PL239563B1 - 3β-Hydroxy-5α-chloro-17a-oxa-D-homo-6,19-oxidoandrostan-17-one and method of preparation of 3β-hydroxy-5α-chloro-17a-oxa-D-homo-6,19-oxidoandrostane-17-one - Google Patents
3β-Hydroxy-5α-chloro-17a-oxa-D-homo-6,19-oxidoandrostan-17-one and method of preparation of 3β-hydroxy-5α-chloro-17a-oxa-D-homo-6,19-oxidoandrostane-17-one Download PDFInfo
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Abstract
Przedmiotem zgłoszenia jest 3β-hydroksy-5α-chloro-17a-oksa-D-homo-6,19-oksidoandrostan-17-onn i sposób wytwarzania 3β-hydroksy-5α-chloro-17a-oksa-D-homo-6,19-oksidoandrostan-17-onu o wzorze 2. Zgodnie z rozwiązaniem, w wyniku działania układu enzymatycznego, zawartego w komórkach szczepu Penicillium chrysogenum KCh S4, następuje hydroliza grupy acetylowej przy C-3 i utlenieniu typu Baeyera-Villigera pierścienia D. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą (chloroform).The subject of the application is 3β-hydroxy-5α-chloro-17a-oxa-D-homo-6,19-oxidoandrostan-17-onen and a method for producing 3β-hydroxy-5α-chloro-17a-oxa-D-homo-6,19 -oxidoandrostan-17-one of formula 2. According to the solution, as a result of the action of the enzymatic system contained in the cells of the Penicillium chrysogenum KCh S4 strain, the acetyl group at C-3 and the Baeyer-Villiger type oxidation of the D ring are hydrolyzed. Obtained in this way the product is isolated from the aqueous culture of the microorganism in a known method, by extraction with an organic solvent immiscible with water (chloroform).
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest 3e-hydroksy-5a-chloro-17a-oksa-D-homo-6,19-oksidoandrostan-17-on i sposób wytwarzania 3e-hydroksy-5a- chloro-17a-oksa-D-homo-6,19-oksidoandrostan-17-onu.The present invention relates to 3e-hydroxy-5a-chloro-17a-oxa-D-homo-6,19-oxidoandrostane-17-one and a method for the preparation of 3e-hydroxy-5a-chloro-17a-oxa-D-homo-6.19 -oksidoandrostan-17-one.
Wynalazek może znaleźć zastosowanie w przemyśle farmaceutycznym jako prekursor leków antykoncepcyjnych.The invention may find application in the pharmaceutical industry as a precursor to contraceptive drugs.
Wprowadzenie mostka 6,19-oksiranowego w strukturze związków steroidowych powoduje ugięcie szkieletu pomiędzy pierścieniami A i B. (G. Burton, M. Galigniana, S. de Lavallaz, A. L. Brachet-Cota, E. M. Sproviero, A. A. Ghini, C. P. Lantos and M. C. Damasco, Mol. Pharmacol., 1995, 47, 535-543). Wykazano, że niektóre związki posiadające takie ugrupowanie mają interesujące aktywności biologiczne. Analog 21-hydroksyprogesteronu jest selektywnym antyglukokortykoidem pozbawionym mineralokortykoidowych i progestagenowych aktywności (G. P. Vicent, M. C. Monteserin, A. S. Veleiro, G. Burton, C. P. Lantos and M. D. Galigniana, Mol. Pharmacol., 1997, 52, 749-753), a analog 2 pregnanolonu jest silnym środkiem przeciwdrgawkowym (A. S. Veleiro, R. Rosenstein, M. L. Grilli, C. Jaliffa, F. Speroni and G. Burton, Bioorg. Med. Chem. Lett., 2003, 13, 343-346; M. Joselevich, A.A. Ghini, G. Burton 6,19-Carbon-bridged steroids. Synthesis of 6,19-methanoprogesterone. Org. Biomol. Chem. 2003, 1, 939-943). Istnieją również doniesienia dotyczące działania zapobiegającego migotaniu komór serca C-19 steroidów posiadających mostek 6,19-oksiranowy. Z opisu patentowego US 3,001,989 znane są właściwości przeciwbólowe i są bakteriostatyczne wobec bakterii Gram-dodatnich. Związki steroidowe posiadające mostek 6,19-oksiranowy są prekursorami posiadających właściwości antykoncepcyjne 19-norsteroidów (B. Berkoz, E. Denot, A. Bowers. Steroids CCXXX. Conversion of 6β, 19-oxides and lactones into 19-nor steroids. Steroids. 