Synthesis and Cytotoxic Activity of Pyranocoumarins of the Seselin and Xanthyletin Series

Abstract

The synthesis of known (3-6) and new (7-10 and 14-22) coumarins in the seselin and xanthyletin series is described. The cytotoxic activity of compounds 3-22 was carried out in vitro on L-1210 cells. The most active compounds were 9, 16, 18, and 20 in the seselin series and 10, 17, and 19 in the xanthyletin series. Structure-activity relationships are discussed.

Antiproliferative effects of compounds derived from plants of Northeast Brazil

“…Of the other phytochemicals studied, the pyranocoumarins xanthyletin and seselin have been evaluated regarding their cytotoxicity in vitro in L1210 murine leukaemia (Magiatis et al, 1998). However, this class of compounds may be more noted for their calcium channelblocking activity (Takeuchi, et al, 1991).…”

Ph3PAuNTf2 as a Superior Catalyst for the Selective Synthesis of 2H‐Chromenes: Application to the Concise Synthesis of Benzopyran Natural Products

“…Similarly, 16 [14] afforded only regioisomer 16a (precocene II) [16] in excellent yield. Moreover, the pyranocoumarins xanthyletin (17a) and seselin (17b), [17] compounds with surprisingly rich biological activities, [18] were synthesized in excellent yield from the smooth cyclization of 17. [14] Their relative product ratio was 17a/17b = 40:60.…”

Preparation, characterization and catalytic application of nano-Fe3O4@SiO2@(CH2)3OCO2Na as a novel basic magnetic nanocatalyst for the synthesis of new pyranocoumarin derivatives

“…Structural diversity associated with pyranocoumarins has resulted in a large number of new molecular entities, which have been found to be useful as anti-cancer, anti-oxidant, antiinammatory, anti-allergic, hepatoprotective, anti-viral, anticarcinogenic agents, enzyme inhibitor, and precursor of toxic substances. [13][14][15][16] In view of the biological, industrial, and synthetic importance of pyranocoumarins, several methods for their synthesis have been reported. [17][18][19] Although most of these processes have distinct advantages, the use of high temperatures, environmentally harmful catalysts, harsh reaction conditions, long reaction times and large quantity of volatile organic solvents limit the use of these methods.…”