Synthesis of Pyrroloquinolone A and Derivatives

Abstract:

Pyrroloquinolone A is an organic molecule that has previously been isolated from Atractylis cancellata L. It has been demonstrated that this compound, extracted from its natural source, can inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), which may be useful in treatment of Alzheimer’s disease since lack of acetylcholine (ACh) is a major contributor to people developing the disease. Here we discuss the progress on the synthesis of pyrroloquinolone A from 2-iodoaniline using an established four-step procedure. Initial results of AChE and BChE inhibition by synthetic pyrroloquinolone A will be presented. Additionally, progress towards synthesis of derivatives of pyrroloquinolone A that can be made via the substitution of iodomethane in step 2 of the procedure for other alkyl halides will be discussed. Finally, molecular modeling of pyrroloquinolone A and its derivatives will be presented to better understand the mechanism(s) by which these molecules can interact with AChE and BChE.