74746-12-6Relevant academic research and scientific papers
Efficient Synthesis of Glaziovianin A Isoflavone Series from Dill and Parsley Extracts and Their in Vitro/in Vivo Antimitotic Activity
Semenov, Victor V.,Tsyganov, Dmitry V.,Semenova, Marina N.,Chuprov-Netochin, Roman N.,Raihstat, Mikhail M.,Konyushkin, Leonid D.,Volynchuk, Polina B.,Marusich, Elena I.,Nazarenko, Vera V.,Leonov, Sergey V.,Kiselyov, Alex S.
, p. 1429 - 1438 (2016)
A concise six-step protocol for the synthesis of isoflavone glaziovianin A (GVA) and its alkoxyphenyl derivatives 9 starting with readily available plant metabolites from dill and parsley seeds was developed. The reaction sequence involved an efficient conversion of the key intermediate epoxides 7 into the respective β-ketoaldehydes 8 followed by their Cu(I)-mediated cyclization into the target series 9. The biological activity of GVA and its derivatives was evaluated using a panel of seven human cancer cell lines and an in vivo sea urchin embryo assay. Both screening platforms confirmed the antimitotic effect of the parent GVA (9cg) and its alkoxy derivatives. Structure-activity relationship studies suggested that compounds 9cd and 9cf substituted with trimethoxy- and dillapiol-derived B-rings, respectively, were less active than the parent 9cg. Of the evaluated human cancer cell lines, the A375 melanoma cell line was the most sensitive to the tested molecules. Notably, the target compounds were not cytotoxic against human peripheral blood mononuclear cells up to 10 μM concentration. Phenotypic readouts from the sea urchin assay unequivocally suggest a direct microtubule-destabilizing effect of isoflavones 9cg, 9cd, and 9cf.
Beyond the Corey–Chaykovsky Reaction: Synthesis of Unusual Cyclopropanoids via Desymmetrization and Thereof
Patel, Kaushalendra,Mishra, Uttam K.,Mukhopadhyay, Dipto,Ramasastry
supporting information, p. 4568 - 4571 (2019/11/03)
Desymmetrization-based protocols for the synthesis of highly functionalized indeno-spirocyclopropanes and cyclopropa-fused indanes have been established through unexpected reactions triggered by the Corey–Chaykovsky reagent. These structures were further elaborated in one step to privileged scaffolds such as fluorenones, indenones, and naphthaphenones. For instance, an acid-catalyzed transformation of indeno-spirocyclopropanes provided fluorenones via a homo-Nazarov-type cyclization, and naphthaphenones were obtained via an acid-catalyzed cyclopropane ring-opening/retro-Michael sequence.
Electrocyclic Reactions of Protonated Chalcones: Synthesis of 3-Arylindan-1-ones
McDonald, Edward,Smith, Paul
, p. 837 - 842 (2007/10/02)
A series of ortho-bromochalcones has been prepared and each has been heated and irradiated in strong acid.In most cases a four-electron electrocyclic reaction occurred preferentially to give 3-arylindan-1-ones in good yield.The acrylchalcone 4'-methoxy-3,
