Chemistry of Acronycine; Part 1. Synthesis of 1-Hydroxy-1,2-dihydroacronycine and 2-Hydroxy-1,2-dihydroacronycine

Abstract

The synthesis of the potential acronycine prodrugs, 1-hydroxy-1,2-dihydroacronycine ( 2) and 2-hydroxy-1,2-dihydroacronycine ( 3) are described using the natural alkaloid acronycine ( 1) as starting material.

2,2-dimethyl-2H-pyran-derived alkaloids I. Practical synthesis of acronycine and benzo[b]acronycine and their biological properties

“…Most of the attempts to improve the activity of acronycine by structural modifications have been focused on the modification on pyran moiety specially on 1,2-double bond by hydration (Mitaku et al, 1988), epoxidation (Reisch and Top, 1991;Reisch and Schiwek, 1994) or dihydroxylation (Elomri et al, 1996;Costes et al, 1999;Magiatis et al, 1999), substitution of 6-OCH 3 group by O-alkyl, O-alkenyl, and others (Schneider et al, 1972), and annulation of benzene ring on to ring-A (Costes et al, 2000;Nguyen et al, 2006). On the other hand, modifications of acronycine by introducing (a) substituent(s) on to ring-A are limited (Svododa, 1966;Svododa et al, 1966;Smolders et al, 1982;Smolders et al, 1984;Blechert et al, 1980;Reisch et al, 1993) only with very limited substituents.…”

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

“…(±)- trans -4‘-Hydroxy-3‘-bromo-3‘,4‘-dihydroseselin ( 7 ) and (±)- trans -4‘-hydroxy-3‘-bromo-3‘,4‘-dihydroxanthyletin ( 8 ) were obtained by treatment of 1 and 2 , respectively, with NBS in aqueous THF solution . The bromohydrins 7 and 8 were smoothly debrominated with tributyltin hydride, to 9 and 10 , respectively.…”

“…The 1 H NMR spectrum of 9 showed characteristic signals at δ = 5.02 (1H, ddd, J = 4.8, 4.4, 3.0 Hz, dd, J = 4.8, 3.0 Hz after addition of D 2 O), 5.30 (1H, d, J = 4 Hz, exch with D 2 O), 2.05 (1H, dd, J = 14.6, 3.0 Hz) and δ = 1.93 (1H, dd, J = 14.6, 4.8 Hz), which are in agreement with those described for other natural and hemisynthetic products containing the dimethylpyrano ring system , of 12 and 13 . The 13 C NMR spectrum of 9 also showed a signal pattern of the dimethylpyrano ring similar to that of 12 .…”

Design and synthesis of some new pyranoxanthenones with cytotoxic activity

“…However, in clinical trials success was limited, partially due to its extremely low water solubility [3]. In a search for compounds with better selectivity and higher potency, several structural modifications of acronycine have been reported, involving substitutions on the acridone chromophore, like 11-methoxyacronycine and the pyran moiety of the molecule as well [4][5][6].…”