PL419151A1 - Betulinic acid ester and method for obtaining it - Google Patents
Betulinic acid ester and method for obtaining itInfo
- Publication number
- PL419151A1 PL419151A1 PL419151A PL41915116A PL419151A1 PL 419151 A1 PL419151 A1 PL 419151A1 PL 419151 A PL419151 A PL 419151A PL 41915116 A PL41915116 A PL 41915116A PL 419151 A1 PL419151 A1 PL 419151A1
- Authority
- PL
- Poland
- Prior art keywords
- betulinic acid
- acid ester
- obtaining
- farnesol
- ester
- Prior art date
Links
- QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 title abstract 4
- CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 title abstract 4
- DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 title abstract 4
- PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 title abstract 4
- MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 title abstract 4
- -1 Betulinic acid ester Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 abstract 2
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 abstract 2
- 229940043259 farnesol Drugs 0.000 abstract 2
- 229930002886 farnesol Natural products 0.000 abstract 2
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest ester kwasu betulinowego o wzorze 1 przedstawionym na rysunku oraz sposób jego otrzymywania. Sposób polega na tym, że kwas betulinowy przeprowadzony w pochodną octanową poddaje się estryfikacji w obecności odczynnika chlorującego i przy czym dodaje się dwukrotny nadmiar molowy farnezolu, a następnie usuwa się grupę zabezpieczającą w pozycji C-3 w drodze selektywnej hydrolizy. Ester kwasu betulinowego z farnezolem stanowi nośnik aktywnych biologicznie molekuł o działaniu przeciwnowotworowym. Ester może znaleźć zastosowanie w przemyśle farmaceutycznym, np. w terapii chorób nowotworowych.The subject of the application is the betulinic acid ester of formula 1 shown in the drawing and the method of its preparation. The method consists in the fact that betulinic acid converted into an acetate derivative is subjected to esterification in the presence of a chlorinating reagent and a two-fold molar excess of farnesol is added, followed by removal of the protecting group at the C-3 position by selective hydrolysis. Betulinic acid ester with farnesol is a carrier of biologically active molecules with anticancer activity. The ester can find application in the pharmaceutical industry, e.g. in the treatment of cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL419151A PL419151A1 (en) | 2016-10-18 | 2016-10-18 | Betulinic acid ester and method for obtaining it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL419151A PL419151A1 (en) | 2016-10-18 | 2016-10-18 | Betulinic acid ester and method for obtaining it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL419151A1 true PL419151A1 (en) | 2017-06-05 |
Family
ID=58793890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL419151A PL419151A1 (en) | 2016-10-18 | 2016-10-18 | Betulinic acid ester and method for obtaining it |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL419151A1 (en) |
-
2016
- 2016-10-18 PL PL419151A patent/PL419151A1/en unknown
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