Torquoselective Mechanochemical Activation of the Staudinger Reaction To Form β-Lactams
نویسندگان
چکیده
منابع مشابه
Asymmetric synthesis of anticancer β-lactams via Staudinger reaction.
This study describes the symmetric synthesis of novel β-lactams derived from chrysene directed towards their SAR, as well as their biological activities against several cancer cell lines in vitro. To our knowledge, this is the first report on the synthesis and biological evaluation of optically active anticancer β-lactams. That these anticancer effects are not uniform against all tumor lines su...
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Fifteen novel β-lactams bearing the N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2-aminoethyl) β-lactams 6a-o were synthesized by the ketene-imine [2+2] cycloaddition reaction (Staudinger ). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to the formation of the cis-β-lactam derivatives. These newly synthesized β-lactams were evaluated for the...
متن کاملDiastereoselective synthesis of potent antimalarial cis-β-lactam agents
Fifteen novel β-lactams bearing the N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2-aminoethyl) β-lactams 6a-o were synthesized by the ketene-imine [2+2] cycloaddition reaction (Staudinger ). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to the formation of the cis-β-lactam derivatives. These newly synthesized β-lactams were evaluated for the...
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A new transformation based on the Staudinger reaction is described, and its application in the design of a novel switch element to control peptide folding is demonstrated. We found that the azide switch is activated rapidly in water to promote acyl transfer using tris(2-carboxyethyl)phosphine hydrochloride (TCEP) via the Staudinger reaction. Our findings expand the repertoire of uses of the Sta...
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Pseudomonas aeruginosa is a relevant opportunistic pathogen particularly problematic due to its low intrinsic susceptibility to antibiotics. Intrinsic resistance has been traditionally attributed to the low permeability of cellular envelopes together with the presence of chromosomally-encoded detoxification systems such as multidrug efflux pumps or antibiotic inactivating enzymes. However, some...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2018
ISSN: 0022-3263,1520-6904
DOI: 10.1021/acs.joc.7b03036