1379669-18-7

Upstream product

• 41979-39-9 4-piperidone hydrochloride 
• 459-57-4 4-fluorobenzaldehyde 

Downstream Products

• 330450-40-3 3,5-bis(4-fluorobenzylidene)-4-oxopiperidine 

Relevant academic research and scientific papers

Synthesis and antimicrobial activity of new 3,5-diarylidene-4-piperidone derivatives

Three series of heteroaromatic analogues (twenty seven compounds) with monoketone linkers were synthesized and evaluated for their antimicrobial activity against six microbial strains. Among them, 3,5-dibenzylidene-1-[(3,5-dichloro-2-hydroxyphenyl)sulfonyl]piperidin-4-one (5e) showed the best antifungal activity against Aspergillus niger and A. fumigatus. Structural elucidation of the synthesized compounds was realised based on various spectroscopic methods.

CLEFMA - An anti-proliferative curcuminoid from structure-activity relationship studies on 3,5-bis(benzylidene)-4-piperidones

3,5-Bis(benzylidene)-4-piperidones are being advanced as synthetic analogs of curcumin for anti-cancer and anti-inflammatory properties. We performed structure-activity relationship studies, by testing several synthesized 3,5-bis(benzylidene)-4-piperidones for anti-proliferative activity in lung adenocarcinoma H441 cells. Compared to the lead compound 1, or 3,5-bis(2-fluorobenzylidene)-4-piperidone, five compounds were found to be more potent (IC50 50 >50 μM). Based on the observations, we synthesized 4-[3,5-bis(2-chlorobenzylidene-4-oxo-piperidine-1-yl)-4-oxo-2- butenoic acid] (29 or CLEFMA) as a novel analog of 1. CLEFMA was evaluated for anti-proliferative activity in H441 cells, and was found to be several folds more potent than compound 1. We did not find apoptotic cell population in flow cytometry, and the absence of apoptosis was confirmed by the lack of caspase cleavage. The electron microscopy of H441cells indicated that CLEFMA and compound 1 induce autophagic cell death that was inhibited by specific autophagy inhibitor 3-methyladenine. The results suggest that the potent and novel curcuminoid, CLEFMA, offers an alternative mode of cell death in apoptosis-resistant cancers.