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.Kondenzacijom 3β-hidroksi-16-[(4-klorofenil)metilen]androst-5-en-17-ona 1 s hidrazin hidratom u octenoj kiselini dobiven je derivat N-acetil pirazolina 2, a kondenzacijom 1 sa semikarbazidom priređen je spoj 3. Reakcijom spoja 1 s hidrazin hidratom u apsolutnom metanolu ili etanolu nastali su odgovarajući -metoksi (4) i -etoksi (5) derivati, koji su ciklizirani s borovim trifluoridom u derivat pirazolina 6. Isti spoj se može pripaviti izravno refluksiranjem spoja 1 s hidrazin hidratom u dioksanu. Oksidacijom spoja 6 s Oppenourovim ili Moffatovim oksidansom dobiveni su 3-okso derivati 7, odnosno 8. S druge strane, kondenzacija spoja 1 sa supstituiranim hidrazinima dala je odgovarajuće 3beta-hidroksiandrostenopirazoline 9a,b, koji su oksidirani Moffatovom metodom u 3-okso-androstenopirazoline 10a,b. Ovi produkti su dalje kondenzirani s etilen rifenil-fosforanom u DMSO u 3-etilen androstenopirazoline 11a,b. Wettesteinovom dehidrogenacijom 9a,b dobiveni su delta4,6-dien-3-on analozi 12a,b, koji su s kloranilom dali 4,6,8(14)-trien-3-on analoge 13a,b. Oppenourovom oksidacijom 9a,b dobiveni su Δ4-en-3-on analozi 14a,b, koji su s diklorodicianokinonom (DDQ) u dioksanu dali Δ1,4,6-trien-3-on analoge 15a,b. Farmakološka ispitivanja ukazuju da mnogi od sintetizirnih spojeva inhibiraju 5alfa-reduktazu
