Some New Active Corticosteroids

Gould, David; Shapiro, Elliot L.; Herzog, Hersfel L.; Gentles, Margaret Jevnik; Hershberg, E. B.; Charney, William; Gilmore, Marilyn; Tolksdorf, Sibylle; Eisler, Milton; Perlman, Preston L.; Pechet, Maurice M.

doi:10.1021/ja01559a074

Cited by 16 publications

(6 citation statements)

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“…Recently we reported the partial purification and certain properties of a multi-enzyme system of sheep liver concerned with the conversion of citrovorum factor (N5-formyltetrahydrofolic acid) to a serine aldolase cofactor.2 Subsequent investigations have enabled us to separate an enzyme from sheep liver acetone powders which converts citrovorum factor to a compound with an absorption spectrum similar to that of anhydrocitrovorum factor (anhydroleucovorin, N6'10-methyltetrahydrofolic acid). The enzyme was prepared by passing an aqueous extract of the acetone powder through an hydroxylapatite column (the aqueous eluate contained the enzyme) or by adsorption of the aqueous acetone powder extract on calcium phosphate gel (gelrprotein ratio 1.2 or more; protein (1) Taken in part from a dissertation submitted by James M.…”

Section: Introductionmentioning

confidence: 99%

Citrovorum Factor Cyclodehydrase¹

Peters¹,

Greenberg²

1958

J. Am. Chem. Soc.

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Section: Introductionmentioning

confidence: 99%

Citrovorum Factor Cyclodehydrase¹

Peters¹,

Greenberg²

1958

J. Am. Chem. Soc.

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“…[3][4][5] a-Bromoketones of steroidal hormones are utilized to lead to various unsaturated ketone derivatives. 3,[6][7][8] Although many investigations involving brominations of steroidal ketones, including kinetically controlled studies, [9][10][11] have been reported, only a few reports have described the bromination of steroidal hormones having an a,b-unsaturated ketone. Djerassi et al 12) reported that the bromination of 17-Oacetyltestosterone (1) (17b-acetoxyandrost-4-en-3-one) with bromine in AcOH-Et 2 O gave a mixture of 2a,6b-(2) and 2a,6a-dibromo-17b-acetoxyandrost-4-en-3-one (3) in 80-82% yields.…”

mentioning

confidence: 99%

Brominations of Steroidal Hormone Having .ALPHA.,.BETA.-Unsaturated Ketone, 17-O-Acetyltestosterone, in the Presence of Silver Triflate.

Shimizu

Tobari

Koyanagi

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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Bromination of 17-O-acetyltestosterone (17b b-acetoxyandrost-4-en-3-one) (1) was performed with 1, 5, and 10 eq of Br 2 in AcOH-Et 2 O at room temperature. In all cases 2a a,6b b-(2) and 2a a,6a a-dibromo-17b b-acetoxyandrost-4-en-3-one (3) were obtained, although the yields were dependent upon the conditions used. Bromination of compound 1 with 10 eq of Br 2 in the presence of silver trifluoromethanesulfonate (silver triflate, AgOTf) at room temperature for 12 h gave 2,7a a-dibromo-(4) and 2,4,7a a-tribromo-17b b-acetoxy-3-hydroxy-1-methylestra-1,3,5(10)-triene-6-one (5). The formations of the products were inferred on the basis of products obtained under controlled brominations of 1 in the presence of AgOTf, and of those obtained by the brominations of compounds 9-13 also in the presence of AgOTf.

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“…Treatment of the epoxide (2) with hydrobromic acid followed by reaction with zinc and ethanol gave the 7a-hydroxy-derivative (3). Attempts to prepare the 17-ethylene acetal derivative of compound (3) by heating a solution of the ketone (3) with ethylene glycol and toluenep-sulphonic acid in benzene resulted, however, in the elimination of the 7a-hydroxy-group and compound (4) was obtained. We then investigated an alternative method which was successful (Scheme).…”

mentioning

confidence: 99%