###### Abstract  
Several oxidative processes are related to a wide range of human chronic and degenerative diseases, like [PERSON]'s disease, which also has been related to cholinergic processes. Therefore, search for new or improved antioxidant molecules with acetylcholinesterasecholinesteraseerase activity is essential to offer alternative chemotherapeutic agents to support current drug therapies. A series of chalcone (**2a-2k**) and flavone (**3a-3k**) analogs were synthesized, characterized, and evaluated as acetylcholinesterasecholinesteraseerase (AChE) inhibitors, and antioxidant agents using 1,1-diphenyl-2-picrylhydrazyl (DPPH*), 2-2'-azino-bis-(3-ethylbenzothazoline-6-sulfonate) (ABTS*), and \(\beta\)-carotene/linoleic acid bleaching assay. Compounds more active were **3j** and **2k** in DPPH with EC\({}_{50}\) of 1 \(\times\) 10\({}^{-8}\) and 5.4 \(\times\) 10\({}^{-3}\)\(\mathrm{  
whether through an increase in ROS levels or a decrease in the cellular antioxidant capacity, oxidative stress occurs [2], which disturbs cellular metabolism, damages cellular constituents, and triggers the activation of specific signaling pathways [3]. The pathogenesis of several chronic and degenerative human diseases, including cardiovascular, neurodegenerative, and cancerous ones, has been linked to a cellular condition exhibiting oxidative stress [4; 5]. To counteract this stressful condition, the human body has several mechanisms and produces a broad variety of antioxidants [6], which together quench ROS activities and reduce cellular damage [7].  
Oxidative stress plays a crucial role in the etiology and pathogenesis of neurodegenerative diseases, like Alzheimer [8]. Alzheimer's disease (AD) is globally the most common cause of dementia in adults above 60 years [9]; ageing lowers the antioxidant systems activity, leading to free radical progressive accumulation, triggering lipid peroxidation mechanisms and structural damage to proteins and DNA [10], which leads to brain tissue damage. Its progression is associated to biochemical changes, like cholinergic deficit, neuronal metabolic damage derived from the glutamate excitotoxicity, and oxidative stress [11]. Acetylcholinesteraseerase inhibitors (AChEI) are actually the best available pharmacotherapy for Alzheimer's disease symptoms treatment, increasing the levels of the acetylcholine neurotransmitter during the cerebral cortex synapses [12].  
Flavonoids comprise a large family of plant-derived structurally-related polyphenolic compounds that are classified as anthocyanin, flavonoids, chalcones, aurones, flaxanones, isoflav, flavans, flavanons, flavanols, flavanols, and flavones [13]. Flavonoids have been found to display biological activities, such as anti-inflammatory [14], hepatoprotective [15], antiulcer [16], enzyme inhibitors, such as cyclooxygenase [17], xanthine oxidase [18], lipoxygenase [19], phosphodiesteraseerase [20], as well as antiviral [21], cardioprotective [22], anticancer [23], and antioxidant [24] functions.  
Pharmacological effects of flavonoids are related to their antioxidant activity, as they are powerful antioxidants against free radicals and ROS [12]. Structurally, the free radical scavenging capacity is primarily attributed to high reactivity of their hydroxyl substituents that participate in the reaction [25]. In this context, we report the chemical synthesis of chalcone and flavone analogs with different substituents on the respective B ring (Figure 1). In addition to the mandatory molecule characterization, their antioxidant and AChE inhibition activity was evaluated by in vitro testing, to get preliminary insights regarding the structure-activity relationship, allowing for us to further develop the continuous search for new therapeutic agents.