1 -Hydroxy-3-methoxy-10-methylacridone

Trihydroxy-4-methoxy-10-methyl-2,8-bw(3-methylbut-2-enyl) acridin-9( 10/7)-one, 1,5 -dihydroxy-2,3 -dimethoxy-10-methyl-9-acridone, 2,3-dihydro-4,9-dihydroxy-2-(2-hydroxy-propan-2-yl)-l 1-methoxy-10-methylfuro[3,2-b]acridin-5(1077)-one, 3,4-Dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2/7-pyrano[2,3-a]acridin-12(7/7)-one, 3,4-Dihydro-3,5,8-trihydroxy-6-methoxy-2,2,7-trimethyl-2/7-pyrano[2,3-a]acridin-12(7/7)-one, l-hydroxy-3-methoxy-10-methyl-9-acridone, 1 -hydroxy-2,3 -dimethoxy-10-methyl-9-acridone, 1 -hydroxy-A-methylacridone, l-methyl-2-[(Z)-pentadec-9-enyl]quinolin-4(l/7)-one,... 

Anti-HIV activity 1 -Hydroxy-W-methylacridone, 2-(pent-1 -enyl)quinoline, 2-(pent-2-en) quinolin, 2-acetyl-4(3H)-quinazolinone, 2- -pentylquinoline, 3-prenyl-4-prenyloxyquinolin-2-one, 4-methoxy-l-methylquinolin-2-one, )V-methyl-3,3-diprenylquinoline-2,4-dione, buchapine, y-fagarine, haplopine, (-1-)-platydesmine, uranidine [28, 30, 34, 38,40,41],... 

A further study of the root alkaloids of Ruta graveolens has resulted in the identification of a new chlorine-containing acridone (31), named iso-gravacridonchlorine.29 The same source yielded an inseparable mixture of alkaloids, shown by n.m.r. spectroscopy to consist of the new compound furacridone (32) and the known compound l-hydroxy-3-methoxy-N-methylacridone (29 R = H) in a ratio of 4 1. 

Pharmazie, 1975, 30, 753). Two new acridones, l-hydroxy-3,4-dimethoxy-lO-methylacridone (25) and l-hydroxy-3-geranyloxy-4-methoxy-lO-methylacridone (26) occur in extracts of the plant Sarcomelicope leiocarpa indigenous to New Caledonia together with eight other known structures (G. Baudouin et al., J.nat. Prod., 1985, 48, 260). 

Five acridone alkaloids were obtained previously from the bark of Teclea boiviniana cf. Vol. 6, p. 108) a recent investigation showed that the constituents of the leaves are similar, and resulted in the isolation of arborinine (37 R = H), tecleanthine (38 R = H, R = OMe), evoxanthine (38 R = R = H), 6-methoxytecleanthine (38 R = R = OMe), and 1,3,4-trimethoxy-iV-methyl-acridone (39 R = Me, R = OMe). The latter compound has not been obtained previously from a natural source. The n.m.r. and mass spectra indicated that the new alkaloid was a trimethoxy-iV-methylacridone and that ring A was unsubstituted. The three possible acridones had been synthesized earlier, and from melting-point data the alkaloid appeared to be the 1,3,4-trimethoxy-derivative this was confirmed by synthesis using a modification of the published procedures. 1,2,3-Trimethoxy-iV-methylacridone (37 R = Me), previously isolated from Evodia alata, has now been obtained from Melicope leratii. The known alkaloids melicopidine (40 R = Me, R = OMe) and xanthovedine (40 R = R = H) were also shown to be constituents of M. leratii. Arborinine (37 R = H) has been obtained from Vepris pilosa and from Ruta chalapensis. Other known acridone alkaloids isolated from a new source include the l-hydroxy-3-methoxy-deriva-tive (39 R = R = H) and its methyl ether (39 R = Me, R = H), from Vepris pilosa. ... 

Alkaloids considered in this section derive biogenetically from 1,3-dihydroxy-lO-methylacridone (19) and 1,3-dihydroxyacridone (22) by simple deoxygenation and/or oxidation of the acridone aromatic skeleton. Subsequent O-alkylation very often takes place, and most natural acridones bear methoxy or methylenedioxy substituents. A few, exemplified by vebilocine (27) (94), evoprenine (28) (95), and 3-graanyloxy-l-hydroxy-4-methoxy-10-methylacridone (29) (96), are also substituted by prenyloxy or geranyloxy groups. 

This versatile methodology was successfiiUy q[>plied, with slight modifications, for the synthesis of a number of other aciidone alkaloids, including l-hydroxy-3-methoxy-lO-methylacridone (48) 301), 1,3-dimethoxy-lO-methylacridone (53) 301, 302), 1,3-dihydroxy-lO-methylacridone (19) 301, 302), 1,2,3-trimethoxy-lO-methylacridone (73) 303), xanthoxoline (58) 30S), and l,5-dihydn)xy-2,3-dimethoxy-lO-methylacridone (S-hydroxyaiborinine) (75) 188). 

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