Escherichia coli is among the most frequent cause of urinary tract infections, which is in turn among the infections causing the greatest morbidity in humans. Three derivatives of ciprofloxacin and one derivative of chloramphenicol is demonstrated to strongly inhibit the growth of ampicillin resistant Escherichia coli. Important pharmacological molecular properties such as Log P, polar surface area, Violations of rule of 5, and Log BB were determined. Drugs examined included the parent compound ciprofloxacin (drug A), the hexyl ester, octyl ester, and amide derivative of ciprofloxacin; drugs B, C, D, respectively. Drugs B and C are compounds that replace the initial carboxyl group (-C(O)OH) found on ciprofloxacin with a six carbon chain and eight carbon chain ester group, respectively. In addition, a chloramphenicol derivative (drug E) was synthesized to compare to the molecular properties and bacterial inhibition to the ciprofloxacin group of agents. The Log P of agents A, B, C, D, and E are determined to be -0.701, 2.007, 3.017, 2.097, and 3.343, respectively. The polar surface area of agents A, B, C, D, and E is determined to be 74.57 A², 63.58 A², 63.58 A², 75.60 A², and 74.92 A², respectively. All agents showed zero violations of the Rule of 5, indicating favorable characteristics for bioavailability and drug-likeness. Based on eight pharmaceutical properties each agent showed extremely high correlation to all other agents (Pearson r greater than 0.9800). Values of Log BB for A, B, C, D, and E are -1.07, -0.497, -0.343, -0.661, and -0.462, respectively. The ester derivatives of ciprofloxacin (drugs B and C) demonstrated analogous growth inhibition of ampicillin resistant Escherichia coli, with greater than 95% inhibition at 10 microgram/mL. The amide derivative of ciprofloxacin and the chloramphenicol derivative demonstrated greater than 85% growth inhibition of bacteria at 10 microgram/mL concentration.