High-Throughput Catch-and-Release Synthesis of Oxazoline Hydroxamates. Structure-Activity Relationships in Novel Inhibitors of Escherichia coli LpxC: In Vitro Enzyme Inhibition and Antibacterial Properties was written by Pirrung, Michael C.;Tumey, L. Nathan;McClerren, Amanda L.;Raetz, Christian R. H.. And the article was included in Journal of the American Chemical Society in 2003.COA of Formula: C9H9ClO2 This article mentions the following:
LpxC is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram-neg. bacteria. Oxazolines incorporating a hydroxamic acid, which is believed to coordinate to the single essential zinc ion, at the 4-position are known inhibitors of this enzyme. Some of these enzyme inhibitors exhibit antibacterial activity through their inhibition of LpxC. A method has been developed for the synthesis of oxazolines using resin capture and ring-forming release that eliminates traditional purification steps and can be used in high-throughput synthesis. Using this method, oxazoline hydroxamates with diverse 2-substituents were prepared in library form as candidate inhibitors for LpxC. Two conventional methods for oxazoline synthesis were also applied to generate more than 70 compounds The groups at the 2-position included a wide variety of substituted aromatic rings and a limited selection of alkyl groups. These compounds were screened against wild-type and LpxC inhibitor-sensitive strains of Escherichia coli, as well as wild-type Pseudomonas aeruginosa. Inhibition of the E. coli LpxC enzyme was also investigated. A broad correlation between enzyme inhibitory and antibacterial activity was observed, and novel compounds were discovered that exhibit antibacterial activity but fall outside earlier-known structural classes. In the experiment, the researchers used many compounds, for example, 2-(3-Methoxyphenyl)acetyl chloride (cas: 6834-42-0COA of Formula: C9H9ClO2).
2-(3-Methoxyphenyl)acetyl chloride (cas: 6834-42-0) belongs to organic chlorides. Organochlorines stimulate the central nervous system and cause convulsions, tremor, nausea, and mental confusion. Examples are dichlorodiphenyltrichloroethane (DDT), chlordane, lindane, endosulfan, and dieldrin. Alkyl chlorides readily react with amines to give substituted amines. Alkyl chlorides are substituted by softer halides such as the iodide in the Finkelstein reaction.COA of Formula: C9H9ClO2
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics