- Design and synthesis of Pictet-Spengler condensation products that exhibit oncogenic-RAS synthetic lethality and induce non-apoptotic cell death
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A series of Pictet-Spengler condensation derivatives (tetrahydro-β- carbolines) was designed, synthesized and evaluated for lethality against a panel of seven cancer cell lines. Seven compounds (2a, 13, 20, 21, 27, 29 and 34) showed lethality in at least five cell lines. Among these, compound 27 showed a unique selectivity towards oncogenic-RAS expressing BJ-TERT/LT/ST/RASV12 tumor cells, compared to non-transformed BJ-TERT cells. Further investigation revealed that 27 induces cell death without activation of caspases. This represents a useful new probe of non-apoptotic cell death and oncogenic-RAS synthetic lethality.
- Skouta, Rachid,Hayano, Miki,Shimada, Kenichi,Stockwell, Brent R.
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scheme or table
p. 5707 - 5713
(2012/10/07)
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- A ring closing metathesis approach to the indole alkaloid mitralactonine
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An efficient utilisation of RCM leading to a convenient synthesis of a pentacyclic indole alkaloid is described.
- Chavan, Subhash P.,Sharma, Pallavi,Sivappa,Kalkote, Uttam R.
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p. 9301 - 9303
(2007/10/03)
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- Synthesis of ajmalicine derivatives using Wittig-Horner and Knoevenagel reactions
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2-(2,3,4,9-Tetrahydro-1H-β-carbolin-1-yl)acetaldehyde, synthesized from tryptamine in five steps, is easily homologated by Wittig-Horner or Knoevenagel reactions to substituted acrylates. These highly reactive compounds are key intermediates in the synthesis of analogs of the natural indol alkaloid ajmalicine.
- Boumendjel, Ahcene,Nuzillard, Jean-Marc,Massiot, Georges
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p. 9033 - 9036
(2007/10/03)
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