Adrenal Hormones and Related Compounds. V. Fluorinated 6-Methyl Steroids

Abstract

Communications to the Editor 1515 showed almost no activity as the amide donor.Under the conditions of the experiment shown in Table II, glutamine supply limits DPN synthesis.Thus, in a separate experiment under similar conditions, with NA held constant at 10 /¿moles per vessel, DPN synthesis in the presence of 0, 4, 10 and 20 µ of glutamine was 0.052, 0.104, 0.172 and 0.274 µ , respectively. Further investigations are in progress seeking to elucidate the mechanism of pyridine nucleotide synthesis from nicotinic acid and its amide.

Corticosteroids: A boon or bane for COVID-19 patients?

“…The resultant epoxide is then treated with MeMgBr, and the ketal protection is then removed by Zn/H 2 SO 4 reduction, yielding the 5-hydroxy-6-methyl dihydrocortisone derivative 7.3 . The resultant hydroxyketone 7.3 is dehydrated in alkaline condition, and then the product 6-methylcortisone is further microbiologically dehydrogenated at the C1-C2 position to get the required methylprednisolone [76] , [77] , [78] .

Scheme 7 Synthesis of methyl prednisolone from hydrocortisone.

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Fluorine-Containing Steroids

“…f) 6a-Methoxy Addition of this group to 9a-fluoroprednisolone resulted in lowered thymolytic activity, the derivative being only one-fourth as potent as cortisol, and producing no sodium retention (HELLER and BERNSTEIN, 1961). g) 6a-Methyl SPERO et al (1957) synthesized 6a-methyl substituted steroids containing also 9a-fluoro or 21-fluoro groups. The 6a-methyl steroids characteristically produced little sodium retention, but were very active in anti-inflammatory and glucocorticoid assays.…”

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

“…[«]d +72°; £ 240-246 and 280-288 Acetylation of Via with an excess of acetic anhydride in pyridine solution at room temperature for 18 X, 3.19; O, 16.43. (e) Potassium cyanide (20 g.) was added to a solution of pregnenolone acetate epoxide (Ilia) in ethylene glycol (600 cc.)…”