѵ max (cm^-1): 3120 (OH), 1640 (C=O), 1682, 1585 (C=C aromatic).
1H NMR: δ 4.3 (d, 2H, CH), 4.45 (d, 2H, CH), 12.3 (s, 1H, OH), 7.56 (m, 3H, ArH), 7.95 (m, 4H, ArH).
Spectral Data of 1-(5-Chloro-2-hydroxy-4-methylphenyl)-3-(2-chlorophenyl)-1-oxo-2,3-epoxy propane (SAC-4):
IR: ѵ max (cm^-1): 3125 (OH), 1640 (C=O), 1680, 1595 (C=C aromatic).
1H NMR:δ 4.43 (d, 2H, CH), 4.40 (d, 2H, CH), 12.35 (s, 1H, OH), 2.33 (s, 3H, CH3), 7.61 (m, 2H, ArH), 7.20 (m, 4H, ArH) (Table 1,2).

BIOLOGICAL SCREENING

Antibacterial Activity: The newly synthesized 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC-2 to SAC-6)were screened for antibacterial activity against Escherichia coli, Staphylococcus aureus (Pathogens obtained from animal), Xanthomonas citri and Xanthomonas malvacearum (Pathogens obtained from plant) using Disc Diffusion Method11. The Filter paper discs were soaked in solution of different compounds at concentration of 100 ppm [18-25]. The solvent aqueous DMF (5% 1ml) used for preparing solution of the compounds. The disc soaked in solution of compound placed at the center of bacteria seeded nutrient agar plates (Petri dishes). The Petri dishes were incubated at 26± 1°C for 24 hrs. The strength is reported by measuring the diameter of zone of inhibition in mm and results were standardized against tetracycline. The zone of inhibition was measured and reported in table 3.

CONCLUSION

The series of 1-(5-chloro-2-hydroxyphenyl)-3-(2-chloro phenyl)-1-oxo-2,3-epoxy propane (SAC-2 to SAC-6) and derivatives have synthesized by conventional method and further screened for biological activity. All the compounds showed potent antibacterial activity [26-31].

ACKNOWLEDGMENT

Authors gratefully acknowledge to Raosaheb Patil Danve College of Pharmacy Badnapur, Dist. Jalna, Dr. Babasaheb Ambedkar Technological University Lonere, Raigad for providing laboratory facilities. Authors are also thankful to Principal, Teaching and Non-Teaching Members of Raosaheb Patil Danve College of Pharmacy Badnapurfor supporting in all work.

Conflict of interest statement

The authors report no conflict of interest.