Total synthesis of steroids and heterosteroids from BISTRO

Ibrahim‐Ouali, Malika

doi:10.1016/j.steroids.2015.02.014

Cited by 13 publications

(11 citation statements)

References 131 publications

(142 reference statements)

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“…There are also many excellent reviews in the literature, which are devoted to the biological role and functions of organoselenium compounds [301][302][303][304]. Apparently, selena steroids are the main group of the essential metalloids that have been synthesized over the past 50 years, and approximately 300 have been synthesized [304][305][306][307][308][309].…”

Section: Bioactive Selena Steroidsmentioning

confidence: 99%

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In Silico Prediction of Steroids and Triterpenoids as Potential Regulators of Lipid Metabolism

Dembitsky

2021

Marine Drugs

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This review focuses on a rare group of steroids and triterpenoids that share common properties as regulators of lipid metabolism. This group of compounds is divided by the type of chemical structure, and they represent: aromatic steroids, steroid phosphate esters, highly oxygenated steroids such as steroid endoperoxides and hydroperoxides, α,β-epoxy steroids, and secosteroids. In addition, subgroups of carbon-bridged steroids, neo steroids, miscellaneous steroids, as well as synthetic steroids containing heteroatoms S (epithio steroids), Se (selena steroids), Te (tellura steroids), and At (astatosteroids) were presented. Natural steroids and triterpenoids have been found and identified from various sources such as marine sponges, soft corals, starfish, and other marine invertebrates. In addition, this group of rare lipids is found in fungi, fungal endophytes, and plants. The pharmacological profile of the presented steroids and triterpenoids was determined using the well-known computer program PASS, which is currently available online for all interested scientists and pharmacologists and is currently used by research teams from more than 130 countries of the world. Our attention has been focused on the biological activities of steroids and triterpenoids associated with the regulation of cholesterol metabolism and related processes such as anti-hyperlipoproteinemic activity, as well as the treatment of atherosclerosis, lipoprotein disorders, or inhibitors of cholesterol synthesis. In addition, individual steroids and triterpenoids were identified that demonstrated rare or unique biological activities such as treating neurodegenerative diseases, Alzheimer’s, and Parkinson’s diseases with a high degree of certainty over 95 percent. For individual steroids or triterpenoids or a group of compounds, 3D drawings of their predicted biological activities are presented.

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Section: Bioactive Selena Steroidsmentioning

confidence: 99%

“…Tellura steroids are a rare group of organic synthetic compounds whose biological activity is of great interest for medicine, pharmacology, and the pharmaceutical industry [304,306,308,309,311]. The chemical structures of steroids and triterpenoids are shown in Figure 27, and the biological activity is shown in Table 12.…”

Section: Bioactive Tellura Steroidsmentioning

confidence: 99%

In Silico Prediction of Steroids and Triterpenoids as Potential Regulators of Lipid Metabolism

Dembitsky

2021

Marine Drugs

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“…Terpenoid alkaloids and aza-steroids make up a captivating class of such biorelevant ring-fused azacycles. Indeed, the former is an intriguing skeleton of natural compounds that arise from the incorporation of a nitrogen atom during the biosynthetic process mediated by cyclases . However, some of these compounds are still elusive from the synthetic perspective, and therefore, new methodologies are highly desirable, especially by exploiting the rapid stereoselective forging performance peculiar to the biomimetic cyclization reactions.…”

Section: Introductionmentioning

confidence: 99%

Iridium Acylnitrenoid-Initiated Biomimetic Cascade Cyclizations: Stereodefined Access to Polycyclic δ-Lactams

Tufano,

Lee,

Barilli

et al. 2023

J. Am. Chem. Soc.

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Ring-fused azacyclic compounds are important building units in the synthesis of biorelevant natural products, pharmaceutical agents, and molecular materials. Herein, we present a new approach to these condensed azacycles by a biomimetic cascade cyclization of arylalkenyl dioxazolones. This cascade reaction was found to proceed with excellent stereoselectivity and a high functional group tolerance. The substrate scope of arylalkenyl dioxazolones turned out to be highly flexible and extendable to additional terminating subunits, such as heteroaryl and alkynyl moieties. This biomimetic cyclization was elucidated to be initiated by an intramolecular transfer of the in situ generated electrophilic Ir-acylnitrenoid to the tethered olefinic double bond, leading to a key N-acylaziridine intermediate, which is in turn reacted with pendant (hetero)arenes or alkynes in a highly regio- and stereoselective manner to produce ring-fused azacyclic compounds.

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“…Steroids constitute an extensive and important class of biologically active polycyclic compounds that are widely used for therapeutic purposes. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Even after decades of research, the total synthesis of steroid nuclei by improved strategies continues to receive considerable attention. Numerous methods [21][22][23][24][25][26][27] have been exploited for the total synthesis of steroids which are widely distributed in nature, and which possess practical medical importance.…”

Section: Introductionmentioning

confidence: 99%

A short review on selena and tellurasteroids

Ibrahim‐Ouali¹,

Dumur²

2022

Arkivoc

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Recently hetero steroids have received much attention for pharmacological interest. Indeed, the replacement of one or more carbon atoms of a steroid molecule by a heteroatom often results in useful alterations to its biological activity because this modification affects the chemical properties of this steroid. Compounds containing a selenium, or a tellurium atom can possess biological properties and so have a great potential for the creation of a new library of molecules important for biological applications. Some of them have been used as antibacterial, antiviral, antihypertensive, or chemopreventive anticancer agents. Recent developments in the syntheses of selena and tellurasteroids are described herein.

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Total synthesis of steroids and heterosteroids from BISTRO

Cited by 13 publications

References 131 publications

In Silico Prediction of Steroids and Triterpenoids as Potential Regulators of Lipid Metabolism

In Silico Prediction of Steroids and Triterpenoids as Potential Regulators of Lipid Metabolism

Iridium Acylnitrenoid-Initiated Biomimetic Cascade Cyclizations: Stereodefined Access to Polycyclic δ-Lactams

A short review on selena and tellurasteroids

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