PL219472B1 - Method for producing methanol tri hydrate complex di[bis((S)-2-amino-3-(4-hydroxyphenyl)propane)(2,2 '-dipyridyl)nickel(II)] - Google Patents
Method for producing methanol tri hydrate complex di[bis((S)-2-amino-3-(4-hydroxyphenyl)propane)(2,2 '-dipyridyl)nickel(II)]Info
- Publication number
- PL219472B1 PL219472B1 PL401095A PL40109512A PL219472B1 PL 219472 B1 PL219472 B1 PL 219472B1 PL 401095 A PL401095 A PL 401095A PL 40109512 A PL40109512 A PL 40109512A PL 219472 B1 PL219472 B1 PL 219472B1
- Authority
- PL
- Poland
- Prior art keywords
- nickel
- dipyridyl
- hydroxyphenyl
- amino
- bis
- Prior art date
Links
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 title claims description 20
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 title claims description 10
- JFFGZZIDRGUJFI-UHFFFAOYSA-N methanol trihydrate Chemical compound O.O.O.OC JFFGZZIDRGUJFI-UHFFFAOYSA-N 0.000 title claims description 5
- GIKNHHRFLCDOEU-ZETCQYMHSA-N 4-[(2s)-2-aminopropyl]phenol Chemical compound C[C@H](N)CC1=CC=C(O)C=C1 GIKNHHRFLCDOEU-ZETCQYMHSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 26
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 8
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 150000004684 trihydrates Chemical class 0.000 claims description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 241000589540 Pseudomonas fluorescens Species 0.000 description 2
- 241000607715 Serratia marcescens Species 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- LLWMGDGDBQDPSI-OWJCAWTQSA-L disodium;(2s)-2-amino-3-(4-hydroxyphenyl)propanoate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CC1=CC=C(O)C=C1.[O-]C(=O)[C@@H](N)CC1=CC=C(O)C=C1 LLWMGDGDBQDPSI-OWJCAWTQSA-L 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest sposób wytwarzania kompleksu tri hydrat metanol di[bis((S)-2-amino-3-(4-hydroksyfenylo)propano)(2,2'-dipirydyl)nikiel(II)] znajdujący zastosowanie jako składnik maści oraz środków dezynfekujących.The subject of the invention is a process for the preparation of the trihydrate complex methanol di [bis ((S) -2-amino-3- (4-hydroxyphenyl) propano) (2,2'-dipyridyl) nickel (II)] used as a component of ointments and agents disinfectants.
Dotychczas nie jest znany w literaturze sposób wytwarzania kompleksu tri hydrat metanol di[bis((S)-2-amino-3-(4-hydroksyfenylo)propano)(2,2'-dipirydyl)nikiel(II)].So far, there is no known method in the literature for the preparation of the complex methanol trihydrate di [bis ((S) -2-amino-3- (4-hydroxyphenyl) propano) (2,2'-dipyridyl) nickel (II)].
Istota sposobu wytwarzania kompleksu tri hydrat metanol di[bis((S)-2-amino-3-(4-hydroksyfenylo)propano)(2,2'-dipirydyl)nikiel(II)], o wzorze 1, polega na tym że sześciowodny chlorek niklu(II) o wzorze 2 rozpuszcza się w wodzie, a następnie 2,2'-dipirydyl o wzorze 3 rozpuszcza się w alkoholu metylowym, który dodaje się kroplami przy ciągłym mieszaniu do roztworu chlorku niklu(II), po czym do tak utworzonej mieszaniny dodaje się rozpuszczoną w wodzie uwodnioną sól disodową kwasu (S)-2-amino-3-(4-hydroksyfenylo)propanowego (L-Tyr) o wzorze 4 i po minimum 24 godzinach wydziela się w postaci krystalicznej kompleks tri hydrat metanol di[bis((S)-2-amino-3-(4-hydroksyfenylo)propano)(2,2'-dipirydyl)nikiel(II)] o wzorze 1.The essence of the process for the preparation of the methanol di [bis ((S) -2-amino-3- (4-hydroxyphenyl) propano) (2,2'-dipyridyl) nickel (II)] trihydrate complex of formula 1 is that nickel (II) chloride hexahydrate of formula 2 is dissolved in water, and then 2,2'-dipyridyl of formula 3 is dissolved in methyl alcohol which is added dropwise with continuous stirring to the nickel (II) chloride solution and then to the same of the mixture formed, the hydrated disodium salt of (S) -2-amino-3- (4-hydroxyphenyl) propanoic acid (L-Tyr) of the formula 4 is added dissolved in water, and the trihydrate complex methanol di is separated in a crystalline form after minimum 24 hours. [bis ((S) -2-amino-3- (4-hydroxyphenyl) propano) (2,2'-dipyridyl) nickel (II)] of formula 1.
Sposób według wynalazku jest przedstawiony w przykładzie realizacji.The method according to the invention is shown in an exemplary embodiment.
