6-Chloro-6-dehydro-A-nor Steroids with Progestational Activity. 7α-Chloro-A-nor Steroids

Diassi, Patrick A.; Levine, Seymour D.; Palmere, Raymond M.

doi:10.1021/jm00316a011

Cited by 7 publications

(3 citation statements)

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“…Indeed, for 4,6-dien-3-ones it has been stated that they are formed in solution but are too unstable to isolate. 14,16 In contrast, 6,7-dehydro-A-nortestosterone is reported16 to form an adduct, the 7«-chIoro compound, with HC1. Its stability is attributed16 to the difficulty in forming the 7a-chloro-3.5-dien-3-ol necessary for elimination to the 6,7-dehydro compound.…”

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Synthesis and structure-activity studies in a series of 7.alpha.-halogeno corticosteroids

Shue¹,

Green²,

Berkenkoph³

et al. 1980

J. Med. Chem.

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The preparation and topical antiinflammatory potencies of a series of 7 alpha-halogeno-16-substituted-prednisolone derivatives are described. The 7 alpha-chloro, 7 alpha-bromo, and 7 alpha-iodo corticosteroids were obtained by addition of hydrogen halide to the 6,7-dehydro compounds. The extent of addition of HCl varied with substitution at C-11, while no addition of HF was observed at all. The 7 alpha-fluoro corticosteroids were prepared by reaction of the appropriate 7 beta-hydroxy compounds with N,N-diethyl(2-chloro-1,1,2-trifluoroethyl)amine. The 7 beta-hydroxy steroids were obtained, in turn, from the 6,7-dehydro compounds via the 6 beta,7 beta-dihydroxy derivatives. Antiinflammatory potencies were measured in mice by the Tonelli croton oil ear assay. The greatest effect of a 7 alpha-halogen was observed in the 16 alpha-methylprednisolone series, where 7 alpha-chloro and 7 alpha-bromo substitution increased potency 2.5- to 3.5-fold. Compounds 4b and 5b were equipotent to betamethasone dipropionate. 7 alpha-Halogen substitution in other series produced more variable effects and sometimes led to a reduction of antiinflammatory potency.

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“…Anal. (C16H2604) C, H. 4-Carboxy-4-cyclopentylcyclohexanone Ethylene Ketal (16). A mixture of 10.0 g (0.035 mol) of the ester and 2.10 g of NaOH in 80 mL of ethylene glycol was heated at reflux for 18 h. The mixture was worked up exactly as above and the product recrystallized (SSB) to give 7.22 g (51%) of acid, mp 110-113 °C.…”

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Synthesis and structure-activity studies in a series of 7.alpha.-halogeno corticosteroids

Shue¹,

Green²,

Berkenkoph³

et al. 1980

J. Med. Chem.

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“…After 5 min the solution was cooled and 320 mg of 8, mp 258-259°, was collected by filtration. The analytically pure material was obtained from the same solvent: mp 261-263°; [a]25D -419°; uv (EtOH) 311 nm (e 29,800);ir (CHCy 1730,1650,and 1610 cm"1; nmr (CDC13) 5.57 (s, 1 H, C6H), 5.29 (d, 1 H, C"H), and 3.68 (s, 3 H, Anal. (C24H32Os) C, H. 7-Chloro-30,17a-dihydroxy-5a-pregn-7-en-2O-one .…”

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confidence: 99%