75792-35-7Relevant articles and documents
BENZOSUBERENE ANALOGUES AND RELATED COMPOUNDS WITH ACTIVITY AS ANTICANCER AGENTS
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Paragraph 0098, (2020/03/01)
A series of benzosuberene analogues demonstrate effective inhibition of tubulin polymerization, cytotoxicity against human cancer cell lines, and vascular disruption in tumors.
Efficient synthetic methodology for the construction of dihydronaphthalene and benzosuberene molecular frameworks
Mondal, Deboprosad,Niu, Haichan,Pinney, Kevin G.
supporting information, p. 397 - 401 (2019/01/05)
Benzosuberene analogues (1 and 2) and dihydronaphthalene analogues (3 and 4) function as potent inhibitors of tubulin polymerization, demonstrate pronounced cytotoxicity (low nM to pM range) against human cancer cell lines, and are promising vascular disrupting agents (VDAs). As such, these compounds represent lead anticancer agents with potential translatability towards the clinic. Methodology previously established by us (and others) facilitated synthetic access to a variety of structural and functional group modifications necessary to explore structure activity relationship considerations directed towards the development of these (and related) molecules as potential therapeutic agents. During the course of these studies it became apparent that the availability of synthetic methodology to facilitate direct conversion of the phenolic-based compounds to their corresponding aniline congeners would be beneficial. Accordingly, modified synthetic routes toward these target phenols (benzosuberene 1 and dihydronaphthalene 3) were developed in order to improve scalability and overall yield [45-57% (1) and 32% (3)]. Moreover, benzosuberene-based phenolic analogue 1 and separately dihydronaphthalene-based phenolic analogue 3 were successfully converted into their corresponding aniline analogues 2 and 4 in good yield (>60% over three steps) using a palladium catalyzed amination reaction.
A synthetic BNC105 method
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Paragraph 0039; 0040; 0041, (2017/08/25)
The invention relates to a method for compounding BNC 105, which uses o-vanillin and 3,4,5- trimethoxy-benzaldehyde as starting materials. The o-vanillin is subjected to hydroxy protection and aldehyde oxidation to be hydrolyzed into phenol, and the pheno