193551-49-4Relevant academic research and scientific papers
Regioselective photo-oxidation of 1-benzyl-4,9-dihydro-3H-β-carbolines
Garcia, Marcos D.,Wilson, A. James,Emmerson, Daniel P. G.,Jenkins, Paul R.
, p. 2586 - 2588 (2008/03/31)
The synthesis of a series of β-carboline-based analogues of the natural product fascaplysin is presented; the compounds were produced using a novel photo-oxidation reaction of 1-benzyl-4,9-dihydro-3H-β-carbolines as the key step. The Royal Society of Chemistry 2006.
Synthesis, crystal structure and biological activity of β-carboline based selective CDK4-cyclin D1 inhibitors
Garcia, Marcos D.,Wilson, A. James,Emmerson, Daniel P.G.,Jenkins, Paul R.,Mahale, Sachin,Chaudhuri, Bhabatosh
, p. 4478 - 4484 (2008/09/19)
The design, synthesis and biological activity of a series of non-planar dihydro-β-carboline and β-carboline-based derivatives of the toxic anticancer agent fascaplysin is presented. We show these compounds to be selective inhibitors of CDK4 over CDK2 with an IC50 (CDK4-cyclin D1) = 11 mol for the best compound in the series 4d. The crystallographic analysis of some of the compounds synthesised (3b/d and 4a-d) was carried out, in an effort to estimate the structural similarities between the designed inhibitors and the model compound fascaplysin. The Royal Society of Chemistry.
A simple and practical approach to the synthesis of the marine sponge pigment fascaplysin and related compounds
Radchenko, Oleg S.,Novikov, Vyacheslav L.,Elyakov, George B.
, p. 5339 - 5342 (2007/10/03)
Fascaplysin 1, an antimicrobial and cytotoxic red pigment of the marine sponge Fascaphysinopsis sp., has been synthesized in five steps from tryptamine 2 in 44% overall yield. The key steps in the synthesis are: (a) dehydrogenation of the dihydro-β-carboline intermediate 4 simultaneously with its benzylic oxidation on treatment with MnO2 and (b) the thermal cyclization of the resulting β-carboline 7 into a quaternary salt 8. Similarly, indoloisoquinolines 15 and 16, the tetracyclic analogues of 1, were prepared in six steps from α-amino ketone 9 in 59 and 55% overall yields, respectively.
