Benzo phenanthridines

Reaction of Ar-Benzenesulfonyl-3-[bis(methyIthio)methyIenel-2r3-dihydro-l/F-quinoline-4-one 6.36 with Allyl and Benzyl Anions A New Regiospecific Synthesis of Phenanthridines and Benzo[/]phenanthridines... 

Loader and Timmons have described a number of photocyclizations which involve coupling with a heterocyclic ring in the presence of atmospheric oxygen. Irradiation of fraras-4-styrylquinoline (122) in hexane or cyclohexane gives 7,8-benzophenanthridine (124).161-163 In the latter solvent a small amount of 6-cyclohexyl-7,8-benzo-phenanthridine, resulting from the photochemical reaction between 7,8-benzophenanthridine and the solvent, has been isolated alkyla-... 

Although 6-methylphenanthridine cannot be oxidized satisfactorily with neutral or acid permanganate,246 Gopinath has shown that excess of selenium dioxide in boiling ethyl acetate converts the benzo-phenanthridine (240) (R = Me) into the corresponding acid (240)... 

Park and Cho [61] reported an extractive production system for benzo-phenanthridine alkaloids using cyclodextrins, in which production and some degree of separation occurred simultaneously. It was expected that the rapid removal of alkaloid produced from the suspension cultures was achieved by capturing alkaloid with cyclodextrins. In solid cultures of E. californica cells, alkaloid production was substantially enhanced (up to 40-fold) by the addition of /1-cyclodextrin. The enhancement of alkaloid production was also observed in suspension cultures, in which the major part of the alkaloids in the /J-cyclodex-trin treated cultures was present in the media, while the non-treated cultures contained the alkaloids in the cells. This indicated that /1-cyclodextrin not only captures the alkaloids but also helps in extracting them from cells. 

The purification of the commercially available sanguinarine (290) and a simplified isolation method were described (787a). Reports have appeared on thin-layer chromatographic methods of detection of benzo-phenanthridine alkaloids in Bocconia frutescens, Macleaya microcarpa, M. cordata (48), and Fumaria capreolata (788). A colorimetric method of determining the alkaloids in B. cordata has been reported (789). 

Stermitz et al. have recently reviewed the chemotaxonomy and the systematization of Papaver and Argemone plants (36, 833). They have also pointed out the characteristic features of the individual genera and sections from the viewpoint of the alkaloids. On the basis of the contained alkaloids, they have tried to differentiate the A. subfusiformis taxa from A. poly-anthemos (Scheme 20). According to these authors, the benzo-phenanthridine alkaloids (including the N-nor derivatives) may not be significant chemotaxonomic markers because they are formed in callus tissues (269). The alkaloids contained in the seeds of A. mexicana (grown in the U.S.S.R. and in Vietnam) have been studied (834). 

Cho, H.Y., Sung-Yong, H.Y., and Park, J.M. 2008. Differential induction of protein expression and benzo-phenanthridine alkaloid accumulation in Eschscholtzia califomica suspension cultures by methyl jas-monate and yeast extract. J. Microbiol. BiotechnoL, 18 255-262. 

In this small group of alkaloids, the 3-arylisoquinolines, as in the benzo-phenanthridines (see Sec. 21.1) to which they are clearly related, the nitrogen heterocycle can be either fully aromatic or saturated. All three members of the 3-arylisoquinolines have been isolated from Corydalis incisa, a plant also known to produce benzophenanthridines. 

Like tubocurarine, the quartemary benzo-phenanthridine sanguinarine is absorbed badly. It reacts with negatively charged and nucleophihc groups of proteins and inhibits several enzymes, e.g., Na /K -ATPase (Straub and Carver, 1975). In addition, it intercalates DNA due to its planar structure (Nandi and Maiti, 1985). 

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