To elucidate the complicate pathological nature of AD and discover effective therapeutic candidates, chemical reagents targeting and regulating multiple pathogenic components are necessary. For that purpose, this work illustrates rational strategies to develop flavonoids that can control various pathological factors found in AD-affected brains. A series of six flavonoids (1-6) was selected by adjusting the number and position of functional groups on the A ring, and their regulatory abilities against multiple pathogenic targets, including free radicals, AChE, metal-free Ab, and metal-Ab, were evaluated to establish the structure-activity relationship. Our Oxidative modifications of metal-free and metal-added Ab through direct interactions of 7 lead to altering their aggregation profiles. Our overall studies illustrate multidisciplinary approaches for designing small molecules with multiple functions that can be used for chemical tools or therapeutic candidates in neurodegenerative disorders, such as AD.