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New Tricks for an Old Dog (II): Applications of 2-Acetylphenol in Bioactivity-Oriented Organic Synthesis
Update time: 2014-11-03
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YANG Chunhao’s group from Shanghai Institute of Materia Medica is mainly focus on the discovery of novel anti-cancer drugs and also interesting in the methodologies of bioactivity-oriented synthesis of novel heterocycles to provide a larger array of the chemical space in drug discovery. They have developed lots of new synthetic approaches (New Tricks) to construct high-quality libraries directly from readily accessible and simple starting materials (Old Dog) under mild and green conditions.

Compounds bearing the trifluoromethylthio (SCF3) group have been found in many pharmaceuticals, agrochemicals and materials because of their hydrophobicity and desirable   electronegativity. Chromone and its derivatives, which are found in many natural products and pharmaceuticals with a wide range of physiological and biological activities, are greatly versatile building blocks for constructing various heterocycles.

Consequently, introduction of SCF3 group to chromones might be very desirable and result in further advances in the pharmacological applications. Recently, Yang and co-workers first demonstrated a facile and general synthetic route to a range of 3-((trifluoromethyl)thio) chromones via in situ generation of electrophilic trifluoromethylthio species from trichloroisocyanuric acid (TCCA) and AgSCF3 on Organic Letters.  

This practical and easily handled reaction, which was insensitive to air and moisture, could occur under mild conditions in a short reaction time without any extra additives. Moreover, the reaction could be scaled-up easily. Additionally, this approach could be applied in construction of (trifluoromethyl)thio-containing analogue of natural topopyrone C.The link to the article: http://pubs.acs.org/doi/abs/10.1021/ol502751k  

This work was financially supported by the Chinese Academy of Sciences (“Interdisciplinary Cooperation Team” Program for Science and Technology Innovation), the National Natural Science Foundation of China (81321092), and SKLDR/SIMM (SIMM1403ZZ-01).

In addition, Yang’s group did a lot of research on the application of 2-Acetylphenol, including the synthesis of a series of privileged structures in medicinal chemistry such as 2aminopyrroles/pyridinesOrg. Lett.,2014164186)、α-carbolinesOrg. Biomol. Chem.,201412355)、pyridinefused coumarinsRSC. Adv.,201335807)、2-substituted pyrrolo[2,1-f][1,2,4]triazin-4(3H)-onesRSC. Adv. 2013335807)、pyrazole-containing bisphosphonate estersOrg. Biomol. Chem.,2012107730etc. What’s more, cooperating with Miao’s group, they found two (YCH337 and YCH665) of those compounds could inhibit both tubulin and topoisomerase II at very low (nanomolar) concentration and further studies of this series of compounds are in progress.

 

 
 
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