Aryltetralin lignans: chemistry, pharmacology and biotransformations.

  title={Aryltetralin lignans: chemistry, pharmacology and biotransformations.},
  author={Bruno Botta and Giuliano Delle Monache and D. Misiti and Alberto Vitali and Giovanni Zappia},
  journal={Current medicinal chemistry},
  volume={8 11},
Podophyllotoxin derivatives like etoposide 7a, etophos 7b, and teniposide 7c are used clinically as potent chemotherapeutic agents for a variety of tumors including small cell lung carcinoma, testicular cancer, and malignant lymphoma. These compounds derived from a series of modifications which converted podophyllotoxin 1a from an entity that interacted with tubulin and blocks mitosis to one that induced a block in late S or early G2 by interacting with topoisomerase II. Synthetic studies on… 
Lignans and neolignans as lead compounds
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Podophyllotoxin: Current Perspectives
This review provides a detailed discussion of research advances in the synthetic and medicinal chemistry of podophyllotoxin, and addresses the short history and pharmacological action of these compounds and further outlines the preclinical development and clinical trials of drugs in the pipeline and marketing approval.
Podophyllotoxin: Current approaches to its biotechnological production and future challenges
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Design, synthesis, and biological evaluation of novel pyridine acid esters of podophyllotoxin and esters of 4′-demethylepipodophyllotoxin
It is suggested that the cytotoxic activity of OCH3 at C-4′ is more potent than that of its demethylated analogs and the podophyllotoxin substitution atC-4 may be optimal for synthesizing more potent cytot toxic compounds.
Recent Progress on C‐4‐Modified Podophyllotoxin Analogs as Potent Antitumor Agents
This review focuses on a second generation of new etoposide‐related drugs and provides detailed coverage of the current status and recent development of C‐4‐modified PPT analogs as anticancer clinical trial candidates.
The Catalytically Lignan-Activation-Based Approach for the Synthesis of (epi)-Podophyllotoxin Derivatives.
The first catalytic and lignan-activation-based approach for (epi)-podophyllotoxin derivatization was established, featuring an in situ anomerization of the hemiacetal OHs in the critical condensation step.
Asymmetric Chemoenzymatic Synthesis of (-)-Podophyllotoxin and Related Aryltetralin Lignans.
A short chemoenzymatic total synthesis of (-)-podophyllotoxin and related aryltetralin lignans is reported, using an enzymatic oxidative C-C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion.
Advances in the Synthesis of Aryltetralin Lignan Lactones
Etoposide and tenoposide, derivatives of the aryltetralin lignan lactone podophyllotoxin (5), are clinically important anticancer agents. The structure of podophyllotoxin includes four contiguous
Small Cells for Big Ideas: The Cytotoxic Podophyllotoxin and the Long Journey in Discovering Its Biosynthetic Pathway
Compelling discoveries and unexpected turns of the lignan biosynthetic pathway are discussed next, followed by benchmark studies in the aseptic cultivation of the plants producing it.
Updated biotechnological approaches developed for 2,7′‐cyclolignan production 1
Exploration and development of biosynthetical pathways leading to 2,7′‐cyclolignans may open paths for future metabolic engineering, such as the bioconversion of deoxypodophyllotoxin to epipodophyLLotoxin employing a human hepatic enzyme heterologously expressed in Escherichia coli.