Synthesis and biological evaluation of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents

Wang, Li; Yang, Fenyan; Yang, Xiaochun; Guan, Xianghong; Hu, Chunqi; Liu, Tao; He, Qiaojun; Yang, Bo; Hu, Yongzhou

doi:10.1016/j.ejmech.2010.11.016

Cited by 24 publications

(9 citation statements)

References 13 publications

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“…Schiff bases are efficient antimicrobial agents (4) due to their ability to adsorb onto the cellular membrane. Enhancing the antimicrobial activity of the Schiff bases includes the introduction of some function groups to their chemical structures, e.g., SH, NH, OH (5) , heterocyclic or halogens (6)(7) . Another important feature of A the antimicrobial agents nowadays, is their ability for biodegradation (8) which makes them environmentally safe.…”

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confidence: 99%

Synthesis and Inhibitory Activity of Schiff base Surfactants Derived from Tannic Acid Against Bacteria and Fungi

2012

Egypt. J. Chem.

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SERIES of tannic acid Schiff base surfactants were synthesized and their structures were elucidated using microelemental analysis, FTIR and 1 H-NMR data. The molecular weights were determined using viscosity measurements and gel permeation chromatography. The surface activities of the surfactants were determined by surface tension measurements. The antimicrobial activity and minimum inhibitory concentrations were evaluated by disk diffusion assay against gram-positive, gram-negative bacteria and fungi. The antimicrobial data disclosed that the tested compounds demonstrated moderate to excellent microbial inhibitions. Compounds TGB 1 showed high potency against the tested strains.

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confidence: 99%

Synthesis and Inhibitory Activity of Schiff base Surfactants Derived from Tannic Acid Against Bacteria and Fungi

2012

Egypt. J. Chem.

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“…On the other hand, O -demethylation at the C-4′ and epimerization of the C-7 position of podophyllotoxin, 1 , followed by replacement by an aromatic diamine-type linker, gave rise to the other fragment of the hybrid, 3 , in a one-pot reaction [ 35 ]. Finally, aldehyde 2 was condensed with the 7β-cyclolignan 3 through an imine-type bond, obtaining the final 7β,9-biscyclolignan 4 ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Podophyllic aldehyde ( 2 ) was synthesized from podophyllotoxin as described in our previous works [ 35 ].…”

Section: Methodsmentioning

confidence: 99%

A Novel Cytotoxic Conjugate Derived from the Natural Product Podophyllotoxin as a Direct-Target Protein Dual Inhibitor

et al. 2020

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Natural products are the ideal basis for the design of novel efficient molecular entities. Podophyllotoxin, a naturally occurring cyclolignan, is an example of natural product which displays a high versatility from a biological activity point of view. Based on its unique chemical structure, different derivatives have been synthesized presenting the original antitumoral properties associated with the compound, i.e., the tubulin polymerization inhibition and arising anti-topoisomerase II activity from structural modifications on the cyclolignan skeleton. In this report, we present a novel conjugate or hybrid which chemically combines both biological activities in one single molecule. Chemical design has been planned based in our lead compound, podophyllic aldehyde, as an inhibitor of tubulin polymerization, and in etoposide, an approved antitumoral drug targeting topoisomerase II. The cytotoxicity and selectivity of the novel synthetized hybrid has been evaluated in several cell lines of different solid tumors. In addition, these dual functional effects of the novel compound have been also evaluated by molecular docking approaches.

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“…As outlined in Table , Wang et al . synthesized three series of new 4β‐anilino‐DEPPT derivatives ( 585–613 ) for cytotoxicity evaluation against four human cancer cell lines, KB, KB/VCR, A549, and 95D.…”

Section: Hemisynthesis and Structure–activity Relationshipsmentioning

confidence: 99%

Recent Progress on C‐4‐Modified Podophyllotoxin Analogs as Potent Antitumor Agents

Liu

Tian

Qian

et al. 2014

Medicinal Research Reviews

103

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Podophyllotoxin (PPT), as well as its congeners and derivatives, exhibits pronounced biological activities, especially antineoplastic effects. Its strong inhibitory effect on tumor cell growth led to the development of three of the most highly prescribed anticancer drugs in the world, etoposide, teniposide, and the water-soluble prodrug etoposide phosphate. Their clinical success as well as intriguing mechanism of action stimulated great interest in further modification of PPT for better antitumor activity. The C-4 position has been a major target for structural derivatization aimed at either producing more potent compounds or overcoming drug resistance. Accordingly, numerous PPT derivatives have been prepared via hemisynthesis and important structure–activity relationship (SAR) correlations have been identified. Several resulting compounds, including GL-331, TOP-53, and NK611, reached clinical trials. Some excellent reviews on the distribution, sources, applications, synthesis, and SAR of PPT have been published. 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.

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Synthesis and biological evaluation of new 4β-anilino-4′-O-demethyl-4-desoxypodophyllotoxin derivatives as potential antitumor agents

Cited by 24 publications

References 13 publications

Synthesis and Inhibitory Activity of Schiff base Surfactants Derived from Tannic Acid Against Bacteria and Fungi

Synthesis and Inhibitory Activity of Schiff base Surfactants Derived from Tannic Acid Against Bacteria and Fungi

A Novel Cytotoxic Conjugate Derived from the Natural Product Podophyllotoxin as a Direct-Target Protein Dual Inhibitor

Recent Progress on C‐4‐Modified Podophyllotoxin Analogs as Potent Antitumor Agents

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