1, 1963, 251-270).The introduction of a 6,19-oxirane bridge in the structure of steroid compounds causes a deflection of the skeleton between the A and B rings (G. Burton, M. Galigniana, S. de Lavallaz, AL Brachet-Cota, EM Sproviero, AA Ghini, CP Lantos and MC Damasco , Mol. Pharmacol., 1995, 47, 535-543). Some compounds having such a moiety have been shown to have interesting biological activities. The 21-hydroxyprogesterone analog is a selective antiglucocorticoid devoid of mineralocorticoid and progestagenic activities (GP Vicent, MC Monteserin, AS Veleiro, G. Burton, CP Lantos and MD Galigniana, Mol. Pharmacol., 1997, 52, 749-753), and pregnanolone analog 2 is a potent anticonvulsant (AS Veleiro, R. Rosenstein, ML Grilli, C. Jaliffa, F. Speroni and G. Burton, Bioorg. Med. Chem. Lett., 2003, 13, 343-346; M. Joselevich, AA Ghini , G. Burton 6,19-Carbon-bridged steroids. Synthesis of 6,19-methanoprogesterone. Org. Biomol. Chem. 2003, 1, 939-943). There are also reports of C-19 steroids with a 6,19-oxirane bridge in preventing fibrillation. From US 3,001,989, analgesic properties are known and are bacteriostatic against gram-positive bacteria. Steroid compounds having a 6,19-oxirane bridge are the precursors of the contraceptive properties of 19-norsteroids (B. Berkoz, E. Denot, A. Bowers. Steroids CCXXX. Conversion of 6β, 19-oxides and lactones into 19-nor steroids. Steroids. 1, 1963, 251-270).
Szczep Penicillium chrysogenum KCh S4 znany jest z opisu zgłoszenia wynalazku P.420187 ujawniony jest również w publikacji (Kozłowska E., Urbaniak M., Kancelista A., Dymarska M., Kostrzewa-Susłow E.; Stępień Ł., Janeczko T., (2017) Biotransformation of dehydroepiandrosterone (DHEA) by environmental strains of filamentous fungi. RSC Advances 2017, 7, 31493-31501).The Penicillium chrysogenum KCh S4 strain is known from the description of the invention application P.420187 is also disclosed in the publication (Kozłowska E., Urbaniak M., Kancelista A., Dymarska M., Kostrzewa-Susłow E .; Stępień Ł., Janeczko T., (2017) Biotransformation of dehydroepiandrosterone (DHEA) by environmental strains of filamentous fungi. RSC Advances 2017, 7, 31493-31501).
W literaturze nie ma doniesień dotyczących 3e-hydroksy-5a-chloro-17a-oksa-D-homo-6,19-oksidoandrostan-17-onu.There are no reports in the literature on 3e-hydroxy-5a-chloro-17a-oxa-D-homo-6,19-oxidoandrostane-17-one.
Istota wynalazku polega na tym, że do podłoża odpowiedniego dla grzybów strzępkowych wprowadza się szczep Penicillium chrysogenum KCh S4. Po upływie co najmniej 48 godzin do hodowli wprowadza się substrat, którym jest 3e-acetyloksy-5a-chloro-6,19-oksidoandrostan-17-on o wzorze 1, rozpuszczony w rozpuszczalniku organicznym mieszającym się z wodą. Transformację prowadzi się w temperaturze od 20 do 30 stopni Celsjusza, przy ciągłym wstrząsaniu, co najmniej 3 dni. Kolejno produkt ekstrahuje się rozpuszczalnikiem organicznym niemieszającym się z wodą i oczyszcza chromatograficznie.The essence of the invention consists in introducing the Penicillium chrysogenum KCh S4 strain into a medium suitable for filamentous fungi. After at least 48 hours, the substrate is introduced into the culture, which is 3e-acetyloxy-5a-chloro-6,19-oxidoandrostane-17-one of the formula I, dissolved in a water-miscible organic solvent. The transformation is carried out at a temperature of 20 to 30 degrees Celsius with continuous shaking for at least 3 days. Subsequently, the product is extracted with a water-immiscible organic solvent and purified by chromatography.
W wyniku hydrolizy grupy acetylowej przy C-3 i utlenieniu typu Baeyera-Villigera pierścienia D, otrzymuje się 3e-hydroksy-5a-chloro-17a-oksa-D-homo-6,19-oksidoandrostan-17-on, a reakcję prowadzi się w wodnej kulturze szczepu Penicillium chrysogenum KCh S4.As a result of the hydrolysis of the acetyl group at C-3 and the Baeyer-Villiger type oxidation of the D ring, 3e-hydroxy-5a-chloro-17a-oxa-D-homo-6,19-oxidoandrostane-17-one is obtained, and the reaction is carried out in the water culture of the strain Penicillium chrysogenum KCh S4.
