Synthesis and cytotoxicity of 17E-(2-aryl-2-oxo-1-ethylidene)-5α-androstane derivatives

Li, Yan; Huang, Jie; Liu, Jinliang; Yan, Peiyun; Liu, Hui; Sun, Qian; Wang, Xingbin; Wang, Cunde

doi:10.1016/j.steroids.2011.10.003

Cited by 13 publications

(5 citation statements)

References 22 publications

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“…One application has been reported also in the field of steroids (Scheme 48). [101] The authors designed some androstane derivatives 197 for screenings in cancer area. The classical olefination procedures starting from epiandrosterone 194 did not allow the synthesis of the desired enones 196 and therefore an MSR was considered.…”

Section: Use Of Meyer Schuster Rearrangement In the Total Synthesis Omentioning

confidence: 99%

Recent Developments in the Meyer‐Schuster Rearrangement

Justaud¹,

Hachem

Grée³

2021

Eur J Org Chem

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Most of this review article has been prepared during Covid 19 pandemy. Therefore, we dedicate it,-first to all persons who unfortunately died from this disease and,-second to all people (medical doctors and many others) who helped their congeners to survive to this pandemy. The Meyer-Schuster rearrangement is an efficient method to prepare α,β-unsatured carbonyl compounds starting from propargylic alcohols and this review presents the remarkable progress made during the last decade in this reaction. New efficient catalytic systems have been discovered and many elegant applications have been reported for this rearrangement. To be noticed in particular are the new and efficient cascade processes affording a wide range of carbo-and heterocyclic molecules. Moreover, brilliant applications of this rearrangement have been described as well, in the total synthesis of complex natural products and their analogues. Finally, the first examples of aza-Meyer-Schuster rearrangements have been recently described as well.

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Section: Use Of Meyer Schuster Rearrangement In the Total Synthesis Omentioning

confidence: 99%

Recent Developments in the Meyer‐Schuster Rearrangement

Justaud¹,

Hachem

Grée³

2021

Eur J Org Chem

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“…The results from [ 35 , 36 ] add considerable support for the statement that 5 α -androstan-16-one and similar compounds from aquatic macrophytes can serve as perspective anticancer agents which can inhibit proliferation of cancer cell lines. There are also the immediate and long-term prospects for use of these constitutes as agents against the resistant fungal strains, combined with systemic fungal infections [ 37 ].…”

Section: Resultsmentioning

confidence: 77%

Assessment of the Potential Biological Activity of Low Molecular Weight Metabolites of Freshwater Macrophytes with QSAR

et al. 2016

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The paper focuses on the assessment of the spectrum of biological activities (antineoplastic, anti-inflammatory, antifungal, and antibacterial) with PASS (Prediction of Activity Spectra for Substances) for the major components of three macrophytes widespread in the Holarctic species of freshwater, emergent macrophyte with floating leaves, Nuphar lutea (L.) Sm., and two species of submergent macrophyte groups, Ceratophyllum demersum L. and Potamogeton obtusifolius (Mert. et Koch), for the discovery of their ecological and pharmacological potential. The predicted probability of anti-inflammatory or antineoplastic activities above 0.8 was observed for twenty compounds. The same compounds were also characterized by high probability of antifungal and antibacterial activity. Six metabolites, namely, hexanal, pentadecanal, tetradecanoic acid, dibutyl phthalate, hexadecanoic acid, and manool, were a part of the major components of all three studied plants, indicating their high ecological significance and a certain universalism in their use by various species of water plants for the implementation of ecological and biochemical functions. This report underlines the role of identified compounds not only as important components in regulation of biochemical and metabolic pathways and processes in aquatic ecological systems, but also as potential pharmacological agents in the fight against different diseases.

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“…It was found that introducing heterocycles into steroids, [7][8][9][10][11][12] by modification of the steroidal side chain or substitution of the steroidal skeleton, can result in a change in its biological activities. [13][14][15][16][17] Steroids containing heteroatoms have been widely researched and reported.…”

Section: Introductionmentioning

confidence: 99%