Carbophilic 3-component cascades

Access to complex bioactive cyclopropyl diindolylmethanes

Nigel M. Groome, Elghareeb E. Elboray, Martyn W. Inman, H. Ali Dondas, Roger M. Phillips, Colin Kilner, Ronald Grigg

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Naturally occurring indole-3-carbinol and 3,3-diindolylmethane show bioactivity in a number of disparate disease areas, including cancer, prompting substantial synthetic analogue activity. We describe a new approach to highly functionalised derivatives that starts from allene gas and proceeds via the combination of a three-component Pd0-catalysed cascade with a one-pot, three-component carbophilic PtII cascade linked to a stereoselective acid-catalysed Mannich-Michael reaction that generates complex cyclopropyl diindolylmethanes which show selective activity against prostate cancer cell lines.

Original languageEnglish
Pages (from-to)2180-2184
Number of pages5
JournalChemistry - A European Journal
Volume19
Issue number6
Early online date20 Dec 2012
DOIs
Publication statusPublished - 4 Feb 2013
Externally publishedYes

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Bioactivity
Cells
Derivatives
Acids
Gases
diindolylmethane
indole-3-carbinol
propadiene

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Groome, Nigel M. ; Elboray, Elghareeb E. ; Inman, Martyn W. ; Dondas, H. Ali ; Phillips, Roger M. ; Kilner, Colin ; Grigg, Ronald. / Carbophilic 3-component cascades : Access to complex bioactive cyclopropyl diindolylmethanes. In: Chemistry - A European Journal. 2013 ; Vol. 19, No. 6. pp. 2180-2184.
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Carbophilic 3-component cascades : Access to complex bioactive cyclopropyl diindolylmethanes. / Groome, Nigel M.; Elboray, Elghareeb E.; Inman, Martyn W.; Dondas, H. Ali; Phillips, Roger M.; Kilner, Colin; Grigg, Ronald.

In: Chemistry - A European Journal, Vol. 19, No. 6, 04.02.2013, p. 2180-2184.

Research output: Contribution to journalArticle

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T1 - Carbophilic 3-component cascades

T2 - Access to complex bioactive cyclopropyl diindolylmethanes

AU - Groome, Nigel M.

AU - Elboray, Elghareeb E.

AU - Inman, Martyn W.

AU - Dondas, H. Ali

AU - Phillips, Roger M.

AU - Kilner, Colin

AU - Grigg, Ronald

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KW - diindolylmethanes

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