Korzystnie jest, gdy stosunek masy dodawanego substratu do objętości hodowli wynosi 0,2 g : 1 L.Preferably, the ratio of the weight of the added substrate to the culture volume is 0.2 g: 1 L.
Korzystnie także jest, gdy proces prowadzi się w temperaturze 25 stopni Celsjusza.It is also preferred that the process is carried out at a temperature of 25 degrees Celsius.
Dodatkowo, korzystnie jest, gdy transformację prowadzi się przez 3 dni.Additionally, it is preferred that the transformation is carried out for 3 days.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w komórkach szczepu Penicillium chrysogenum KCh S4, następuje hydroliza grupy acetylowej przy C-3 i utlenienie pierścienia D typu Baeyer-Villigera. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem, przez ekstrakcję rozpuszczalnikiem organicznym niemieszającym się z wodą (chloroform).In accordance with the invention, hydrolysis of the acetyl group at C-3 and oxidation of the D-ring of the Baeyer-Villiger type occurs as a result of the enzyme system contained in the cells of the Penicillium chrysogenum KCh S4 strain. The product obtained in this way is separated from the aqueous culture of the microorganism by a known method by extraction with a water-immiscible organic solvent (chloroform).
Zasadniczą zaletą wynalazku jest otrzymanie 3e-hydroksy-5a-chioro-17a-oksa-D-homo-6,19-oksidoandrostan-17-onu, z wydajnością izolowaną na poziomie 50% (konwersja według GC = 99%), w temperaturze pokojowej i przy pH naturalnym dla szczepu.The main advantage of the invention is the preparation of 3e-hydroxy-5a-chioro-17a-oxa-D-homo-6,19-oxidoandrostane-17-one with an isolated efficiency of 50% (conversion according to GC = 99%), at room temperature and at the natural pH of the strain.
Wynalazek jest bliżej objaśniony na przykładzie wykonania.The invention is explained in more detail using an exemplary embodiment.
P r z y k ł a dExample
Do kolby Erlenmajera o pojemności 2000 cm3, w której znajduje się 500 cm3 sterylnej pożywki zawierającej 5 g aminobaku i 15 g glukozy, wprowadza się szczep Penicillium chrysogenum KCh S4. Po 72 godzinach jego wzrostu dodaje się 100 mg 3e-acetyloksy-5a-chloro-6,19-oksidoandrostan-17-onu o wzorze 1, rozpuszczonego w 1 cm3 DMSO. Transformację prowadzi się w 25 stopniach CelsjuszaTo the Erlenmeyer flask with a capacity of 2,000 cm 3, which is 500 cm 3 of a sterile medium containing 5 g aminobaku and 15 g of glucose, is introduced into the strain of Penicillium chrysogenum SDS S4. After 72 hours of its growth, 100 mg of 3e-acetyloxy-5a-chloro-6,19-oxidoandrostane-17-one of formula 1, dissolved in 1 cm 3 of DMSO, are added. The transformation is carried out at 25 degrees Celsius
PL 239 563 B1 przy ciągłym wstrząsaniu przez 3 dni. Następnie mieszaninę poreakcyjną ekstrahuje się trzykrotnie chloroformem, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymany ekstrakt oczyszcza się chromatograficznie, używając jako eluentu mieszaniny heksan i aceton 2:1.With continuous shaking for 3 days. The reaction mixture was then extracted three times with chloroform, dried with anhydrous magnesium sulfate, and the solvent was evaporated. The extract obtained is purified by chromatography using a 2: 1 mixture of hexane and acetone as the eluent.
Na tej drodze otrzymuje się 50 mg 3β-hydroksy-5α-chloro-17a-oksa-D-homo-6,19-oksidoandrostan-17-onu (konwersja według GC = 99%).In this way, 50 mg of 3β-hydroxy-5α-chloro-17a-oxa-D-homo-6,19-oxidoandrostane-17-one are obtained (GC conversion = 99%).
