Notes- Steroids. II. 4-Aza-5-cholesten-3-one and 4-Aza-5-pregnene-3,20-dione

Doorenbos, Norman J.; Huang, Chien Li; Tamorria, C. Richard.; Wu, M. T.

doi:10.1021/jo01351a613

Cited by 14 publications

(3 citation statements)

References 3 publications

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“…Compound l c was assumed to have the 20P configuration (14) as it was obtained by the sodium borohydride reduction of the 20-keto group of 4-aza-5a-pregnan-3,20-dione, prior to acetylation and dehydrogenation with benzeneseleninic anhydride. Enarnide 5 was prepared according to a literature procedure (15). NCS and TCIA were obtained from the Aldrich Co. and were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

The synthesis of some novel N-chloro-Δ¹-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid

Back¹,

Chau²,

Dyck³

et al. 1991

Can. J. Chem.

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The preparation of N-chloro-Δ1-4-azasteroids 2a–2c from lactams 1a–1c was achieved conveniently and in high yield with trichloroisocyanuric acid. The treatment of 20β-hydroxy-4-aza-5α-pregn-1-en-3-one (1d) with this reagent produced the less stable N-chloro compound 2d, which reacted further to afford 4-aza-5α-pregn-1-en-3,20-dione (4) as the principal product. The similar chlorination of 4-azacholest-5-en-3-one (5) occurred at C-6, giving 6-chloro-4-azacholest-5-en-3-one (6). Photolysis of N-chloro-4-aza-5α-cholest-1-en-3-one (2a) in methanol produced the transient N-acyl imine 7, which was trapped by the solvent to afford 5-methoxy-4-azacholest-1-en-3-one (8), along with 4-azacholesta-1,5-dien-3-one (9) and its 6-chloro derivative 10. Key words: N-chloroazasteroid, Δ1-4-azasteroid, N-chloro-Δ1-4-azasteroid, trichloroisocyanuric acid, N-chlorination.

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Section: Methodsmentioning

confidence: 99%

The synthesis of some novel N-chloro-Δ¹-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid

Back¹,

Chau²,

Dyck³

et al. 1991

Can. J. Chem.

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“…Steroids. Steroids prefixed with the letters ND were synthesized as previously reported (4)(5)(6)(7)(8)(9). (The synthesis of ND 164, ND 213, ND 497, and ND 595 has not been reported.)…”

Section: Methodsmentioning

confidence: 99%

Effect of Azasteroids on Gram-Positive Bacteria

1967

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A group of nitrogen-containing steroids closely related in structure was screened for antibacterial activity, by use of Bacillus subtilis and Sarcina lutea as the test organisms. The most active compounds were cholesterol derivatives containing a tertiary or quaternary nitrogen in, or attached to, the A ring. Similar methyltestosterone or progesterone derivatives were inactive. All of the cholesterol derivatives that inhibited growth were surfactant, and, structurally, they would be classified as cationic detergents. Some of the inactive compounds were surfactant, but, structurally, they would be classified as nonionic detergents. Certain features of the antibacterial activity of one of the active steroids-ND 212 (4-dimethylaminoethyl-4-aza-5-cholesten-3-one methiodide)-were studied. Growth of a culture of B. subtilis containing 5 X 107 cells per milliliter was inhibited by 1 Ag/ml (1.7 x 10-6 M) of ND 212. The amount of growth inhibition was directly related to both cell and steroid concentration. Loss of viability was rapid and irreversible. With B. subtilis, cell lysis was observed. With S. lutea grown in C'4-glucose, ND 212 caused release into the media of up to 25 % of the cellular radioactivity. Extensive leakage occurred before loss of viability was observed. At bacteriostatic azasteroid concentrations, there was little leakage. ND 212 was readily bound in large amounts to B. subtilis cells. Inactive azasteroids were bound poorly. C'4-cholestanone was also bound, whereas C'4-methyltestosterone and C'4-progesterone were not bound in significant amounts. At least 50% of the bound C'4-cholestanone was associated with the membrane fraction. Smith, Shay, and Doorenbos (22) were the first to report antimicrobial properties of steroids containing nitrogen in the nucleus. The compounds, 4-aza-cholestanes, inhibited the growth of various gram-positive bacteria, yeasts, and molds. The growth of gram-negative bacteria was not inhibited. Further studies by the same authors have delineated certain features of the mechanism of action of the compounds. The azacholestanes were found to be lethal to microorganisms (22) and to be surfactant (23). The authors concluded that there was no positive relationship between surface activity and antimicrobial activity (23). More recently, the compounds have been found to cause lysis of protoplasts of Sarcina lutea (21) and loss of cellular consitutents from yeast (R. F. Smith, Ph.D. Thesis, Univ. Maryland, College Park, 1965), suggesting that their primary site of action is the cytoplasmic membrane.

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“…Nevertheless, dihydroxyfluorene XVHI was reduced with copper-chromium oxide at 210°. Even under these relatively mild (8) E. H. Huntress and I. S. Cliff, J. Am.…”

Section: VIII Ixmentioning

confidence: 99%

Syntheses Related to Etiojervane. II. Synthesis of Some Substituted Fluorenes

Barnes¹,

Faessinger²

1961

J. Org. Chem.

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Notes- Steroids. II. 4-Aza-5-cholesten-3-one and 4-Aza-5-pregnene-3,20-dione

Cited by 14 publications

References 3 publications

The synthesis of some novel N-chloro-Δ¹-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid

The synthesis of some novel N-chloro-Δ¹-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid

Effect of Azasteroids on Gram-Positive Bacteria

Syntheses Related to Etiojervane. II. Synthesis of Some Substituted Fluorenes

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Notes- Steroids. II. 4-Aza-5-cholesten-3-one and 4-Aza-5-pregnene-3,20-dione

Cited by 14 publications

References 3 publications

The synthesis of some novel N-chloro-Δ1-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid

The synthesis of some novel N-chloro-Δ1-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid

Effect of Azasteroids on Gram-Positive Bacteria

Syntheses Related to Etiojervane. II. Synthesis of Some Substituted Fluorenes

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The synthesis of some novel N-chloro-Δ¹-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid

The synthesis of some novel N-chloro-Δ¹-4-azasteroids by efficient N-chlorination of azasteroid lactams with trichloroisocyanuric acid