Steroids. CXXIV.<sup>1</sup> Studies in Cyano Steroids. Part I. The Synthesis of a Series of C-6-Cyano Steroid Hormones

Bowers, A.; Denot, E.; Sánchez, María Blanca; Sánchez-Hidalgo, L. M.; Ringold, Howard J.

doi:10.1021/ja01528a053

Cited by 23 publications

(5 citation statements)

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“…Steroids that incorporate a nitrile group are referred to as cyanosteroids [41]. The synthesis of anabolic cyanosteroids was first accomplished during the 1940s-1950s [42][43][44]. Currently, over 400 cyanosteroids have been synthesized, demonstrating notable antibacterial, antifungal, and anticancer properties [45][46][47][48][49].…”

Section: Steroids Bearing Nitrile Groupmentioning

confidence: 99%

“…The synthesis of 6-cyano-16-methylene-17α-hydroxypregna-4,6-diene-3,20-dione 17-acetate (50) and its 3-OEt analog (51) has been described, but their biological activity has not been tested [80]. Various authors have synthesized several biologically active cyanosteroids and their derivatives (42)(43)(44)(45)(46)(47), although the extent of their activity evaluation is limited [81][82][83][84]. Additionally, carbon-bridged steroids of cyanosteroids (48, 49, and 50) and a rare dicyanosteroid (51) have been synthesized, yet their biological activity remains unstudied [85].…”

Section: The Influence Of Nitrile Group(s) Positioning In Steroids An...mentioning

confidence: 99%

“…Figure42. 3D graph illustrating the predicted and calculated activity of steroids bearing a selenium atom (244, 245, and 250) with a maximum confidence level exceeding 93%.…”

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confidence: 99%

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Steroids Bearing Heteroatom as Potential Drugs for Medicine

Dembitsky

2023

Biomedicines

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Heteroatom steroids, a diverse class of organic compounds, have attracted significant attention in the field of medicinal chemistry and drug discovery. The biological profiles of heteroatom steroids are of considerable interest to chemists, biologists, pharmacologists, and the pharmaceutical industry. These compounds have shown promise as potential therapeutic agents in the treatment of various diseases, such as cancer, infectious diseases, cardiovascular disorders, and neurodegenerative conditions. Moreover, the incorporation of heteroatoms has led to the development of targeted drug delivery systems, prodrugs, and other innovative pharmaceutical approaches. Heteroatom steroids represent a fascinating area of research, bridging the fields of organic chemistry, medicinal chemistry, and pharmacology. The exploration of their chemical diversity and biological activities holds promise for the discovery of novel drug candidates and the development of more effective and targeted treatments.

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Section: Steroids Bearing Nitrile Groupmentioning

confidence: 99%

Section: The Influence Of Nitrile Group(s) Positioning In Steroids An...mentioning

confidence: 99%

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Steroids Bearing Heteroatom as Potential Drugs for Medicine

Dembitsky

2023

Biomedicines

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“…styrene oxide [372]) the products readily dehydrate to yield a,b-unsaturated nitriles [373] (Scheme 4.86). Me 3 SiCN can also be used as reagent, but trimethylsilyl ethers will be the main products.…”

Section: Epoxide Opening By Cyanidementioning

confidence: 99%

Aliphatic Nucleophilic Substitutions: Problematic Electrophiles

Dörwald

2004

Side Reactions in Organic Synthesis

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Nucleophilic substitutions at sp 3 -hybridized carbon are among the most useful synthetic transformations, and have been thoroughly investigated [1][2][3]. The success of these reactions depends mainly on the structures of the nucleophile and electrophile, their concentration, and on the solvent and reaction temperature chosen. The structure of the electrophile in nucleophilic substitutions is of critical importance, because many unwanted side reactions result from unexpected reactivity of the electrophile.In Scheme 4.1 the mechanisms of typical monomolecular (Sn1) and bimolecular (Sn2) nucleophilic substitutions at a neutral electrophile with an anionic nucleophile are sketched. Sn1 reactions usually occur when the electrophile is sterically

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“…The epoxides 6 (1.1 g, 0.0067 mol) and NaCN (1.1 g, 0.022 mol) were heated to 60°in ethylene glycol (30 ml) for 24 hr. 8 The mixture was poured into H20 and extracted with EtOAc. The extract was washed and dried and the product 7 (1.08 g, 84% yield; ir 3400, 2200 cm-1) was dissolved in dry CgHe (15 ml) and thionyl chloride (1 ml) was added; the mixture was refluxed for 1 hr and then evaporated to dryness.…”

Section: Active2mentioning

confidence: 99%