145888-79-5Relevant articles and documents
α,β-unsaturated carbonyl system of chalcone-based derivatives is responsible for broad inhibition of proteasomal activity and preferential killing of human papilloma virus (HPV) positive cervical cancer cells
Bazzaro, Martina,Anchoori, Ravi K.,Mudiam, Mohana Krishna R.,Issaenko, Olga,Kumar, Srinivas,Karanam, Balasubramanyam,Lin, Zhenhua,Isaksson Vogel, Rachel,Gavioli, Riccardo,Destro, Federica,Ferretti, Valeria,Roden, Richard B. S.,Khan, Saeed R.
, p. 449 - 456 (2011)
Proteasome inhibitors have potential for the treatment of cervical cancer. We describe the synthesis and biological characterization of a new series of 1,3-diphenylpropen-1-one (chalcone) based derivatives lacking the boronic acid moieties of the previously reported chalcone-based proteasome inhibitor 3,5-bis(4-boronic acid benzylidene)-1-methylpiperidin-4-one and bearing a variety of amino acid substitutions on the amino group of the 4-piperidone. Our lead compound 2 (RA-1) inhibits proteasomal activity and has improved dose-dependent antiproliferative and proapoptotic properties in cervical cancer cells containing human papillomavirus. Further, it induces synergistic killing of cervical cancer cell lines when tested in combination with an FDA approved proteasome inhibitor. Exploration of the potential mechanism of proteasomal inhibition by our lead compound using in silico docking studies suggests that the carbonyl group of its oxopiperidine moiety is susceptible to nucleophilic attack by the γ-hydroxythreonine side chain within the catalytic sites of the proteasome.
Design, synthesis and tumour-selective toxicity of novel 1-[3-{3,5-bis(Benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone oximes and related quaternary ammonium salts
Aguilera, Renato J.,Amano, Shigeru,Balderrama, Karol S.,Contreras, Lisett,Das, Umashankar,Dimmock, Jonathan R.,Roayapalley, Praveen K.,Sakagami, Hiroshi,Sharma, Rajendra K.
, (2021/12/09)
A novel series of 1-[3-{3,5-bis(benzylidene)-4-oxo-1-piperidino}-3-oxopropyl]-4-piperidone oximes 3a–h and related quaternary ammonium salts 4a–h were prepared as candidate antineoplastic agents. Evaluation against neoplastic Ca9-22, HSC-2 and HSC-4 cells
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
