PL195740B1 - Novel leading structure of isoxazole derivative - Google Patents
Novel leading structure of isoxazole derivativeInfo
- Publication number
- PL195740B1 PL195740B1 PL343052A PL34305200A PL195740B1 PL 195740 B1 PL195740 B1 PL 195740B1 PL 343052 A PL343052 A PL 343052A PL 34305200 A PL34305200 A PL 34305200A PL 195740 B1 PL195740 B1 PL 195740B1
- Authority
- PL
- Poland
- Prior art keywords
- isoxazole
- isoxazole derivative
- leading structure
- amino
- novel leading
- Prior art date
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Nowa struktura wiodąca pochodnej izoksazolu o nazwie 5-amino-3-metylo-4-(2,5-dimetylopiroloaminokarbonylo)-izoksazol i wzorze przedstawionym na rysunku.A new leading structure of an isoxazole derivative named 5-amino-3-methyl-4-(2,5-dimethylpyrroleaminocarbonyl)-isoxazole and with the formula shown in the figure.
Description
Przedmiotem wynalazku jest nowa struktura wiodąca pochodnej izoksazolu o nazwie 5-amino-3-metylo-4-(2,5-dimetylopiroloaminokarbonylo)-izoksazol i wzorze przedstawionym na rysunku, wykazująca oddziaływanie biologiczne o aktywności immunotropowej.The subject of the invention is a new leading structure of an isoxazole derivative called 5-amino-3-methyl-4-(2,5-dimethylpyrroleaminocarbonyl)-isoxazole and with the formula shown in the drawing, demonstrating biological activity with immunotropic activity.
Wynalazek dotyczy nowej struktury wiodącej pochodnej izoksazolu o nazwie 5-amino-3-metylo-4-(2,5-dimetylopiroloaminokarbonylo)-izoksazol i wzorze przedstawionym na rysunku.The invention relates to a new structure of the leading isoxazole derivative named 5-amino-3-methyl-4-(2,5-dimethylpyrroleaminocarbonyl)-isoxazole and the formula shown in the drawing.
Nową pochodną otrzymuje się w reakcji hydrazydu kwasu 5-amino-3-metyloizoksazolo-4-karboksylowego (V) z heksadionem-2,5, w obecności izopropanolu.The new derivative is obtained by the reaction of 5-amino-3-methylisoxazole-4-carboxylic acid hydrazide (V) with hexadione-2,5 in the presence of isopropanol.
Podczas badań nieoczekiwanie okazało się, że nowy związek wykazuje aktywność immunotropową porównywalną z Cyklosporyną A (CSA). W dwu testach produkcji znaczących cytokin: TNF-a oraz Interleukiny-6 (IL-6) stwierdzono znaczące oddziaływanie biologiczne, które przedstawia poniższe zestawienie.During the study, it was unexpectedly revealed that the new compound exhibited immunotropic activity comparable to Cyclosporine A (CSA). Two assays for the production of significant cytokines: TNF-α and Interleukin-6 (IL-6) demonstrated significant biological effects, as summarized below.
Sposób otrzymywania nowego 5-amino-3-metylo-4-(2,5-dimetylopirolo-aminokarbonylo)-izoksazolu przedstawia przykład wykonania.The method for obtaining the new 5-amino-3-methyl-4-(2,5-dimethylpyrrole-aminocarbonyl)-isoxazole is presented in the following embodiment.
Porcję 3 mmoli hydrazydu kwasu 5-amino-3-metyloizoksazolo-4-karboksylo-wego umieszcza się w kolbie okrągłodennej o pojemności 100 mL, zaopatrzonej w chłodnicę zwrotną i mieszadełko, a następnie dodaje się 50 mL izopropanolu i 3,3 mmoli heksadionu-2,5. Całość miesza się na mieszadle magnetycznym i ogrzewa do temperatury wrzenia w ciągu 10 minut. Mieszaninę reakcyjną utrzymuje się we wrzeniu przez następne 7 godzin. Po zakończeniu procesu, kontrolowanym na płytkach TLC, zawiesinę ochładza się, po czym odsącza. Surowy produkt przekrystalizowuje się z etanolu, otrzymując biały, krystaliczny produkt z wydajnością 49,3% wydajności teoretycznej, o temperaturze topnienia 224-225 C.A 3 mmol portion of 5-amino-3-methylisoxazole-4-carboxylic acid hydrazide was placed in a 100 mL round-bottomed flask equipped with a reflux condenser and a stirrer bar, followed by the addition of 50 mL of isopropanol and 3.3 mmol of 2,5-hexadione. The mixture was stirred on a magnetic stirrer and heated to reflux for 10 minutes. The reaction mixture was heated at reflux for another 7 hours. After completion of the reaction, as monitored by TLC plates, the suspension was cooled and filtered. The crude product was recrystallized from ethanol to give a white crystalline product in 49.3% of theory, melting at 224-225°C.
Analizę nowej pochodnej przeprowadzono następująco.The analysis of the new derivative was performed as follows.
Temperatury topnienia oznaczono na aparacie Boethiusa i nie korygowano.Melting points were determined on the Boethius apparatus and are uncorrected.
Widma IR mierzono w KBr na aparacie Specord M-80.IR spectra were measured in KBr on a Specord M-80 instrument.
Widma 1H NMR oznaczono na aparacie Tesla 80 MHz. Przesunięcia chemiczne oznaczono wobec tetrametylosilanu (TMS) jako zewnętrznego standardu.1H NMR spectra were determined on an 80 MHz Tesla instrument. Chemical shifts were determined against tetramethylsilane (TMS) as an external standard.
Widma MS mierzono na spektrometrze LKB 9000.MS spectra were measured on an LKB 9000 spectrometer.
Wszystkie związki analizowano na zawartość (%) C, H, N. Różnice pomiędzy wartościami, obliczoną i znalezioną, nie przekraczały ± 0,3%.All compounds were analyzed for the content (%) of C, H, N. The differences between the calculated and found values did not exceed ± 0.3%.
Wartości wyznaczone są następujące:The values determined are as follows:
IR (KBr)vc=ocm-1 1712 c=oIR (KBr)vc=ocm -1 1712 c=o
1H NMR(DMSO-d6)/TMS d, J (Hz): 2,1 (s, 6H, 2CH-pirol); 2,4 (s, 3H, CH3-izoksazol); 5 7 (s, 2H, -NH2); 7,6 (s, 2H, 2CH-pirol); 9,7 (s, 1H, NH)1H NMR(DMSO-d6)/TMS d, J (Hz): 2.1 (s, 6H, 2CH-pyrrole); 2.4 (s, 3H, CH3-isoxazole); 5 7 (s, 2H, -NH2); 7.6 (s, 2H, 2CH-pyrrole); 9.7 (s, 1H, NH)
MS(70 eV),m/z(%) 233,0.MS(70 eV),m/z(%) 233.0.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL343052A PL195740B1 (en) | 2000-10-06 | 2000-10-06 | Novel leading structure of isoxazole derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL343052A PL195740B1 (en) | 2000-10-06 | 2000-10-06 | Novel leading structure of isoxazole derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL343052A1 PL343052A1 (en) | 2002-04-08 |
| PL195740B1 true PL195740B1 (en) | 2007-10-31 |
Family
ID=20077530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL343052A PL195740B1 (en) | 2000-10-06 | 2000-10-06 | Novel leading structure of isoxazole derivative |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL195740B1 (en) |
-
2000
- 2000-10-06 PL PL343052A patent/PL195740B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL343052A1 (en) | 2002-04-08 |
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