157977-26-9Relevant academic research and scientific papers
Synthesis of pyrrolidin-2-ones and of staurosporine aglycon (K-252c) by intermolecular Michael reaction
Mahboobi, Siavosh,Eibler, Ernst,Koller, Markus,Kumar KC, Sunil,Popp, Alfred,Schollmeyer, Dieter
, p. 4697 - 4704 (2007/10/03)
Indolo[2,3-a]pyrrolo[3,4-c]carbazoles were isolated from nature, e.g., from low plants, especially fungi, as structurally rare natural substances. Responsible for naming and also the most important representative of this type is staurosporine (1), isolated from Streptomyces staurosporeus, and its aglycon (2), also known as staurosporinone or K-252c. 3,4-Disubstituted pyrrolidin-2-ones, a group of compounds with many interesting biological properties are related to staurosporinone. The most important property is the inhibition of protein kinase C (PKC), so that this antiproliferative agent can interfere with the cell cycle. The synthetic strategy, developed by us, allows the synthesis of pyrrolidin-2-ones by an intermolecular Michael addition, starting from nitroethene derivatives and substituted acetate Michael donors. With this method also enantioselective syntheses can be carried out using chiral auxiliaries. After reduction of the nitro group and subsequent lactamization, the lactam partial structure, which is essential for the biological activity, is obtained. Besides indole substituents, which were used for the synthesis of staurosporinone, substituted indole-, phenyl- , and pyridyl- as well as enantiomerically pure (S)-proline derivatives were used. Here, considerably high diastereoselectivity and enantioselectivity ((S)-pyrrolidine) could be detected. Just like the total synthesis of staurosporinone within three steps, the easiest and shortest approach reported up to now, with good to moderate yields, this sequence allows highly diastereoselective syntheses, which open the easy access to a new family of compounds.
1,3-Dinitropropanes: Intermediates to 1,3-diaminopropanes
Mahboobi,Grothus
, p. 349 - 358 (2007/10/02)
Reduction of malodinitriles 4 and 10 to the corresponding diamines does not work. - Reduction of dinitro-2-(indol-3-yl)-propanes 13 and 16 and subsequent reaction with K2PtCl4 afford the corresponding dichloroplatinum(II) complexes 14 and 17. Complexes 17 show weak binding affinities to the estrogen receptor and no antitumor activity towards MCF-7 and MDA-MB-2231-cell lines. - Twofold addition of nitromethane to aldehyde 24 is possible.
3-Substituted 2-phenylindoles: Synthesis and biological properties
Mahboobi,Grothus,Von Angerer
, p. 481 - 492 (2007/10/02)
Knoevenagel-reaction of indol-3-carbaldehydes 5a,b and 7a,b with nitromethane leads to the nitroethenes 12 and 14, the analogous reaction with malodinitrile to the methylidenemalonic acid dinitriles 16.- Michael-addition of nitromethane at 12 and 14 affor
