PL144840B1 - Method of obtaining 5- and 6-alkyl-1,5- and 1,6-benzo/h/naphthyridinium iodides - Google Patents
Method of obtaining 5- and 6-alkyl-1,5- and 1,6-benzo/h/naphthyridinium iodides Download PDFInfo
- Publication number
- PL144840B1 PL144840B1 PL25527785A PL25527785A PL144840B1 PL 144840 B1 PL144840 B1 PL 144840B1 PL 25527785 A PL25527785 A PL 25527785A PL 25527785 A PL25527785 A PL 25527785A PL 144840 B1 PL144840 B1 PL 144840B1
- Authority
- PL
- Poland
- Prior art keywords
- benzo
- iodides
- naphthyridinium
- allyl
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000004694 iodide salts Chemical class 0.000 title claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 5
- HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania nowych zwiazków chemicznych, wykazujacych dzialanie przeciwbakteryjne.Zgodnie z wynalazkiem jodki 5- i 6-allilo-1,5- i 1,6-benzo[h] -naftyrydyniowe wytwarza sie metoda czwartorzedowania 1,5- i 1,6-benzo[h]naftyrydyny. Roztwór 1,5- lub 1,6-benzoJh]naf- tyrydyny w tetrahydrofuranie traktuje sie jodkiem allilu, mieszajac calosc w warunkach bezwod¬ nych w temperaturze pokojowej* Wydzielona" substancje stala oczyszcza sie poprzez krystalizacje* Jodki wytworzone sposobem wedlug wynalazku wykazuja czynnosc inhibitowania wzrostu bakte¬ rii. Ze wzgledu na swe wlasnosci biologiczne moga byc wykorzystane jako srodki przeciwbakteryj¬ ne. Przedmiot wynalazku jest blizej omówiony w przykladach wytwarzania jodków.Przyklad I. 1,8 g (10 mraol) 1,5-benzo[h] naftyrydyny rozpuszcza sie w 10 ml tetra- hydrofuranu, po czym otrzymany roztwór poddaje sie reakcji z 2,52 g (15 mmol) jodku allilu i miesza mechanicznie przez okres 12 godzin w warunkach bezwodnych w temperaturze pokojowej. Wy¬ dzielony produkt krystalizuje sie z mieszaniny metanol/tetrahydrofuran 1:1.Wytworzony jodek 5-allilo-1,5-benzo[h]naftyrydyniowy (wzór 1) wykazuje temperature top¬ nienia 211-212°C. Wydajnosc procesu wynosi 31## Badania wykazaly wyrazne dzialanie przeciwbak- teryjne otrzymanego zwiazku. Jego minimalne stezenie inhibitujace wzrost bakterii wynosi 2,50 mg/ml w przypadku bakterii Escherichia coli 0111 oraz 0,60 mg/ml w przypadku bakterii Staphy- lococcus aureus 209 P.Przyklad II# 1,8 g (10 mraol) 1 , 6-tenzo/hJnaftyrydyny rozpuszcza sie w 10 ml te- trahydrofuranu, po czym otrzymany roztwór poddaje sie reakcji z 2,52 g (15 mmol) jodku allilu i miesza mechanicznie przez okres 12 godzin w warunkach bezwodnych w temperaturze pokojowej.Wydzielony produkt krystalizuje sie z mieszaniny metanol/tetrahydrofuran 1:1. Wytworzony jo¬ dek 6~allilo-1,6-berizo[h]naftyrydyniowy (wzór 2) wykazuje temperature topnienia 204-205°C.Wydajnosc procesu wynosi 35,6#. Minimalne stezenie otrzymanego zwiazku, inhibitu^ce wzrost2 144 840 bakterii Escherichia coli 0111 wynosi 0,93 mg/ml. Minimalne stezenie zwiazku, inhibitujace wzrost bakterii Staphylococcus aureus 209 P wynosi 0,95 mg/ml.Zastrzezenie patentowe Sposób wytwarzania nowych jodków 5- i 6-alllilo-1f5- i 1,6-benzoJhJnaftyrydyniowych, znamienny tym, ze roztwór 1,5- lub 1,6-benzo[hJ naftyrydyny w tetrahydrofuranie traktuje sie jodkiem allilu, mieszajac calosc w warunkach bezwodnych w temperaturze pokojowej, po czym wydzielona substancje stala oczyszcza sie poprzez krystalizacje.CH2-CH«CH2 WZÓR 1 r0 CH2-CH=CH2 WZÓR Z Pracownia Poligraficzna UP PRL. Naklad 100 egz.Cena 220 zl PLThe subject of the invention is a method for the preparation of new chemical compounds showing antibacterial activity. According to the invention, 5- and 6-allyl-1,5- and 1,6-benzo [h] -naphthyridinium iodides are prepared by the 1,5- and 1 quaternization method. 