Preparation and progestational activity of 6-cyano-16-methylene-17.alpha.-hydroxy-4,6-pregnadiene-3,20-dione 17-acetate and related compounds

Popper, T. L.; Faro, Hans P.; Carlon, F. E.; Herzog, Hershel L.

doi:10.1021/jm00275a033

Cited by 4 publications

(3 citation statements)

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“…The synthetic compounds 17α-aza-3-cyanosteroid with a phenyl substituent on the nitrogen (48) and 17-aza-17α-homo-3-cyano-androst-3,5-en-16,17α-dione (49) exhibited moderate inhibition of 5α-reductase type II [79]. 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].…”

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

confidence: 99%

“…The second group consists of anabolic steroids featuring a nitro group in the third position (62)(63)(64)(65)(66)(67)(68)(69)(70)(71). The third group encompasses steroids, with a nitro group in the fourth position (72)(73)(74)(75)(76)(77)(78)(79)(80)(81). The fourth group includes steroids, where the nitro group is in the sixth position (82)(83)(84)(85)(86)(87)(88)(89)(90), as shown in Figure 10, with their biological activity presented in Table 4.…”

Section: Steroids Bearing Nitro Groupmentioning

confidence: 99%

“…The 4-substituted estrones, as well as a series of 6α-and 6β-substituted estrones, have been identified as aromatase inhibitors [122]. Several 4-nitrosteroids (72)(73)(74)(75)(76)(77)(78)(79)(80)(81), including compounds like 20,21-dihydroxy-4-nitropregn-4-en-3-one (78) and 17β-cyclopropyloxy-4-nitroandrost-4-en-3-one (80), exhibit aromatase inhibitory activity, as well as inhibition of steroid C17-20 lyase and 5α-reductase [123]. Three 4-nitrosteroids (78-80, 3D graph is shown in Figure 13) were synthesized and identified as potential inhibitors of 4-methyl sterol oxidase [124].…”

Section: Steroids Bearing Nitro Groupmentioning

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

confidence: 99%

Section: Steroids Bearing Nitro Groupmentioning

confidence: 99%

Section: Steroids Bearing Nitro Groupmentioning

confidence: 99%

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Steroids Bearing Heteroatom as Potential Drugs for Medicine

Dembitsky

2023

Biomedicines

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The Vilsmeier Reaction of Non‐Aromatic Compounds

Jones

Stanforth

2000

Organic Reactions

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This chapter extends the discussion to reactions between the Vilsmeier‐Haack reagent (subsequently referred to as the Vilsmeier reagent for brevity) and any other compounds in which a carbon‐carbon bond is formed. The discussion thus excludes reactions in which the Vilsmeier reagent acts as a chlorinating agent (for example in the preparation of acid chlorides), or in which it forms carbon‐oxygen or carbon‐nitrogen bonds, unless these are accompanied by formation of a carbon‐carbon bond. For a discussion of the nature of the reagent and of the mechanism of the reaction, the earlier chapter in vol. 49 should be consulted. There are also a number of reviews that deal at length with mechanisms of reactions involving the Vilsmeier reagent, notably those by Jutz and Marson, and hence this chapter will concentrate on applications, with brief mention of mechanisms when necessary. Wizinger has pointed out that alkenes could react with the Vilsmeier reagent, but his only examples were styrenes where the intermediate carbocation has considerable stability. Hydrolysis gives the cinnamaldehyde. In principle, any alkene which is not too sterically hindered can undergo this reaction, but the Vilsmeier reagent has low reactivity as an electrophile, and in practice activation is often necessary. The addition depends on the HOMO of the alkene, and anything increasing the HOMO energy will aid reaction, as for example further conjugation (dienes, trienes, etc.) or the presence of an electron‐donating substituent. Hence aldehydes and ketones are active in their enol forms, and enol ethers and enamines are good substrates. Indeed, all additions covered by this chapter can be regarded as alkene additions, even those on active methyl groups attached to electron‐deficient rings. As with any reaction involving carbocation intermediates, rearrangements are possible; the initial products are sometimes enamines, and this can give rise to polysubstitution. The substrates are grouped into eleven major subsections; references to reviews of particular relevance will be found in the appropriate subsection.

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Transformations of Carbocycles

2010

Name Reactions for Carbocyclic Ring Formations

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Preparation and progestational activity of 6-cyano-16-methylene-17.alpha.-hydroxy-4,6-pregnadiene-3,20-dione 17-acetate and related compounds

Cited by 4 publications

References 1 publication

Steroids Bearing Heteroatom as Potential Drugs for Medicine

Steroids Bearing Heteroatom as Potential Drugs for Medicine

The Vilsmeier Reaction of Non‐Aromatic Compounds

Transformations of Carbocycles

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