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Acta Pharmaceutica, Vol. 56 No. 2, 2006.

Izvorni znanstveni članak

Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as 5alpha-reductase inhibitors

ABD EL-GALIL EL-SAYED AMR
NEHAD AHMED ABDEL-LATIF
MOHAMED MOSTAFA ABDALLA

Puni tekst: engleski, pdf (113 KB) str. 203-218 preuzimanja: 1.016* citiraj
APA 6th Edition
EL-SAYED AMR, A.E., ABDEL-LATIF, N.A. i ABDALLA, M.M. (2006). Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as 5alpha-reductase inhibitors. Acta Pharmaceutica, 56 (2), 203-218. Preuzeto s https://hrcak.srce.hr/4556
MLA 8th Edition
EL-SAYED AMR, ABD EL-GALIL, et al. "Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as 5alpha-reductase inhibitors." Acta Pharmaceutica, vol. 56, br. 2, 2006, str. 203-218. https://hrcak.srce.hr/4556. Citirano 24.03.2019.
Chicago 17th Edition
EL-SAYED AMR, ABD EL-GALIL, NEHAD AHMED ABDEL-LATIF i MOHAMED MOSTAFA ABDALLA. "Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as 5alpha-reductase inhibitors." Acta Pharmaceutica 56, br. 2 (2006): 203-218. https://hrcak.srce.hr/4556
Harvard
EL-SAYED AMR, A.E., ABDEL-LATIF, N.A., i ABDALLA, M.M. (2006). 'Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as 5alpha-reductase inhibitors', Acta Pharmaceutica, 56(2), str. 203-218. Preuzeto s: https://hrcak.srce.hr/4556 (Datum pristupa: 24.03.2019.)
Vancouver
EL-SAYED AMR AE, ABDEL-LATIF NA, ABDALLA MM. Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as 5alpha-reductase inhibitors. Acta Pharm. [Internet]. 2006 [pristupljeno 24.03.2019.];56(2):203-218. Dostupno na: https://hrcak.srce.hr/4556
IEEE
A.E. EL-SAYED AMR, N.A. ABDEL-LATIF i M.M. ABDALLA, "Synthesis of some new testosterone derivatives fused with substituted pyrazoline ring as 5alpha-reductase inhibitors", Acta Pharmaceutica, vol.56, br. 2, str. 203-218, 2006. [Online]. Dostupno na: https://hrcak.srce.hr/4556. [Citirano: 24.03.2019.]

Sažetak
Condensation of 3β-hydroxy-16-[(4-chlorophenyl)methylene]androst-5-en-17-one 1 with hydrazine hydrate in acetic acid afforded N-acetyl pyrazoline derivative 2, while, condensation of 1 with semicarbazide afforded compound 3. Also, compound 1 was treated with hydrazine hydrate in absolute methanol or ethanol to afford the corresponding -methoxy (4) and -ethoxy (5) derivatives, which were cyclized with etherated boron trifluoride to the pyrazoline derivative 6. The later could be prepared directly by refluxing of 1 with hydrazine hydrate in dioxane. Oxidation of compound 6 with Oppenour or Moffat oxidizing agents yielded 3-oxo-derivatives 7 and 8, respectively. On the other hand, condensation of compound 1 with substituted hydrazines, gave the corresponding 3beta-hydroxyandrostenopyrazolines 9a,b, which were oxidized using Moffat method give 3-oxo-androstenopyrazolines 10a,b, which were condensed with ethylene triphenyl-phosphorane in DMSO to yield 3-ethylene androstenopyrazolines 11a,b. Dehydrogenation of 9a,b with Wettestein oxidation afforded 4,6-diene-3-one analogues 12a,b, which were treated with chloranil to yield delta4,6,8(14)-triene-3-one analogues 13a,b. Oppenour oxidation of 9a,b afforded Δ4-ene-3-one analogues 14a,b, which were treated with dichlorodicyanoquinone (DDQ) in dioxane to give Δ1,4,6-triene-3-one analogues 15a,b. Pharmacological screening showed that many of these compounds exhibit 5alpha-reductase activity.

Ključne riječi
testosterone; pyrazolines; Moffat oxidation; 5alpha-reductase inhibitor

Hrčak ID: 4556

URI
https://hrcak.srce.hr/4556

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