Uzyskany produkt charakteryzuje się następującymi danymi; spektralnymi:The obtained product is characterized by the following data; spectral:
1H NMR (600 MHz) (ppm) (CDCI3) δ: 1.06 (qd, 1H, J = 13.0, 3.5 Hz, 11-Κβ); 1.34 (s, 3H, 18-H); 1.43 (qd, 1H, J = 11.3, 5.8 Hz, 8-H); 1.45-1.49 (m, 2H, 1-Ha, 7-Ha); 1.54 (tt, 1H, J = 13.2, 8.6 Hz, 15-Hβ); 1.60-1.68 (m, 1H, 1-Κβ, 11-Ha, 14-H); 1.72 (dd, 1H, J = 12.6; 3.5 Hz, 12-Ha); 1.75 (ddd, 1H, J = 13.3, 5.6, 5.1 Hz, 2-Ha); 1.82-1.92 (m, 3H, 2-Hβ, 9-H, 15-Ha); 1.96 (ddd, 1H, J = 10.0, 5.0, 2.4 Hz, 7Ήβ); 2.01 (dt, 1H, J = 12.3, 3.2 Hz, 12-Κβ); 2.03 (dd, 1H, J = 13.6, 11.3 Hz, 4-Ha); 2.21 (ddd, 1H, J = 13.7, 4.3, 2.3 Hz, 4-Hβ); 2.57 (ddd, 1H, J = 19.0, 9.1, 8.4 Hz, 16-Ha); 2.68 (ddd, 1H, J = 19.0, 8.6, 2.4 Hz, 16-Hβ); 3.72 (d, 1H, J = 8.7 Hz, one of 19-H); 3.92 (dd, 1H. J = 8.7, 0.9 Hz, one of 19-H); 4.04 (d, 1H, J = 4.8 Hz, 6-Ha); 4.07 (tt, 1H, J = 11.1, 4.6 Hz, 3-Ha). 13C NMR (151 MHz) (ppm) (CDCI3) δ: 23,40 (C-1); 30,97 (C-2); 66,34 (C-3); 43,72 (C-4); 75,61 (C-5); 81,76 (C- 6); 30,70 (C-7); 35,73 (C-8); 45,64 (C-9); 45,71 (C-10); 23,34 (C-11); 39,32 (C-12); 83,08 (C-13); 44,84 (C-14); 19,55 (C-15); 28,63 (C-16); 171,39 (C-17); 20,47 (C-18); 68,30 (C-19). 1 H NMR (600 MHz) (ppm) (CDCl 3) δ: 1.06 (qd, 1H, J = 13.0, 3.5 Hz, 11-Κβ); 1.34 (s, 3H, 18-H); 1.43 (qd, 1H, J = 11.3, 5.8 Hz, 8-H); 1.45-1.49 (m, 2H, 1-Ha, 7-Ha); 1.54 (mp, 1H, J = 13.2, 8.6 Hz, 15-Hβ); 1.60-1.68 (m, 1H, 1-Κβ, 11-Ha, 14-H); 1.72 (dd, 1H, J = 12.6, 3.5 Hz, 12-Ha); 1.75 (ddd, 1H, J = 13.3, 5.6, 5.1 Hz, 2-Ha); 1.82-1.92 (m, 3H, 2-Hβ, 9-H, 15-Ha); 1.96 (ddd, 1H, J = 10.0, 5.0, 2.4 Hz, 7Ήβ); 2.01 (dt, 1H, J = 12.3, 3.2 Hz, 12-Κβ); 2.03 (dd, 1H, J = 13.6, 11.3 Hz, 4-Ha); 2.21 (ddd, 1H, J = 13.7, 4.3, 2.3 Hz, 4-Hβ); 2.57 (ddd, 1H, J = 19.0, 9.1, 8.4 Hz, 16-Ha); 2.68 (ddd, 1H, J = 19.0, 8.6, 2.4 Hz, 16-Hβ); 3.72 (d, 1H, J = 8.7Hz, one of 19-H); 3.92 (dd, 1H. J = 8.7, 0.9 Hz, one of 19-H); 4.04 (d, 1H, J = 4.8 Hz, 6-Ha); 4.07 (mp, 1H, J = 11.1, 4.6 Hz, 3-Ha). 13 C NMR (151 MHz) (ppm) (CDCl 3) δ: 23.40 (C-1); 30.97 (C-2); 66.34 (C-3); 43.72 (C-4); 75.61 (C-5); 81.76 (C- 6); 30.70 (C-7); 35.73 (C-8); 45.64 (C-9); 45.71 (C-10); 23.34 (C-11); 39.32 (C-12); 83.08 (C-13); 44.84 (C-14); 19.55 (C-15); 28.63 (C-16); 171.39 (C-17); 20.47 (C-18); 68.30 (C-19).
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