1217237-15-4Relevant academic research and scientific papers
3. 5 - Aryl methylene - N - benzenesulfonyl -4 - piperidine compound and its preparation method (by machine translation)
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Paragraph 0031; 0033; 0053, (2018/07/30)
The invention relates to ten with anti-tumor and anti-inflammatory activity of 3, 5 - aryl methylene - N - benzenesulfonyl - 4 - piperidine compounds, which belongs to the anti-tumor and anti-inflammatory pharmaceutical technology field. The preparation method is first of all through the 4 - piperidone hydrochloride are respectively connected with the benzopyrone to claessen - Schmidt condensation reaction to obtain 3, 5 - aryl methylene - N - H - 4 - piperidone hydrochloride intermediate, and then with a sulfonylation reagent and generating benzene acylation reaction 3, 5 - aryl methylene - N - benzenesulfonyl - 4 - piperidine compounds. The compound anti-tumor and anti-inflammatory activity is good, can avoid the use of the anti-tumor gene is toxic, low toxicity to normal cells, while at the same time having anti-inflammatory activity. Preparation method is simple in operation, mild reaction conditions, high synthesis yield, benefit its anti-tumor and anti-inflammatory field of widely popularized. (by machine translation)
CLEFMA - An anti-proliferative curcuminoid from structure-activity relationship studies on 3,5-bis(benzylidene)-4-piperidones
Lagisetty, Pallavi,Vilekar, Prachi,Sahoo, Kaustuv,Anant, Shrikant,Awasthi, Vibhudutta
supporting information; experimental part, p. 6109 - 6120 (2010/09/15)
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.
