130322-38-2

Upstream product

• 477-51-0 deoxypodophyllotoxin 
• 4375-07-9 epipodophyllotoxin 
• 518-28-5 podofilox 
• 64-19-7 acetic acid 
• 106636-74-2 4β-bromo-4-desoxypodophyllotoxin 
• 40456-50-6 yatein 
• 161745-67-1 (4S)-4-isopropyl-3-[3-(3,4-methylenedioxyphenyl)propanoyl]-2-oxazolidinone 
• 131897-56-8 2,2-Dimethyl-propionic acid (5S,5aR,6R,8aR,9S)-9-hydroxy-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester 
• 56579-86-3 2-(3,4-methylenedioxyphenyl)-1,3-dithiane 
• 67-56-1 methanol 
• 620116-42-9 (+)-isopicropodophyllone 
• 24150-39-8 deoxypicropodophyllin 
• 16481-54-2 podophyllotoxin-7′-O-β-D-glucopyranoside 
• 1180-34-3 podophyllotoxinyl acetate 

Downstream Products

• 55515-07-6 (1α,2α,3α)-podophyllotoxin 
• 157904-78-4 <5R-(5α,6α)>-5,6,7,8-tetrahydro-7-methylidene-8-oxo-5-(3,4,5-trimethoxyphenyl)naphtho<2,3-d><1,3>dioxole-6-carboxylic acid 
• 477-48-5 (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione 
• 4375-07-9 epipodophyllotoxin 
• 518-28-5 podofilox 
• 120090-82-6 thuriferic acid 
• 191283-12-2 (Z)-podophyllotoxone O-methyloxime 
• 93780-84-8 4'-demethylpodophyllotoxone 
• 477-47-4 picropodophyllotoxin 
• 172096-08-1 [(3aR,4R,5R)-2-Phenyl-5-(3,4,5-trimethoxy-phenyl)-3,3a,4,5-tetrahydro-2H-7,9-dioxa-1,2-diaza-dicyclopenta[a,g]naphthalen-4-yl]-methanol 
• 211043-39-9 (5R,6R,7R)-methyl 7-(hydroxymethyl)-8-oxo-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylate 
• 211043-47-9 (5R,6R,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid propyl ester 
• 124131-03-9 (5R,6R,7R)-7-Hydroxymethyl-8-oxo-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis and biological evaluation of podophyllotoxin congeners as tubulin polymerization inhibitors

A series of new podophyllotoxin derivatives containing structural modifications at C-7, C-8, and C-9 were synthesized and evaluated for their cytotoxic activity against three human cancer cell lines. All the synthesized compounds showed significant growth inhibition with GI50values in micromolar levels while some of the compounds were several times more potent against MCF-7 and HeLa cell lines than MIAPACA cell line. Three compounds (12a, 12d and 12e) emerged as potent compounds with broad spectrum of cytotoxic activity against all the tested cell lines with GI50values in the range of 0.01-2.1 μM. These compounds induce microtubule depolymerization and arrests cells at the G2/M phase of the cell cycle. Moreover, compounds 12d and 12e disrupted microtubule network and accumulated tubulin in the soluble fraction in a similar manner to their parent podophyllotoxin scaffold. In addition, structure activity relationship studies within the series were also discussed. Molecular docking studies of these compounds into the colchicine-binding site of tubulin, revealed possible mode of inhibition by these compounds.

CYTOTOXIC LIGNANS FROM PODOPHYLLUM, AND THE NOMENCLATURE OF ARYLTETRALIN LIGNANS

Roots of Podophyllum hexandrum and P. peltatum both contain (1R,2R,3R)-desoxypodophyllotoxin and the previously unreported (1R,2R,3R)-podophyllotoxone .Thermal isomerization of (1α,2α,3β)-pod

A novel enzymatic dehydrogenation of podophyllotoxin congeners by yeast cells

The biotransformation of aryltetralin lignans to arylnaphthalene lignans in presence of yeast is described. Podophyllotoxone, an oxidation product of podophyllotoxin on incubation with yeast from different sources produced dehydropodophyllotoxin, an important representative of arylnaphthalene lignans.

A new approach to the synthesis of podophyllotoxin based on epimerization reactions

A formal synthesis of podophyllotoxin has been achieved by means of the well known conjugate addition-alkylation of 5H-furan-2-one, followed by cyclization and controlled epimerizations. This approach represents a useful new route to the 8,7'-trans-stereo

Synthesis and In Vitro Anticancer Activity of Triazolyl Analogs of Podophyllotoxin, a Naturally Occurring Lignin

Abstract: A series of triazolyl-modified podophyllotoxin analogs have been designed and synthesized by utilizing Huisgen 1,3-dipolar cycloaddition in order to develop potent antitumor agents. The synthesized analogs were assessed for in vitro anticancer a

Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3

A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of p-methoxybenzyl ethers.

Base-free oxidation of alcohols enabled by nickel(ii)-catalyzed transfer dehydrogenation

An efficient nickel(ii)-catalyzed transfer dehydrogenation oxidation of alcohols is reported that relies on cyclohexanone as the formal oxidant and does not require the use of an external base. The synthetic utility of this protocol is demonstratedviathe facile oxidation of structurally complicated natural products.

Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans

(?)-Podophyllotoxin is one of the most potent microtubule depolymerizing agents and has served as an important lead compound in antineoplastic drug discovery. Reported here is a short chemoenzymatic total synthesis of (?)-podophyllotoxin and related aryltetralin lignans. Vital to this approach is the use of an enzymatic oxidative C?C coupling reaction to construct the tetracyclic core of the natural product in a diastereoselective fashion. This strategy allows gram-scale access to (?)-deoxypodophyllotoxin and is readily adaptable to the preparation of related aryltetralin lignans.

Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones

Podophyllotoxin is probably the most prominent representative of lignan natural products. Deoxy-, epi-, and podophyllotoxin, which are all precursors to frequently used chemotherapeutic agents, were prepared by a stereodivergent biotransformation and a biocatalytic kinetic resolution of the corresponding dibenzylbutyrolactones with the same 2-oxoglutarate-dependent dioxygenase. The reaction can be conducted on 2 g scale, and the enzyme allows tailoring of the initial, “natural” structure and thus transforms various non-natural derivatives. Depending on the substitution pattern, the enzyme performs an oxidative C?C bond formation by C?H activation or hydroxylation at the benzylic position prone to ring closure.

Divergent Asymmetric Syntheses of Podophyllotoxin and Related Family Members via Stereoselective Reductive Ni-Catalysis

A nickel-catalyzed reductive cascade approach to the efficient construction of diastereodivergent cores embedded in podophyllum lignans is developed for the first time. Their gram-scale access paved the way for unified syntheses of naturally occurring podophyllotoxin and other members.