Catalytic asymmetric dearomative [4 + 2] annulation of 2-nitrobenzofurans and 5 <i>H</i>-thiazol-4-ones: stereoselective construction of dihydrobenzofuran-bridged polycyclic skeletons

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Abstract

An organocatalytic asymmetric dearomative [4 + 2] annulation of 2-nitrobenzofurans and 5 H-thiazol-4-ones is developed for the construction of dihydrobenzofuran-bridged polycyclic skeletons with good results.

Abstract

An organocatalytic asymmetric dearomative [4 + 2] annulation of 2-nitrobenzofurans and 5 H-thiazol-4-ones is described for the first time. With a chiral dipeptide-based squaramide as the catalyst, a series of dihydrobenzofuran-bridged polycyclic compounds bearing four contiguous stereocenters including three quaternary stereogenic centers were obtained with excellent diastereoselectivities and high enantioselectivities under mild conditions. Preliminary biological evaluation indicated that the products exhibit impressive cytotoxicity against the human cancer cell lines A549 and K562.

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Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays

Tim R. Mosmann (1983)

A tetrazolium salt has been used to develop a quantitative colorimetric assay for mammalian cell survival and proliferation. The assay detects living, but not dead cells and the signal generated is dependent on the degree of activation of the cells. This method can therefore be used to measure cytotoxicity, proliferation or activation. The results can be read on a multiwell scanning spectrophotometer (ELISA reader) and show a high degree of precision. No washing steps are used in the assay. The main advantages of the colorimetric assay are its rapidity and precision, and the lack of any radioisotope. We have used the assay to measure proliferative lymphokines, mitogen stimulations and complement-mediated lysis.

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Catalytic Asymmetric Dearomatization Reactions

Chun-Xiang Zhuo, Wei Zhang, Shu-Li You (2012)

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Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry.

Minghao Feng, Bingqing Tang, Steven Liang … (2016)

The impact of the development of sulfur therapeutics is instrumental to the evolution of the pharmaceutical industry. Sulfur-derived functional groups can be found in a broad range of pharmaceuticals and natural products. For centuries, sulfur continues to maintain its status as the dominating heteroatom integrated into a set of 362 sulfur-containing FDA approved drugs (besides oxygen or nitrogen) through the present. Sulfonamides, thioethers, sulfones and Penicillin are the most common scaffolds in sulfur containing drugs, which are well studied both on synthesis and application during the past decades. In this review, these four moieties in pharmaceuticals and recent advances in the synthesis of the corresponding core scaffolds are presented.