Synthesis, structure and structure–activity relationship analysis of caffeic acid amides as potential antimicrobials

Triclosan-caffeic acid hybrids: Synthesis, leishmanicidal, trypanocidal and cytotoxic activities

“…Deprotection with TBAF and benzoic acid gave rise to esters 18-24 in 50-92% yields [34]. Attempts to directly obtain these compounds by coupling caffeic acid 9 with alcohols 2-8 using different coupling agents, such as EDC/HOBt [35], DCC/HOBt [36] and BOP/Et3N [37], were fruitless. On the other hand, reaction of methylated caffeic acid 25 with thionyl chloride generated the corresponding acid chloride which in turn was reacted with alcohols 2, 3, 5 and 7 to afford esters 26-29 in 40-60% yields.…”

“…Caffeic acid and some of its esters and amides derivatives exhibit a broad spectrum of biological activities including anti-inflammatory [7], antimicrobial [8,9], antioxidant [10], anti-Alzheimer [11], analgesic [12] and anticancer effects [13][14][15]. In addition, some studies have shown that caffeic acid esters have high anti-leishmanial activity [16][17][18][19].…”

Ethyl Cinnamate Derivatives as Promising High-Efficient Acaricides against <i>Psoroptes cuniculi</i>: Synthesis, Bioactivity and Structure–Activity Relationship

“…10) Due to their common occurrence in plants and their low toxicity, 11,12) cinnamic acid derivatives have attracted much attention of many pharmacologists. In the past decades, cinnamic acid derivatives including natural, semi-synthetic and synthetic compounds had been proven to have a variety of pharmacological activities, 13) such as anticancer, 14,15) antimicrobial, [16][17][18] antioxidative, 18) anti-inflammatory, 15,[19][20][21] anti-Mycobactrium tuberculosis, [22][23][24] antiviral, 25) anti-human immunodeficiency virus (HIV), [26][27][28] antidiabetic, 29) anticholesterolemic, 30) analgesic, 31) hepatoprotective, 32,33) immunoprotective, 34) inducing neural progenitor cell proliferation 35) and anxiolytic activity. 36) Especially, what interests us is that cinnamic acid derivatives also have significant antiparasitic activities on plasmodia, 37) Leishmania 38) and nematode.…”

Two cinnamoyloctopamine antioxidants from garlic skin attenuates oxidative stress and liver pathology in rats with non-alcoholic steatohepatitis

“…1) were identified as the primary antioxidant constituents of garlic skin (Ichikawa et al 2003). Phenylpropanoid amides have shown a variety of pharmacologic properties (Fu et al 2010;Kart et al 2009). However, little is known about the properties of the two amides.…”