INTRODUCTION

1. Synthesis and Antimicrobial Evaluation of a Series of Substituted Chalcone Derivatives Jonna Amato-Ocampo, Rina Carillo, Dr. Bradley Ashburn Department of Math and Sciences, Leeward Community College, Pearl City, HI 96782 SYNTHESIS DATA RESULTS INTRODUCTION BIOLOGICAL ASSAY RESULTS In synthesizing a chalcone, the presence of an alpha, beta-unsaturated functional group will be responsible for the ability to have antimicrobial activity against Pseudomonas aeruginosa, Staphylococcus aureus, and Escherichia coli bacteria. Chalcones are the result of the Aldol Condensation Product with the starting materials of an acetophenone and a benzaldehyde and the base catalyst sodium hydroxide. Research studies and literature show chalcones to have antimicrobial activity and important because of its various biological activity such as antibacterial, antifungal, antioxidant, anti-inflammatory, and anti-tumor activity. In research, to date, only certain variations of the chloros have been synthesized and without a constant use of one element. In synthesizing 16 different variations, the chloro is utilized as the constant for this research project. SCHEME I CONCLUSION BIOLOGICAL ASSAY PROCEDURE Trends in biology date indicate that many of the synthesized chalcones were as effective as the positive control of sulfanilamide in the assays tested for antimicrobial purposes against Pseudomonas aeruginosa, Staphylococcus aureus, and Escherichia coli. Future work will be in submitting a Mars One proposal and to be selected under the University Competition Payload, which will be sent to the surface of Mars in 2018. Mueller-Hinton agar is the standard media used in each plate, at a depth of 4 mm = pipette 20 mL. Pseudomonas aeruginosa, Staphylococcus aureus, and Escherichia coli is prepared and tested using a spectrometer at 0.1 Absorbance at a wavelength of 600 nm and follows McFarland Standards. A blank is determined at a wavelength of 600 nm and 0.0 Absorbance. A lawn of each bacteria is made by a sterile swab inserted into the bacteria solution and creating a lawn on the agar turning the plate 90-degrees, four times. A sterile 8 mm borer is used to make five wells in each plate. Four of the wells will contain four of the synthesized compounds and the fifth well will contain the positive control of sulfanilamide. DMSO is the negative control. A stock solution is made from each synthesized chalcone and DMSO. A dilution is created to result in 1 mg/mL and will be used to pipette 100 µl into its corresponding well. Each plate incubation temperature is 35-37°C for a period of 48-hours. At 48-hours, a ruler is used for the measurements of zones of inhibition. . EXPERIMENTAL PROCEDURE REFERENCES Interesting trends: two different procedures have the ability to create a chalcone product that will result in anti-microbial activity that can be measured by yield. Many of the steric compounds that had low yields using aqueous NaOH and ethanol, were successful created through using a solvent-free procedure of a solid sodium hydroxide through use of mixing by mortar and pestle. When a chalcone was difficult to synthesize, using a solvent-free method minimized the possibility of self-condensation of the ketone. The starting materials of the aldehyde plus the ketone, then adding the catalyst of the solid sodium hydroxide minimizes self-condensation of the ketone, resulting in a higher yield of the Aldol Condensation Product. A biological assay is used to measure the zone of inhibition, which determines the effectiveness of the lab synthesized products. Explanation for low yields may be the result of the steric effect of the chloro atom, a reaction that did not go to completion and may still contain starting materials, and the compound reacting with itself (self-condensation). Possible impurities in the final product may be a result of an alcohol being present, it may be a the 1,4 addition of the enolate (the ketone) to the α,β unsaturated compound forming the Michael Reaction. Acidity increases in the presence of an electron withdrawing group, like the electronegative Halogen, chloro, drawing electrons away causing the inductive effect. • Apalangya,Vitus A.; Bakupog, Thomas; Tutson, Charmaine; Sefadzi, Sebastian; Early, Bernadette; Troy, Roberta M.; Curry, Michael L.; Robinson, Pamela M. L.; Powell, Nicole, L.; Russell, Albert E. Inhibition of MDA-MB-231 Breast Cancer Cell Proliferation by Simple Diphenyl Chalcone and Its Chlorinated Derivatives. Research & Reviews: A Journal of Oncology and Hematology. 2012, 1, 7-12. • Baba, Haruna; Azubike, Odigwe; Usifoh, Cyril O. Synthesis and Antimicrobial Evaluation of Some Chalcones. Biological Sciences and Pharmaceutical Research. 2013, 1, 22-29. • Diaz, Gabrille; Dr. Burke, Valerie. Synthesis of Tyrosinase Inhibitors; Designing Chalcones. Saint Mary’s College of California Summer Research 2009. pp 1-30. • Kumbhar, D.D.; Waghamare, B. Y.; Pathade, G. r.; Pardeshi, S. K. Synthesis and Evaluation of Chalcones as an Anti-bacterial and Anti-fungal Agents. Der Pharmacia Lettre. 2014, 6, 224-229. • Palleros, Daniel R. Solvent-Free Synthesis of Chalcones. J. Chem Ed. 2004, 81, 1345-1347. • Paramesh, M.; Niranjan, M.S.; Sarfaraj, Niazi; Shivaraja, S.; Rubbani, M. S. Synthesis and Antimicrobial Study of Some Chlorine Containing Chalcones. Int J. Pharm Pharm Sci.2010, 2, 113-117. ACKNOWLEDGEMENTS Mahalo nui loa to Dr. Bradley Ashburn, Dr. Helmut Kae, Dr. Kabi Neupane, and Professor Alyssa Haygood for their availability, guidance, and support during the Hawaii 2014 INBRE III Summer Student Research Experience. Mahalo to Leeward Community College, Windward Community College, and Hawaii Pacific University for the use of their laboratories, Infrared Spectroscopy, and Nuclear Magnetic Resonance testing. This project was supported by a grant from the Institutional Development Award (IDeA) Networks of Biomedical Research Excellence (INBRE). The content is solely the responsibility of the authors and do not necessarily represent the official views of the National Institute of Health.