Search

A series of substituted rutaecarpines were prepared by employing Fischer indole synthesis as key step and their inhibitory activities on COX-1 and 2 as well as selectivity on COX-2 were evaluated. The compounds with a methanesulfonyl and a bromo group at C10 showed promising inhibitory activity (IC 5 0 = 0.27, 0.35 μM, respectively) with selectivity.

One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl(2) is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

A series of rutaecarpine derivatives were prepared by employing previously reported methods and their inhibitory activities against topoisomerase I and II were evaluated. Among them, strongly cytotoxic 10-bromorutaecarpine and 3-chlororutaecarpine showed strong inhibitory activities against topo I and II.

One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl(2) is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl(2) is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

A series of new 3,2'-polymethylene-2-(quinol-2-yl)-4(3H)-quinazolinones and their aza-analogues were prepared as a homologous series of luotonin A. Their inhibitory activities against topoisomerase and cytotoxicities against selected cancer cell lines were evaluated to show that luotonin A and its aza-analogue were shown significant cytotoxicity. Conformational study revealed that trimethylene-bridged systems were rigid at room temperature with activation energies for interconversion of 15.7 and 14.6 kcal/mol for 3,2'-trimethylene-2-(quinol-2-yl)-4(3H)-quinazolinone and its aza-anlogue, respectively.

Homologous series of rutaecarpine were prepared by structurally modifying the C-ring and were evaluated their inhibitory activities on COX-2. The inhibitory activity on COX-2 increased with the increase of methylene unit while the selectivity on COX-2 over COX-1 decreased to lead a loss in trimethylene bridged system.