New steroidal oxazolines, benzoxazoles and benzimidazoles related to abiraterone and galeterone

Latysheva, Alexandra S.; Zolottsev, Vladimir A.; Veselovsky, A. V.; Scherbakov, Kirill A.; Morozevich, G. E.; Pokrovsky, Vadim S.; Новиков, Роман А.; Timofeev, Vladimir P.; Tkachev, Yaroslav V.; Misharin, A. Yu.

doi:10.1016/j.steroids.2019.108534

Cited by 17 publications

(14 citation statements)

References 43 publications

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“…The key intermediates were aminomethyl alcohols 66 and 67, which upon reaction with triphosgene, or with an alkyl/aryl isothiocyanate, followed by a cyclization, furnished title heterocyclic scaffolds (Scheme 9). In 2020, new oxazoline, benzoxazole, and benzimidazole derivatives were synthesized from 3βacetoxyandrosta-5,16-dien-17-carboxylic, 3β-acetoxyandrost-5-en-17β-carboxylic and 3β-acetoxypregn-5-en-21-oic acids by Pokrovsky et al 36 Scheme 10. Synthesis of oxazoline derivative 82.…”

Section: Scheme 7 Synthesis Of Oxazoline Derivatives 54 and 55mentioning

confidence: 99%

Recent syntheses of steroidal oxazoles, oxazolines and oxazolidines

Bendif¹,

Ibrahim‐Ouali²,

Dumur³

2021

Arkivoc

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Section: Scheme 7 Synthesis Of Oxazoline Derivatives 54 and 55mentioning

confidence: 99%

Recent syntheses of steroidal oxazoles, oxazolines and oxazolidines

Bendif¹,

Ibrahim‐Ouali²,

Dumur³

2021

Arkivoc

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“…Abiraterone and galeterone are commonly used drugs for prostate cancer [93,94]. So eight noble oxazoline, benzoxazole, and benzimidazole compounds [95] (Fig. 50) were prepared from 3β-acetoxyandrosta-5,16-dien-17-carboxylic, 3β-acetoxyandrost-5-en-17β-carboxylic, and 3βacetoxypregn-5-en-21-oic acids.…”

Section: Benzoxazole-steroid Derivativementioning

confidence: 99%

Anticancer activity of benzoxazole derivative (2015 onwards): a review

Ghoshal

Patel

2020

Futur J Pharm Sci

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Background According to the report published recently by the World Health Organization, the number of cancer cases in the world will increase to 22 million by 2030. So the anticancer drug research and development is taking place in the direction where the new entities are developed which are low in toxicity and are with improved activity. Benzoxazole and its derivative represent a very important class of heterocyclic compounds, which have a diverse therapeutic area. Recently, many active compounds synthesized are very effective; natural products isolated with benzoxazole moiety have also shown to be potent towards cancer. Main text In the last few years, many research groups have designed and developed many novel compounds with benzoxazole as their backbone and checked their anticancer activity. In the review article, the recent developments (mostly after 2015) made in the direction of design and synthesis of new scaffolds with very potent anticancer activity are briefly described. The effect of various heterocycles attached to the benzoxazole and their effect on the anticancer activity are thoroughly studied and recorded in the review. Conclusion These compiled data in the article will surely update the scientific community with the recent development in this area and will provide direction for further research in this area.

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“…During the development of new inhibitors of CYP17A1, a large number of androstane and pregnane derivatives have been introduced containing pyridyl-, picolidine-, pyrazolyl-, imidazolyl-, triazolyl-, isoxazolinyl-, dihydrooxazolinyl-, tetrahydrooxazolinyl-, benzimidazolyl-, and carbamoyl- substituents, mainly in positions 16, 17, and 22 [ 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ]. Galeterone, the most advanced among them and having a multiple mechanism of action, has reached phase III clinical trials [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Isoxazolyl Steroids as Anti-Prostate Cancer Agents

Rudovich

Peřina

Krech

et al. 2022

IJMS

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Steroids with a nitrogen-containing heterocycle in the side chain are known as effective inhibitors of androgen signaling and/or testosterone biosynthesis, thus showing beneficial effects for the treatment of prostate cancer. In this work, a series of 3β-hydroxy-5-ene steroids, containing an isoxazole fragment in their side chain, was synthesized. The key steps included the preparation of Weinreb amide, its conversion to acetylenic ketones, and the 1,2- or 1,4-addition of hydroxylamine, depending on the solvent used. The biological activity of the obtained compounds was studied in a number of tests, including their effects on 17α-hydroxylase and 17,20-lyase activity of human CYP17A1 and the ability of selected compounds to affect the downstream androgen receptor signaling. Three derivatives diminished the transcriptional activity of androgen receptor and displayed reasonable antiproliferative activity. The candidate compound, 24j (17R)-17-((3-(2-hydroxypropan-2-yl)isoxazol-5-yl)methyl)-androst-5-en-3β-ol, suppressed the androgen receptor signaling and decreased its protein level in two prostate cancer cell lines, LNCaP and LAPC-4. Interaction of compounds with CYP17A1 and the androgen receptor was confirmed and described by molecular docking.

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New steroidal oxazolines, benzoxazoles and benzimidazoles related to abiraterone and galeterone

Cited by 17 publications

References 43 publications

Recent syntheses of steroidal oxazoles, oxazolines and oxazolidines

Recent syntheses of steroidal oxazoles, oxazolines and oxazolidines

Anticancer activity of benzoxazole derivative (2015 onwards): a review

Synthesis and Biological Evaluation of New Isoxazolyl Steroids as Anti-Prostate Cancer Agents

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