P r z y k ł a d 1P r z k ł a d 1
Sposób otrzymywania kompleksu tri hydrat metanol di[bis((S)-2-amino-3-(4-hydroksyfenylo)propano)(2,2’-dipirydyl)nikiel(II)] o wzorze ogólnym 1, [Ni(L-Tyr)2(bpy)]2 · 3H2O · CH3OH.Method for the preparation of the complex trihydrate methanol di [bis ((S) -2-amino-3- (4-hydroxyphenyl) propano) (2,2'-dipyridyl) nickel (II)] with the general formula 1, [Ni (L- Tyr) 2 (bpy)] 2 · 3H 2 O · CH 3 OH.
Stosunek molowy reagentów NiCl2 : 2,2'-bpy : L-Tyr 1 : 1 : 2 3 Molar ratio of the reagents NiCl2: 2,2'-bpy: L-Tyr 1: 1: 2 3
W temperaturze pokojowej 0,119 g (0,5 mmol) chlorku niklu(II) rozpuszcza się w 5 cm3 wody 3 a następnie 0,0781 g (0,5 mmol) 2,2'-dipirydylu rozpuszcza się w 5 cm3 alkoholu metylowego. Roztwór 2,2'-dipirydylu dodaje się kroplami przy ciągłym mieszaniu do roztworu chlorku niklu(II). Powstałą mieszaninę koloru czerwonego miesza się przez 15 minut. Następnie do mieszaniny dodaje się kroplami przy ciągłym mieszaniu roztwór powstały przez rozpuszczenie 0,225 g (1 mmol) uwodnionej soli disodowej kwasu (S)-2-amino-3-(4-hydroksyfenylo)propanowego. Mieszaninę pozostawia się w temperaturze pokojowej do powolnego odparowania. Po 24 godzinach otrzymuje się ciemno szare kryształy, które odsącza się i przemywa wodą a następnie suszy na powietrzu w temperaturze pokojowej.At room temperature, 0.119 g (0.5 mmol) of nickel (II) chloride is dissolved in 5 cm 3 of water 3 and then 0.0781 g (0.5 mmol) of 2,2'-dipyridyl are dissolved in 5 cm 3 of methyl alcohol . The 2,2'-dipyridyl solution is added dropwise with constant stirring to the nickel (II) chloride solution. The resulting red mixture is stirred for 15 minutes. Then, the solution formed by dissolving 0.225 g (1 mmol) of (S) -2-amino-3- (4-hydroxyphenyl) propanoic acid disodium salt, is added dropwise to the mixture with continued stirring. The mixture is allowed to evaporate slowly at room temperature. After 24 hours, dark gray crystals are obtained which are filtered off and washed with water and then air dried at room temperature.
P r z y k ł a d 2P r z k ł a d 2
Stosunek molowy reagentów NiCl2 : 2,2'-bpy : L-Tyr 1 : 1 : 3The molar ratio of the reagents NiCl2: 2,2'-bpy: L-Tyr 1: 1: 3
Sposób otrzymywania kompleksu tri hydrat metanol di[bis((S)-2-amino-3-(4-hydroksyfenylo)propano)(2,2’-dipirydyl)nikiel(II)] o wzorze ogólnym 1, [Ni(L-Tyr)2(bpy)]2 · 3H2O · CH3OH.Method for the preparation of the complex trihydrate methanol di [bis ((S) -2-amino-3- (4-hydroxyphenyl) propano) (2,2'-dipyridyl) nickel (II)] with the general formula 1, [Ni (L- Tyr) 2 (bpy)] 2 · 3H 2 O · CH 3 OH.
33
W temperaturze pokojowej 0,119 g (0,5 mmol) chlorku niklu(II) rozpuszcza się w 5 cm3 wody 3 a następnie 0,0781 g (0,5 mmol) 2,2'-dipirydylu rozpuszcza się w 5 cm3 alkoholu metylowego. Roztwór 2,2'-dipirydylu dodaje się kroplami przy ciągłym mieszaniu do roztworu chlorku niklu(II). Powstałą mieszaninę koloru czerwonego miesza się przez 15 minut. Następnie do mieszaniny dodaje się kroplami przy ciągłym mieszaniu roztwór powstały przez rozpuszczenie 0,3375 g (1 mmol) soli disodowej kwasu (S)-2-amino-3-(4-hydroksyfenylo)propanowego. Mieszaninę pozostawia się w temperaturze pokojowej do powolnego odparowania. Po 24 godzinach otrzymuje się ciemno szare kryształy, które odsącza się i przemywa wodą a następnie suszy na powietrzu w temperaturze pokojowej.At room temperature, 0.119 g (0.5 mmol) of nickel (II) chloride is dissolved in 5 cm 3 of water 3 and then 0.0781 g (0.5 mmol) of 2,2'-dipyridyl are dissolved in 5 cm 3 of methyl alcohol . The 2,2'-dipyridyl solution is added dropwise with constant stirring to the nickel (II) chloride solution. The resulting red mixture is stirred for 15 minutes. The solution formed by dissolving 0.3375 g (1 mmol) of (S) -2-amino-3- (4-hydroxyphenyl) propanoic acid disodium salt is then added dropwise to the mixture with continued stirring. The mixture is allowed to evaporate slowly at room temperature. After 24 hours, dark gray crystals are obtained which are filtered off and washed with water and then air dried at room temperature.
