YU60496A - New 16,17 -seco-16-ceto-i 16 oxymino-17-substituted stereoides of extratrienes and androstenic serial with biological activity - Google Patents
New 16,17 -seco-16-ceto-i 16 oxymino-17-substituted stereoides of extratrienes and androstenic serial with biological activityInfo
- Publication number
- YU60496A YU60496A YU60496A YU60496A YU60496A YU 60496 A YU60496 A YU 60496A YU 60496 A YU60496 A YU 60496A YU 60496 A YU60496 A YU 60496A YU 60496 A YU60496 A YU 60496A
- Authority
- YU
- Yugoslavia
- Prior art keywords
- substituted
- oximino
- keto
- group
- benzyl
- Prior art date
Links
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- Steroid Compounds (AREA)
Abstract
Pronalazak se odnosi na sintezu novih, biološki aktivnih 16,17-seko-, 16-keto- i 16-oksimino-17-supstituisanih steroida estronske i androstenske serije. Prema pronalasku se na 17-keto grupu odgovarajućih 17-keto-16-oksima vrši adicija RLi ili RMgJ, gde R predstavlja alkil sa 1-4 ugljenikova atoma, fenil, benzil ili pikolil ostatak, u tetrahidrofuranu. Dobijeni 16-oksimino-17-supstituisani estra-1,3,5(10)-trienski i 16-oksimino-17-supstituisani-5-androstenski derivati opšte formule II se ili dalje koriste kao intermedijeri u postupku ili kao nova biološki aktivna jedinjenja. Za dobijanje 16,17-seko-17-supstituisanih derivata, u obe serije, se derivati kod kojih je R1 oksimino grupa, podvrgavaju Beckman-ovoj fragmentaciji, pod dejstvom p-toluol sulfonilhlorida u piridinu, dok se 16-keto-17-supstituisani derviati, u obe serije, dobijaju samo kada je R benzil ili metil ostatak, hidrolizom 16-oksimino grupe u odgovarajuću keto grupu, delovanjem kiselim vodenim titantrihloridom, uz simultanu migraciju benzil, odnosno, metil grupe sa 17 α na 17 Гџ poziciju.The invention relates to the synthesis of novel, biologically active 16,17-seco-, 16-keto- and 16-oximino-17-substituted estrone and androstenic series steroids. According to the invention, the addition of RLi or RMgJ to the 17-keto group of the corresponding 17-keto-16-oximes is carried out, where R represents alkyl of 1-4 carbon atoms, phenyl, benzyl or picolyl residue, in tetrahydrofuran. The resulting 16-oximino-17-substituted ester-1,3,5 (10) -triene and 16-oximino-17-substituted-5-androstene derivatives of the general formula II are still used as intermediates in the process or as novel biologically active compounds . To obtain 16,17-sec-17-substituted derivatives, in both batches, derivatives of which R 1 is an oximino group are subjected to Beckman fragmentation under the action of p-toluene sulfonyl chloride in pyridine, while 16-keto-17-substituted dervates, in both batches, are obtained only when R is benzyl or methyl residue by hydrolysis of the 16-oximino group to the corresponding keto group, by the action of acidic aqueous titrant trichloride, with simultaneous migration of benzyl, or methyl, from 17 α to 17 Gj position.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YUP-604/96A RS49568B (en) | 1996-11-14 | 1996-11-14 | Substituted 16,17-secosteroids of estratrien and androsten seroes with biological activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YUP-604/96A RS49568B (en) | 1996-11-14 | 1996-11-14 | Substituted 16,17-secosteroids of estratrien and androsten seroes with biological activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU60496A true YU60496A (en) | 1998-12-23 |
| RS49568B RS49568B (en) | 2007-04-10 |
Family
ID=47602012
Country Status (1)
| Country | Link |
|---|---|
| RS (1) | RS49568B (en) |
-
1996
- 1996-11-14 RS YUP-604/96A patent/RS49568B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RS49568B (en) | 2007-04-10 |
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