Protoberberine

The nomenclature and numbering of formulas for berberine and its derivatives is based on the system adopted by Buck, Perkin and Stevens for the parent substance of the series, protoberberine (XXIV). Awe has suggested that tetrahydroproioberberine should be called berbine and used as the basis of a system of names for these alkaloids. [Pg.336]

A related route to the protoberberine skeleton was reported by Lete, in which substrate 54 underwent Bischler-Napieralski reaction followed by intramolecular alkylation of an in situ generated alkyl chloride to afford 55. °... [Pg.383]

This problem has been circumvented by utilizing the ipso-directing capability of a silicon substituent at the 2 position of the D ring to facilitate ring closure at this position. Benzylisoquinoline 26 condensed with formaldehyde to give predominantly product 28 when R = H. However, when R = SiMea, 27 was the only product observed and was isolated in excellent yield.Several members of the protoberberine family of natural products have been synthesized using this strategy. [Pg.472]

Interaction of Protoberberine Alkaloids with Nucleic Acid Structures. . . 176... [Pg.155]

Protoberberine Alkaloid-Triplex Nucleic Acid Interaction. 194... [Pg.156]

Protoberberine Alkaloid-Nucleic Acid Quadruplex Interaction. 196... [Pg.156]

Abstract Protoberberine alkaloids and related compounds represent an important class of molecules and have attracted recent attention for their various pharmacological activities. This chapter deals with the physicochemical properties of several isoquinoline alkaloids (berberine, palmatine and coralyne) and many of their derivatives under various environmental conditions. The interaction of these compounds with polymorphic DNA structures (B-form, Z-form, H -form, protonated form, triple helical form and quadruplex form) and polymorphic RNA structures (A-form, protonated form, triple helical form and quadruplex form) reported by several research groups, employing various analytical techniques such as spectrophotometry, spectrofluorimetry, circular dichro-ism, NMR spectroscopy, viscometry as well as molecular modelling and thermodynamic analysis to elucidate their mode and mechanism of action for structure-activity relationships, are also presented. [Pg.156]

Protoberberine Alkaloids Physicochemical and Nucleic Acid Binding Properties 157... [Pg.157]

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