Analiza elementarna dla kompleksu o wzorze ogólnym 1:Elemental analysis for the complex of general formula 1:
Obliczone dla C57H66N8O16Ni2: C, 55.37; H, 5.38; N, 9.06; Ni, 9.49 (%).Calculated for C57H66N8O16Ni2: C, 55.37; H, 5.38; N, 9.06; Ni, 9.49 (%).
Znalezione: C, 53.85; H, 5.53; N, 8.71; Ni, 9.15 (%).Found: C, 53.85; H, 5.53; N, 8.71; Ni, 9.15 (%).
Masa molowa M = 1236.56 g/mol.Molar mass M = 1236.56 g / mol.
Najważniejsze parametry strukturalne:The most important structural parameters:
Układ krystalograficzny HexagonalHexagonal crystallographic system
Grupa przestrzenna P322iSpace group P3 2 2i
Temperatura (K) 295 a/A 12.8116(18) c/A 30.035(6)Temperature (K) 295 a / A 12.8116 (18) c / A 30.035 (6)
V/A3 4269.4(12)V / A 3 4269.4 (12)
Z 3With 3
Najważniejsze pasma widma IR (cm-) 1598(vs), 1581(vs), 1563(vs), 1514(vs), 1442(vs), 1413(m), 1353(m), 1248(vs), 227 cm1M, 414 cm-1 (w).The most important bands of the IR spectrum (cm - ) 1598 (vs), 1581 (vs), 1563 (vs), 1514 (vs), 1442 (vs), 1413 (m), 1353 (m), 1248 (vs), 227 cm 1 M, 414 cm -1 (w).
PL 219 472 B1PL 219 472 B1
Związek [Ni(L-Tyr)2(bpy)]2 · 3H2O · CH3OH poddano badaniom aktywność przeciwbakteryjnej na szczepach bakterii Escherichia coli, Pseudomonas fluorescens, Serratia marcescens, Bacillus subtilis.The compound [Ni (L-Tyr) 2 (bpy)] 2 · 3H2O · CH3OH was tested for antibacterial activity on strains of Escherichia coli, Pseudomonas fluorescens, Serratia marcescens, Bacillus subtilis.
Test dla każdego szczepu bakteryjnego powtórzony był dwukrotnie. Próbę kontrolną stanowił dimetylosulfotlenek.The test for each bacterial strain was repeated twice. The control sample was dimethylsulfoxide.
Badania wykonano przy zastosowaniu metody dyfuzji badanej substancji z krążka do materiału biologicznego. Dokładny opis metody znajduje się w publikacji Synthesis, crystal structure, spectroscopic, magnetic, theoretical and microbiological studies of a nickle(II) complexes of L-tyrosine and imidazole, [Ni(lm)2(L-tyr)2 · 4H2O, A. Wojciechowska, M. Daszkiewicz, Z. Staszak, A. TruszZdybek, A. Bienko, A. Ożarowski, Inorg. Chem 2011, 50, 11532 - 11542.The research was performed using the method of diffusion of the test substance from the disc to the biological material. A detailed description of the method can be found in the publication Synthesis, crystal structure, spectroscopic, magnetic, theoretical and microbiological studies of a nickle (II) complexes of L-tyrosine and imidazole, [Ni (lm) 2 (L-tyr) 2 4H 2 O , A. Wojciechowska, M. Daszkiewicz, Z. Staszak, A. TruszZdybek, A. Bienko, A. Ożarowski, Inorg. Chem 2011, 50, 11532-11542.
T a b e l a 1. Aktywność przeciwbakteryjna związku [Ni(L-Tyr)2(bpy)]2 · 3H2O · CH3OH.a TABLE 1. Antimicrobial activity of the compound [Ni (L-Tyr) 2 (bpy)] 2 · 3H2O · CH3OH. and
a Wartość strefy zahamowania nie zawiera wartości promienia krążka; b związek wykazuje właściwości przeciwbakteryjne jeśli wartość strefy zahamowania wzrostu mikroorganizmów wynosi minimum 3 mm; c wzrost mikroorganizmów w strefie zahamowania. a The inhibition zone value does not include the disc radius value; b the compound exhibits antimicrobial properties if the zone of inhibition of microbial growth is at least 3 mm; c growth of microorganisms in the inhibition zone.
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| PL401095A PL219472B1 (en) | 2012-10-08 | 2012-10-08 | Method for producing methanol tri hydrate complex di[bis((S)-2-amino-3-(4-hydroxyphenyl)propane)(2,2 '-dipyridyl)nickel(II)] |
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| PL401095A PL219472B1 (en) | 2012-10-08 | 2012-10-08 | Method for producing methanol tri hydrate complex di[bis((S)-2-amino-3-(4-hydroxyphenyl)propane)(2,2 '-dipyridyl)nickel(II)] |
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| PL401095A1 PL401095A1 (en) | 2013-04-02 |
| PL219472B1 true PL219472B1 (en) | 2015-04-30 |
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