71089-18-4Relevant academic research and scientific papers
An amino-benzosuberene analogue that inhibits tubulin assembly and demonstrates remarkable cytotoxicity
Tanpure, Rajendra P.,George, Clinton S.,Sriram, Madhavi,Strecker, Tracy E.,Tidmore, Justin K.,Hamel, Ernest,Charlton-Sevcik, Amanda K.,Chaplin, David J.,Trawick, Mary Lynn,Pinney, Kevin G.
, p. 720 - 724 (2013/11/06)
The recent discovery of a small-molecule benzosuberene-based phenol that demonstrates remarkable picomolar cytotoxicity against selected human cancer cell lines and strongly inhibits tubulin polymerization (1-2 μM) inspired the design and synthesis of a variety of new, structurally diverse benzosuberene derivatives. An efficient synthetic route to functionalized benzosuberenes was developed. This methodology utilized a Wittig reaction, followed by a selective alkene reduction and ring-closing cyclization to form the core benzosuberone structure. This synthetic route facilitated the preparation of a 4-nitro-1-(3′,4′,5′-trimethoxyphenyl) benzosuberene derivative and its corresponding 4-amino analogue in good yield. The 4-amino analogue was a strong inhibitor of tubulin polymerization (1.2 μM), demonstrated enhanced cytotoxicity against the human cancer cell lines examined (GI50 = 33 pM against SK-OV-3 ovarian cancer, for example), and exhibited a concentration dependent disruption of a pre-established capillary-like network of tubules formed from human umbilical vein endothelial cells.
Efficient Method for Preparing Functionalized Benzosuberenes
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, (2012/06/01)
The disclosed process can efficiently synthesize functionalized benzosuberenes. The process provides an improved method of production of benzosuberene and compounds containing a benzosuberene moiety, which is characterized by a ring closing methodology comprising reaction of a 5-phenylpentanoic acid with Eaton's reagent to form the benzosuberone. The process, optionally, further includes steps for adding a functional group at the ketone position.
