Anthranilic acid derived alkaloids

Anthranilic acid Anthranilic acid-derived alkaloids Tme alkaloids Quinazoline alkaloids Quinoline alkaloids Acridine alkaloids... 

Groeger D (1984) Biosynthesis of Anthranilic Acid Derived Alkaloids. In van der Plas HC, OtvOs L, Simonyi M (eds) Bio-Organic Heterocycles. Synthetic, Physical and Pharmacological Aspects. Elsevier, Amsterdam, p 165... 

Anthranilic Anthranilic acid-derived True alkaloids... 

Of all the alkaloid-producing families, one of the most prolific is the Rutaceae (Waterman, 1975). The alkaloids obtained included 1-benzyltetrahydroisoquinoline, simple tryptophan derivatives, imidazoles and, most commonly, quinoline alkaloids originating from anthranilic acid. The Rutaceae was the only family in which the direct use of anthranilic acid in alkaloid production occurs to any extent. 

A new and very neat synthesis of evodiamine and rutaecarpine is described by the authors as a retro mass spectral synthesis , since the original conception was derived from the mode of fragmentation of these alkaloids in the mass spectrometer this involves a familiar retro Diels-Alder fission of ring c. Evodiamine (16a) was thus constructed by a 27r + 47r cycloaddition of 3,4-dihydro-/8-carboline with the keteneimine (17), prepared in situ by elimination of sulphur dioxide from the sulphinamide anhydride (18) (Scheme 7). When the anthranilic acid derivative (19) was used the product was rutaecarpine (20) itself, the initially formed dihydro-... 

Various unclassified alkaloids (aniline and anthranilic acid derivatives, cinnamic acid amides, guanidine bases, and oxazoles) are briefly reviewed in a general text on alkaloids.30... 

The same general intermediate (342 X = OOH) may be invoked in the reaction of tetrahydro-jS-carboUne derivatives with perbenzoic acid and ozone. From the reaction [342 (X = OOH) 353-> 353a] a cyclic lactam (353a) may be isolated. Such a structure is presumably the intermediate in the oxidative degradation of numerous complex tetrahydro-)S-carboline alkaloids, which yields A-oxalyl-anthranilic acid derivatives (354). The lactam can undergo base-... 

The route of formation of the carbazole nucleus is still far from understood, and has been variously considered to arise from 3-prenylquinolone via a pathway involving shikimic acid (394) and mevalonic acid (MVA) (400) (Scheme 3.1) (1,112,362-366), anthranilic acid (397) and prephenic acid (404) via a pathway involving shikimic acid (394) (Scheme 3.2) (367), and also tryptophan (408) involving the mevalonate (400) pathway (Scheme 3.3) (133). All of these pathways lack experimental proof. However, based on the occurrence of the diverse carbazole alkaloids derived from anthranilic acid (397) in the family Rutaceae, the pathway... 

Alkaloids derived from L-tryptophan hold the indole nucleus in a ring system. The ring system originates in the shikimate secondary compounds building block and the anthranilic acid pathway. It is known that the shikimate block. 

Anthranilic acid (2-aminobenzoic acid) (see page 126) is another shikimate-derived compound which, as its CoA ester anthraniloyl-CoA, can act as a starter unit for malonate chain extension. Aromatization of the acetate-derived portion then leads to quinoline or acridine alkaloids, according to the number of acetate units incorporated (Figure 3.47). These products are similarly discussed elsewhere, under alkaloids (Chapter 6, page 376). 

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