92520-33-7Relevant academic research and scientific papers
Synthesis, antitumor activity evaluation of some new N-aroyl-α, β-unsaturated piperidones with fluorescence
Sun, Jufeng,Wang, Suwen,Li, Hongjuan,Jiang, Wenguo,Hou, Guige,Zhao, Feng,Cong, Wei
, p. 495 - 502 (2016)
Novel N-aroyl-α,β-unsaturated piperidones, series 1, series 2 and series 3 (featuring 2-bromo-4,5-dimethoxybenzylidene, 4-dimethylaminobenzylidene and 4-trifluoromethylbenzylidene, respectively), were synthesized as candidate cytotoxins. Most of the compo
Structure activity relationship analysis of antiproliferative cyclic C5-curcuminoids without DNA binding: Design, synthesis, lipophilicity and biological activity
Huber, Imre,Rozmer, Zsuzsanna,Gy?ngyi, Zoltán,Budán, Ferenc,Horváth, Péter,Kiss, Eszter,Perjési, Pál
, (2020/01/21)
The chemical susceptibility of the β-diketone linker between the two aromatic rings in the structure of curcumin to hydrolysis and metabolism has made it crucial to investigate structurally modified analogs of curcumin without such shortcomings. The synth
Novel conjugated unsaturated ketones with submicromolar potencies towards some leukemic and colon cancer cells
Balzarini, Jan,Das, Swagatika,Das, Umashankar,Dimmock, Jonathan R.,Dimmock, Stephen G.,Inci Gul, H.
, p. 430 - 438 (2019/07/12)
Background: Cancer continues to be the major health burden worldwide. There is an urgent need for the development of novel antineoplastic compounds to treat this devastating condition. Various alkylating anticancer drugs have been employed in the clinic for treating cancers. Unsaturated conjugated ketones are a group of alkylators which are of significant interest as potent antineoplastic agents. Objective: The goal of this study is to discover unsaturated conjugated ketones which are novel potent cytotoxins displaying growth-inhibitory properties towards neoplasms and also to serve as cytotoxic warheads in drug development. Methods: A variety of 3,5-bis (benzylidene)-4-piperidones 2a-n were synthesized and evaluated against a number of neoplastic cell lines. The short-term neurotoxicity of 2a-k, n was evaluated in mice by i.p. administration using doses level of 30, 100 and 300 mg/kg. Statistical correlations for determining structure-activity relationships were performed using an SPSS software. Results: A number of compounds display cytotoxic potencies in the region of 10-7 to 10-8 M and some of the structural features contributing to the cytotoxicity were identified. Compounds 2a-d, 2h demonstrated substantially higher cytotoxic potencies compared to melphalan and 5- fluorouracil against a panel of leukemic and colon cancer cell lines. These lead cytotoxins comply with drug-likeness properties. In general, the antineoplastics 2 are well tolerated in mice using a short-term neurotoxicity screening. Conclusion: In general, this group of compounds comprises excellent cytotoxic agents, which warrant their further development as cytotoxic warheads.
Piperidone centered curcumin analogues with double chalcone skeleton structures and derivatives and application of curcumin analogues
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Paragraph 0058; 0059; 0060; 0062, (2018/04/03)
The invention discloses Piperidone centered curcumin analogues with double chalcone skeleton structures and derivatives and application of curcumin analogues. The curcumin analogues and the derivatives keep high target spot combination activity, can be used for combination and imaging of amyloid plaques (such as senile plaques) and are expectedly applied to early diagnosis, evaluation, preventionand treatment of amyloid protein aggregation or deposition diseases such as Alzheimer's disease. The compounds contain polyfluoro in molecular structure and are especially applicable to amyloid protein MRI (magnetic resonance imaging) imaging molecular probes to provide a foundation for early diagnosis of Alzheimer's disease.
Novel 3,5-bis(arylidene)-4-piperidone dimers: Potent cytotoxins against colon cancer cells
Das, Swagatika,Das, Umashankar,Michel, Deborah,Gorecki, Dennis K.J.,Dimmock, Jonathan R.
, p. 321 - 328 (2013/07/11)
Two novel series of dimeric 3,5-bis(arylidene)-4-piperidones 7 and 8 were prepared as cytotoxic agents. A specific objective of this study was the discovery of novel compounds displaying potent anti-proliferative activities against colon cancers. Most of
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.
