N , C -Coupled naphthylisoquinoline alkaloids: a versatile new class of axially chiral natural products

Covering: up to April 2021During the past decades, a plethora of natural products with restricted rotation about a biaryl axis have been discovered, among them the naphthylisoquinoline (NIQ) alkaloids, mostly , -coupled and having remarkable bioactivities. Within this fascinating class of naturally...

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Bibliographic Details
Published in:Natural product reports 2021-12, Vol.38 (12), p.2154-2186
Main Authors: Tajuddeen, Nasir, Bringmann, Gerhard
Format: Article
Language:English
Subjects:
Alkaloids
Alkaloids - chemical synthesis
Alkaloids - isolation & purification
Alkaloids - pharmacology
Anticancer properties
Antineoplastic Agents, Phytogenic - chemical synthesis
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Antiparasitic agents
Biological Products - chemical synthesis
Biological Products - isolation & purification
Biological Products - pharmacology
Caryophyllales - chemistry
Chirality
Humans
Isoquinolines - chemical synthesis
Isoquinolines - isolation & purification
Isoquinolines - pharmacology
Leukemia
Leukemia - drug therapy
Molecular Structure
Natural products
Stereoisomerism
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Summary:Covering: up to April 2021During the past decades, a plethora of natural products with restricted rotation about a biaryl axis have been discovered, among them the naphthylisoquinoline (NIQ) alkaloids, mostly , -coupled and having remarkable bioactivities. Within this fascinating class of naturally occurring biaryl compounds, NIQ alkaloids bearing an , -heterobiaryl axis have attracted particular attention. They are structurally and biosynthetically unprecedented, with interesting stereochemical implications and biological activities. In contrast to existing articles and reviews about axially chiral - yet , -coupled - natural products, this is the first, comprehensive review on the new subclass of , -coupled NIQs, their isolation and structural elucidation, their , -axial chirality, their biosynthetic origin, their promising antiparasitic and antileukemic activities, and their total synthesis.
ISSN:0265-0568
1460-4752
DOI:10.1039/d1np00020a