104169-80-4Relevant articles and documents
Synthesis and antiproliferative activity of cyclic arylidene ketones: a direct comparison of monobenzylidene and dibenzylidene derivatives
Huber, Imre,Zupk, Istvn,Kovcs, Ida J.,Minorics, Renta,Gulys-Fekete, Gergely,Masz, Gbor,Perjsi, Pl
, p. 973 - 981 (2015)
Abstract To give further insight into the influence of the structural modifications of enones and dienones on their antiproliferative properties, 25 derivatives of enones: (E)-2-benzylidene-1-cyclohexanones, (E)-2-benzylidene-1-tetralones, (E)-2-benzylidene-1-indanone, and dienones: (E,E)-2,5- or 2,6-dibenzylidene-1-cyclanones, (E,E)-3,5-dibenzylidene-4-piperidones were synthesized using a newly developed "one-pot" synthetic method. Due to the fact that all of them have the same aryl substituents (phenyl or 4-chlorophenyl) in the arylidene moiety, it is possible to compare the relevant contribution of the single-point structural modifications (type of ring or N-substitution) on their potency on the basis of their IC 50 values. Their antiproliferative activity was evaluated against the following four human adherent cancer cell lines: HeLa, A431, A2780, and MCF7. The cytotoxicity screen has revealed that the dibenzylidene dienones in general dominate the monobenzylidene enones in this respect. The nitrogen-containing heterocyclic dienones at the same time displayed higher inhibitory properties toward these human carcinoma cell lines compared with their homocyclic dienone analogs. One of the eight newly prepared 4-piperidone derivatives, N-(γ-oxobutyl)-(E,E)-3,5-bis(p-chlorobenzylidene)-4-piperidone is as potent a cell growth inhibitor (IC 50 of 0.438-1.409 μM) as the N-methyl-(E,E)-3,5-bis(p-chlorobenzylidene)-4-piperidone (IC 50 of 0.447-1.048 μM), one of the most active among the previously described compounds in this series. Catalytic hydrogen-transfer isomerization of compounds with two exocyclic benzylidene double bonds to derivatives with endocyclic double bonds results in the complete loss of antiproliferative activity. The structural modifications and 50 % inhibitory concentration (IC 50) values resulted in correlations which can promote the design of more potent derivatives of the 4-piperidone dienones.
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
Microwave accelerated facile and efficient synthesis of piperido[3′,4′:5,6]pyrano[2,3-d] pyrimidinones catalyzed by basic ionic liquid [BMIM]OH
Siddiqui,Srivastava, Arjita,Shamim, Shayna,Srivastava, Anjali,Waseem, Malik A.,Shireen,Rahila,Abumhdi, Afaf A.H.,Srivastava, Anushree,Rai, Pragati
, p. 126 - 135 (2014/01/06)
A basic ionic liquid [BMIM]OH could very efficiently catalyze the synthesis of piperido[3′,4′:5,6]pyrano[2,3-d]pyrimidinone derivatives from pyrano[3,2-c]piperidine analogues and carbonyl compounds. [BMIM]OH acted as a catalyst as well as the reaction medium and could be used for the reactions for five times without any appreciable loss of its catalytic efficiency. The synergic couple of microwave and ionic liquid provided high yields of the product in very short reaction times and allowed easy workup.
