1108622-06-5Relevant academic research and scientific papers
A Suzuki cross-coupling and intramolecular aza-Michael addition reaction sequence towards the synthesis of 1,10b-epi-7-deoxypancratistatins and their cytotoxicity studies
Pandey, Ganesh,Balakrishnan, Madhesan,Swaroop, Pandrangi Siva
experimental part, p. 5839 - 5847 (2009/06/08)
The development of an efficient approach to the construction of a phenanthridone is described. The convergent strategy commences with the preparation of Suzuki cross-coupling reaction precursors, arylboronic acid 12 and α-iodo enone 19, from piperonylamine (9) and (-)-D-quinic acid (10), respectively. The coupling of 12 and 19 followed by a key intramolecular aza-Michael addition produced phenanthridone 21 featuring a cis-fused B-C ring junction. The syntheses of compounds 25 and 26, both of which are C-1 and C-10b epimers of the naturally occurring potent antitumor agent 7-deoxypancratistatin (2), from 21 are elaborated in detail in this paper. The cytotoxicities of 25 and 26 were evaluated against three different cancer cell lines. Compound 26 served as a moderate growth inhibitor of THP-1 monocytic cells (GI50 = 14.5 μg/mL). Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