6-benzo [h] naphthyridine. A solution of 1,5- or 1,6-benzoJh] naphthyridine in tetrahydrofuran is treated with allyl iodide, while stirring it under anhydrous conditions at room temperature * The separated "solids are purified by crystallization * The iodides prepared according to the invention show an inhibitory activity. Due to their biological properties, they can be used as antibacterial agents. The subject of the invention is discussed in more detail in the examples of iodide production. Example I. 1.8 g (10 mraoles) of 1,5-benzo [h] naphthyridine is dissolved in 10 ml of tetrahydrofuran, then the obtained solution is reacted with 2.52 g (15 mmol) of allyl iodide and mechanically stirred for 12 hours under anhydrous conditions at room temperature. The separated product is crystallized from the mixture with methanol. / tetrahydrofuran 1: 1. The produced 5-allyl-1,5-benzo [h] naphthyridinium iodide (formula 1) has a melting point of 211-212 ° C. The process yield is 31 ## The research has shown a clear effect antibacterial coating of the compound obtained. Its minimum concentration inhibiting bacterial growth is 2.50 mg / ml for Escherichia coli 0111 and 0.60 mg / ml for Staphylococcus aureus 209 P. Example II # 1.8 g (10 mraol) 1, 6 -tenzo / hJ-naphthyridine is dissolved in 10 ml of tetrahydrofuran, then the obtained solution is reacted with 2.52 g (15 mmol) of allyl iodide and mechanically stirred for 12 hours under anhydrous conditions at room temperature. The separated product crystallizes from 1: 1 methanol / tetrahydrofuran mixtures. The 6-allyl-1,6-berizo [h] naphthyridinium ionecane produced (Formula 2) has a melting point of 204-205 ° C. The yield of the process is 35.6%. The minimum concentration of the obtained compound that inhibits the growth of Escherichia coli 0111 bacteria is 0.93 mg / ml. The minimum concentration of the compound, which inhibits the growth of Staphylococcus aureus 209 P bacteria, is 0.95 mg / ml. or 1,6-benzo [hJ naphthyridine in tetrahydrofuran is treated with allyl iodide, with stirring under anhydrous conditions at room temperature, then the separated solid is purified by crystallization. Printing workshop of the UP PRL. Mintage 100 copies Price PLN 220 PL
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL25527785A PL144840B1 (en) | 1985-09-04 | 1985-09-04 | Method of obtaining 5- and 6-alkyl-1,5- and 1,6-benzo/h/naphthyridinium iodides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL25527785A PL144840B1 (en) | 1985-09-04 | 1985-09-04 | Method of obtaining 5- and 6-alkyl-1,5- and 1,6-benzo/h/naphthyridinium iodides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL255277A1 PL255277A1 (en) | 1986-06-03 |
| PL144840B1 true PL144840B1 (en) | 1988-07-30 |
Family
ID=20028210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL25527785A PL144840B1 (en) | 1985-09-04 | 1985-09-04 | Method of obtaining 5- and 6-alkyl-1,5- and 1,6-benzo/h/naphthyridinium iodides |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL144840B1 (en) |
-
1985
- 1985-09-04 PL PL25527785A patent/PL144840B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL255277A1 (en) | 1986-06-03 |
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