1338240-99-5Relevant articles and documents
Design, Synthesis, and Cytotoxicity of Novel 3-Arylidenones Derived from Alicyclic Ketones
Satam, Vijay,Bandi, Ravi K.,Behera, Ajaya K.,Mishra, Bijay K.,Tzou, Samuel,Brockway, Olivia,Babu, Balaji,Zeller, Matthias,Westbrook, Cara,Mooberry, Susan L.,Lee, Moses,Pati, Hari
, p. 700 - 708 (2012/04/04)
Forty-four novel chalcone-inspired analogs having a 3-aryl-2-propenoyl moiety derived from alicyclic ketones were designed, synthesized, and investigated for cytotoxicity against murine B16 and L1210 cancer cell lines. The analogs belong to four structurally divergent series, three of which (series g, h, and i) contain differently substituted cyclopentanone units and the fourth (series j) contains a 3,3-dimethyl-4-piperidinone moiety. Of these, the analogs in series j showed potential cytotoxic activity against murine B16 (melanoma) and L1210 (lymphoma) cells. The most active compounds 5j, 11j, 15j, and 12h produced IC50 values from 4.4 to 15μm against both cell lines. A single-crystal X-ray structure analysis and molecular modeling studies confirmed that these chalcones have an E-geometry about the alkene bond and possess a slightly 'twisted' conformation similar to that of combretastatin A-4. At a concentration of 30μm, compounds 5j, 11j, and 15j did not cause microtubule depolymerization in cells, suggesting that they have a different mechanism of action. Forty-four novel chalcone-inspired analogs were designed and synthesized. Several compounds gave IC50 values 4.4-15μm against the growth of L1210 and B16 murine cancer cells.