Exploring a cascade Heck-Suzuki reaction based route to kinase inhibitors using design of experiments

Ekebergh, Andreas, 1984 (author): Chalmers tekniska högskola,Chalmers University of Technology

Lingblom, Christine, 1984 (author): Gothenburg University,Göteborgs universitet,Institutionen för biomedicin, avdelningen för infektionssjukdomar,Institute of Biomedicine, Department of Infectious Medicine,University of Gothenburg

Sandin, Peter, 1977 (author): Chalmers tekniska högskola,Chalmers University of Technology

Wennerås, Christine, 1963 (author): Gothenburg University,Göteborgs universitet,Institutionen för biomedicin, avdelningen för infektionssjukdomar,Institute of Biomedicine, Department of Infectious Medicine,University of Gothenburg

Mårtensson, Jerker, 1965 (author): Chalmers tekniska högskola,Chalmers University of Technology

(creator_code:org_t)

2015
2015
English.
In: Organic and biomolecular chemistry. - : Royal Society of Chemistry (RSC). - 1477-0520 .- 1477-0539. ; 13:11, s. 3382-3392

Related links:: http://dx.doi.org/10...; show more...; https://gup.ub.gu.se...; https://doi.org/10.1...; https://research.cha...; show less...

Abstract Subject headings

Design of Experiments (DoE) has been used to optimize a diversity oriented palladium catalyzed cascade Heck-Suzuki reaction for the construction of 3-alkenyl substituted cyclopenta[b]indole compounds. The obtained DoE model revealed a reaction highly dependent on the ligand. Guided by the model, an optimal ligand was chosen that selectively delivered the desired products in high yields. The conditions were applicable with a variety of boronic acids and were used to synthesize a library of 3-alkenyl derivatized compounds. Focusing on inhibition of kinases relevant for combating melanoma, the library was used in an initial structure-activity survey. In line with the observed kinase inhibition, cellular studies revealed one of the more promising derivatives to inhibit cell proliferation via an apoptotic mechanism.

By the author/editor: Ekebergh, Andrea ...; Lingblom, Christ ...; Sandin, Peter, 1 ...; Wennerås, Christ ...; Mårtensson, Jerk ...

About the subject

By the university: University of Gothenburg; Chalmers University of Technology

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