Synthesis of methoxycarbonylpyrazolylandrostene derivatives, and their potential inhibitory effect on androgen biosynthesis and cell proliferation

Szabó, Nikoletta; Iványi, Zoltán; Szécsi, Mihály; Julesz, J.; Mernyák, Erzsébet; Huber, Judit; Wölfling, János; Minorics, Renáta; Zupkó, István; Schneider, Gyula

doi:10.1016/j.steroids.2015.03.008

Cited by 17 publications

(3 citation statements)

References 34 publications

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“…In order to get more steroidal N‐heterocyclic derivatives, it is key step to synthesize a reactive intermediate with β ‐hydroxy‐ α , β ‐unsaturated ketone in steroidal skeleton, which was widely used in the construction of different N‐heterocyclic systems [21–23] . Hence, when β ‐hydroxy‐ α , β ‐unsaturated ketone intermediate ( 1a ) was successfully obtained in hand, a series of novel pregnenolone derivatives ( 1b – 1g ) were synthesized by following the synthetic route outlined in Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Anticancer Activity of Novel Steroidal Derivatives with D‐Ring Fused or Substituted N‐Heterocyclic Systems

Yang

Luo

et al. 2022

Chemistry & Biodiversity

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A series of novel D-ring fused or substituted steroidal N-heterocycles were synthesized, and their chemical structures were characterized by spectroscopic analysis. The anticancer activity of these compounds against four human cancer cell lines (MCF-7, H1299, HeLa and HepG2) were evaluated and the structure-activity relationship (SAR) was also investigated. Compound 3c displayed significant inhibitory activity on the four cancer cells with IC 50 values ranging from 3.88 to 10.05 μM. Overall, these studies indicated that construction of N-heterocyclic system with D-ring substituted containing a double bond at C-16 and C-17 or D-ring fused with [17,16-d] azolo [1,5-a]pyrimidine could be a promising strategy to improve antitumor activity for steroids deserved further investigation.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Anticancer Activity of Novel Steroidal Derivatives with D‐Ring Fused or Substituted N‐Heterocyclic Systems

Yang

Luo

et al. 2022

Chemistry & Biodiversity

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“…В работе [52] были синтезированы стероидные пиразолы, содержащие ароматический заместитель при N1 или N2 и метоксикарбонильный заместитель при С¢5 в гетероцикле (186-215). Синтезированные соединения были тестированы на способность подавлять активность CYP17A1, 3b-HSD и 17b-HSD3.…”

Section: производные и аналоги абиратерона и галетеронаunclassified

Steroidal Inhibitors of CYP17A1 as a Template For Novel Anti-Cancer Agents Development

Latysheva

Misharin

2018

BMCRM

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This review deals with studies of researches of novel CYP17A1 steroidal inhibitors and relative compounds published over the last ten years. The review contains six chapters in which novel targets of well-known CYP17A1 inhibirors (abiraterone and galeterone), anti-cancer and anti-proliferative activities of them major metabolites and new synthetic analogs, and in addition another nitrogen-containing androstane and pregnane derivatives are considered. In the review 354 structures of novel steroid derivatives and them anti-cancer efficiency data are considered. Analysis of the literature data allows us to consider steroidal inhibitors of CYP17A1 as multi-target anti-cancer agents with high pharmacological potential.

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“…Steroids have showed various biological activities including anti-tumor and antiproliferative effects on cells [1][2][3][4][5] and anti-flu virus effects [6]. Very recently it was reported that some new steroids could also be used as potential antileukemic agents [7] and 5α-reductase inhibitors [8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of 3-butyryloxy-16-(a#946;-naphthylmethylene)-5a#945;-androstane-17-one

Li¹,

Li²,

J³

et al. 2016

Proceedings of the 2016 International Conference on Biomedical and Biological Engineering

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Abstract. 3-Butyryloxy-16-(β-naphthylmethylene)-5α-androstane-17-one, a novel androstanone derivative, was synthesized by aldol condensation between epiandrosterone and β-naphthaldehyde and subsequent esterification reaction. The structure of the new product was characterized by 1 H NMR, 13 C NMR, IR, UV and mass spectra. The new compound may have potentia l application as anti-cancer agent and/or 5α-reductase inhibitor.

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Synthesis of methoxycarbonylpyrazolylandrostene derivatives, and their potential inhibitory effect on androgen biosynthesis and cell proliferation

Cited by 17 publications

References 34 publications

Design, Synthesis and Anticancer Activity of Novel Steroidal Derivatives with D‐Ring Fused or Substituted N‐Heterocyclic Systems

Design, Synthesis and Anticancer Activity of Novel Steroidal Derivatives with D‐Ring Fused or Substituted N‐Heterocyclic Systems

Steroidal Inhibitors of CYP17A1 as a Template For Novel Anti-Cancer Agents Development

Synthesis and Characterization of 3-butyryloxy-16-(a#946;-naphthylmethylene)-5a#945;-androstane-17-one

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