PL408241A1 - New derivatives of 9,10-anthraquinone containing the piperazine systems and method for obtaining new derivatives of 9,10-anthraquinone containing the piperazine systems - Google Patents
New derivatives of 9,10-anthraquinone containing the piperazine systems and method for obtaining new derivatives of 9,10-anthraquinone containing the piperazine systemsInfo
- Publication number
- PL408241A1 PL408241A1 PL408241A PL40824114A PL408241A1 PL 408241 A1 PL408241 A1 PL 408241A1 PL 408241 A PL408241 A PL 408241A PL 40824114 A PL40824114 A PL 40824114A PL 408241 A1 PL408241 A1 PL 408241A1
- Authority
- PL
- Poland
- Prior art keywords
- anthraquinone
- piperazine
- obtaining
- systems
- new derivatives
- Prior art date
Links
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 5
- 150000004058 9,10-anthraquinones Chemical class 0.000 title abstract 4
- 229940076442 9,10-anthraquinone Drugs 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 abstract 3
- 150000003053 piperidines Chemical class 0.000 abstract 3
- KKECLMYNUGARQZ-UHFFFAOYSA-N 1-piperidin-1-ylanthracene-9,10-dione Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1N1CCCCC1 KKECLMYNUGARQZ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 abstract 2
- DAIHUPKTACJBDY-UHFFFAOYSA-N (9,10-dioxoanthracen-1-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O DAIHUPKTACJBDY-UHFFFAOYSA-N 0.000 abstract 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 abstract 1
- QFDHYBLCHGMWDI-UHFFFAOYSA-N 1-fluoroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2F QFDHYBLCHGMWDI-UHFFFAOYSA-N 0.000 abstract 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 230000032823 cell division Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000824 cytostatic agent Substances 0.000 abstract 1
- 230000001085 cytostatic effect Effects 0.000 abstract 1
- 239000003480 eluent Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 abstract 1
- 235000019341 magnesium sulphate Nutrition 0.000 abstract 1
- 239000012044 organic layer Substances 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000000741 silica gel Substances 0.000 abstract 1
- 229910002027 silica gel Inorganic materials 0.000 abstract 1
- 239000000758 substrate Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Przedmiotem wynalazku są pochodne 9,10-antrachinonu zawierające układy piperazynowe i sposób otrzymywania pochodnych 9,10-antrachinonu zawierających układy piperazynowe. Wynalazek dotyczy grupy nowych antybiotyków cytostatycznych hamujących podział komórek. Piperydynowa pochodna 9,10-antrachinonu charakteryzuje się tym, że stanowi ją 1-(piperydyn-1-ylo)-9,10-antrachinon zawierający w swojej strukturze pierścień piperazyny w położeniu 1 pierścienia 9,10-antrachinonowego gdzie R1 = H, R2 = H, R3 = H o wzorze 1. Ujawniono także sposób otrzymywania piperydynowej pochodnej 9,10-antrachinonu, stanowiącej 1-(piperydyn-1-ylo)-9,10-antrachinon zawierający w swojej strukturze pierścień piperadyny. Sposób polega na tym, że wykorzystuje się jako substrat wyjściowy 1-chloro-9,10-antrachinon, lub 1-fluoro-9,10-antrachinon, lub 1-tosyloxy-9,10-antrachinon, na którym przeprowadza się reakcję w środowisku toluenu, lub w środowisku izopropanolu lub w środowisku etanolu, ogrzewając mieszaninę reakcyjną do temperatury 80°C przez czas około 24 godziny, po upływie którego otrzymane po reakcji związki przemywa się wodą technologiczną chemicznie i bakteriologicznie unieczynnioną. Otrzymaną warstwę organiczną suszy się w bezwodnym MgSO4, po czym tak otrzymany surowy półprodukt izoluje się na żelu krzemionkowym stosując jako eluent układ chlorek metylenu i metanol w stosunku (5:0,1), uzyskując w wyniku piperydynową pochodną 9,10-antrachinonu z wydajnością około 90%.The subject of the invention are 9,10-anthraquinone derivatives containing piperazine systems and a method for obtaining 9,10-anthraquinone derivatives containing piperazine systems. The invention concerns a group of new cytostatic antibiotics that inhibit cell division. The piperidine derivative of 9,10-anthraquinone is characterized by the fact that it is 1-(piperidin-1-yl)-9,10-anthraquinone containing in its structure a piperazine ring in position 1 of the 9,10-anthraquinone ring where R1 = H, R2 = H, R3 = H of formula 1. Also disclosed is a method for obtaining a piperidine derivative of 9,10-anthraquinone, which is 1-(piperidin-1-yl)-9,10-anthraquinone containing a piperadine ring in its structure. The method involves using 1-chloro-9,10-anthraquinone, or 1-fluoro-9,10-anthraquinone, or 1-tosyloxy-9,10-anthraquinone as a starting substrate, on which the reaction is carried out in the medium toluene, or in isopropanol or ethanol, by heating the reaction mixture to 80°C for about 24 hours, after which the compounds obtained after the reaction are washed with chemically and bacteriologically inactivated process water. The obtained organic layer is dried in anhydrous MgSO4, and then the crude intermediate thus obtained is isolated on silica gel using methylene chloride and methanol in a ratio (5:0.1) as an eluent, obtaining the piperidine derivative of 9,10-anthraquinone with the yield about 90%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL408241A PL232524B1 (en) | 2014-05-19 | 2014-05-19 | New derivatives of 9,10-anthraquinone containing the piperazine systems and method for obtaining new derivatives of 9,10-anthraquinone containing the piperazine systems |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL408241A PL232524B1 (en) | 2014-05-19 | 2014-05-19 | New derivatives of 9,10-anthraquinone containing the piperazine systems and method for obtaining new derivatives of 9,10-anthraquinone containing the piperazine systems |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL408241A1 true PL408241A1 (en) | 2015-11-23 |
| PL232524B1 PL232524B1 (en) | 2019-06-28 |
Family
ID=54543826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL408241A PL232524B1 (en) | 2014-05-19 | 2014-05-19 | New derivatives of 9,10-anthraquinone containing the piperazine systems and method for obtaining new derivatives of 9,10-anthraquinone containing the piperazine systems |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL232524B1 (en) |
-
2014
- 2014-05-19 PL PL408241A patent/PL232524B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL232524B1 (en) | 2019-06-28 |
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