477-49-6

Basic information

• Product Name: Podophyllotoxone
• Synonyms: Podophyllotoxone;(5aR)-5aα,6,8aβ,9-Tetrahydro-9α-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-5,8-dione;(5R)-5,5aα,8,8aβ-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6,9-dione;(5R)-5,8,8aβ,9-Tetrahydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6(5aαH),9-dione;(5R)-5aα,8aβ-Dihydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6,9(5H,8H)-dione;(5R)-5β-(3,4,5-Trimethoxyphenyl)-5,8,8aβ,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6,9(5aαH)-dione;Podophyllotoxinone;(-)-podophyllotoxon
• CAS NO: 477-49-6
• Molecular Formula: C₂₂H₂₀O₈
• Molecular Weight: 362.332
• Mol File: 477-49-6.mol

Chemical Properties

• Melting Point: 191.73℃
• Boiling Point: 602.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.365±0.06 g/cm3 (20 ºC 760 Torr)
• CAS DataBase Reference: Podophyllotoxone(CAS DataBase Reference)
• NIST Chemistry Reference: Podophyllotoxone(477-49-6)
• EPA Substance Registry System: Podophyllotoxone(477-49-6)

Safety Data

• Hazardous Substances Data: 477-49-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Podophyllotoxone is used as a chemotherapeutic agent for its significant cell apoptosis and antiproliferative effects against human PC-3 (prostate cancer) and Bcap-37 (breast cancer) cancer cell lines. It is particularly effective in targeting and treating these types of cancers, as it can inhibit the uncontrolled cell division and growth associated with cancerous cells.
Additionally, Podophyllotoxone has been found to have potential applications in other cancer types and is currently under investigation for its use in combination therapies to enhance the effectiveness of existing treatments and overcome drug resistance in cancer cells.

Upstream product

• 518-28-5 podofilox 
• 1180-34-3 podophyllotoxinyl acetate 
• 16481-54-2 podophyllotoxin-7′-O-β-D-glucopyranoside 
• 477-51-0 deoxypodophyllotoxin 
• 4375-07-9 epipodophyllotoxin 
• 64-19-7 acetic acid 
• 106636-74-2 4-bromo-4-deoxypodophyllotoxin 
• 106636-74-2 4β-bromo-4-desoxypodophyllotoxin 
• 24150-39-8 deoxypicropodophyllin 
• 40456-50-6 yatein 
• 161745-67-1 (4S)-4-isopropyl-3-[3-(3,4-methylenedioxyphenyl)propanoyl]-2-oxazolidinone 
• 477-48-5 podophyllotoxone 
• 67-56-1 methanol 
• 620116-42-9 (+)-isopicropodophyllone 

Downstream Products

• 42123-27-3 dehydropodophyllotoxin 
• 121976-16-7 (3aR)-2-phenyl-5c-(3,4,5-trimethoxy-phenyl)-(3ar)-3,3a,4,5-tetrahydro-2H-[1,3]dioxolo[4',5':4,5]benzo[1,2-g]indazole-4c-carboxylic acid 
• 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 
• 78391-86-3 neoanhydropicropodophyllol 
• 154462-13-2 epipicropodophyllol 
• 4375-06-8 epipicropodophyllotoxin 
• 477-47-4 picropodophyllotoxin 
• 3811-15-2 picropodophyllol 
• 120090-82-6 thuriferic acid 
• 177990-69-1 isoxazolopodophyllic acid 

Relevant articles and documents

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.

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.

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.

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.

HAPTENS, HAPTEN CONJUGATES, COMPOSITIONS THEREOF AND METHOD FOR THEIR PREPARATION AND USE

A method for performing a multiplexed diagnostic assay, such as for two or more different targets in a sample, is described. One embodiment comprised contacting the sample with two or more specific binding moieties that bind specifically to two or more di

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.

Synthesis and insecticidal activity of novel hydrazone compounds derived from a naturally occurring lignan podophyllotoxin against Mythimna separata (Walker)

In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, a series of novel hydrazone derivatives of podophyllotoxin, which is a naturally occurring aryltetralin lignan and isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum species, were synthesized and evaluated as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. Especially compounds 8i, 8j, 8t, and 8u showed the more potent insecticidal activity with the final mortality rates greater than 60%.