Synthesis, cytotoxicity, and structure–activity insight of NH- and N-methyl-3,5-bis-(arylidenyl)-4-piperidones

Synthesis and cholinesterase inhibitory activity studies of some piperidinone derivatives

“…The synthesis of 4-piperidinone derivatives were realized in a simple ''one-pot'' method (Scheme 2). [13][14][15][16] In the ''one-pot'' synthesis, 1-benzyl-4-piperidinone (5 mmol) and corresponding aromatic aldehyde (10 mmol) were dissolved in 30 mL of methanol at 0 °C (ice bath). To this reaction mixture, 30% solution of KOH (2 mL) was added dropwise.…”

N-benzyl-(3E,5E)-3,5-bis(2-hydroxybenzylidene)-4-piperidone

“…Analogous compounds to (E)-3,5-bis(benzylidene)-4-piperidones presented noteworthy cytotoxic activity against leukimia cell lines and colon cancer among others [11]. Different substituents with opposing electronic properties in the benzene rings were designed to investigate and discuss the structure-activity relationship [12]. During the course of our continuing search for novel curcumin analogues, we synthesized and characterized 3,4-bis(2-hydroxybenzylidene)-4-piperidone [13].…”

Crystal structures of 3,5-bis[(E)-3-hydroxybenzylidene]-1-methylpiperidin-4-one and 3,5-bis[(E)-2-chlorobenzylidene]-1-methylpiperidin-4-one

“…It has been shown to exhibit anti-oxidant (Rostom et al, 2009), anti-inflammatory (Suzuki et al, 2005), antiviral (Kumar et al, 2007) and antibacterial (Bandgar et al, 2012) activities, and thus has potential against various malignant cancers, diabetes, allergies, arthritis and other chronic illnesses (Yadav et al, 2010;Reddy et al, 2009;Aggarwal et al, 2003;Insuasty et al, 2013;Wu et al, 2013). For the purpose of finding new derivatives with increased systemic bioavailability and enhanced pharmacological activity (Zhao et al, 2010), chemical modifications as well as the synthesis of curcumin analogues have been attempted by many research groups in order to find a better treatment for various diseases (Siddiqui et al, 2006;Gregory et al, 2013). Analogous compounds to (E)-3,5-bis(benzylidene)-4-piperidones present noteworthy cytotoxic activity against leukemia cell lines and colon cancer, among others (Gregory et al, 2013).…”

“…For the purpose of finding new derivatives with increased systemic bioavailability and enhanced pharmacological activity (Zhao et al, 2010), chemical modifications as well as the synthesis of curcumin analogues have been attempted by many research groups in order to find a better treatment for various diseases (Siddiqui et al, 2006;Gregory et al, 2013). Analogous compounds to (E)-3,5-bis(benzylidene)-4-piperidones present noteworthy cytotoxic activity against leukemia cell lines and colon cancer, among others (Gregory et al, 2013). Different substituents were designed to investigate and discuss the structure-activity relationship (Insuasty et al, 2013).…”

“…Both compounds were synthesized according to a partially modified procedure of a previous report (Gregory et al, 2013).…”