SU413148A1 - - Google Patents
Info
- Publication number
- SU413148A1 SU413148A1 SU1731873A SU1731873A SU413148A1 SU 413148 A1 SU413148 A1 SU 413148A1 SU 1731873 A SU1731873 A SU 1731873A SU 1731873 A SU1731873 A SU 1731873A SU 413148 A1 SU413148 A1 SU 413148A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dihydroriboflavin
- acetyl
- acetic acid
- preparation
- subjected
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229960002477 riboflavin Drugs 0.000 description 3
- 235000019192 riboflavin Nutrition 0.000 description 3
- 239000002151 riboflavin Substances 0.000 description 3
- SGSVWAYHEWEQET-SCRDCRAPSA-N 1,5-dihydroriboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2NC2=C1NC(=O)NC2=O SGSVWAYHEWEQET-SCRDCRAPSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- -1 riboflavin ester Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Изобретение относитс к способу получени новых соединений, которые могут найти применение в фармацевтическоа промышленности .This invention relates to a process for the preparation of new compounds that can be used in the pharmaceutical industry.
Известен способ получени 2,3,4.5,5-.пентаацетил-1 ,5-дигидрорибофлавина, заключаюш ,ийс в том, что рибофлавин подвергают восстановлению цинковой пылью ц среде уксусной кислоты и уксусного ангидрида.A known method for the preparation of 2,3,4.5,5-pentaacetyl-1, 5-dihydroriboflavin, implies that riboflavin is subjected to reduction by zinc dust to acetic acid and acetic anhydride.
Использование известного способа привело к получению новых соединений, смешанных эфиров 1,5-дигидрорибофлавина, имеюш,их больш:ую физиологическую активность по сравнению с известными.The use of the known method resulted in the production of new compounds, the mixed esters of 1,5-dihydroriboflavin, having their large: physiological activity compared to the known ones.
Предлагаемый способ получени смешанных эфиров 1,5-дигидрорибофлавина общей формулыThe proposed method for the preparation of the mixed esters of 1,5-dihydroriboflavin of the general formula
rHoOR rHoOR
2 2
-СОСзНг или-ССОзНг or
где R означает -COCsHs, -СОСбНб,where R means -COCsHs, -SOSbNb,
отличаетс тем, что соответствуюш ий эфир рибофлавина подвергают восстановлению цинковой нылью в среде уксусной кислоты и укcjTHoro ангидрида с последующим выделением целевого продукта известным способом.characterized in that the corresponding riboflavin ester is subjected to reduction with zinc acid in acetic acid and acetone of the anhydride, followed by isolation of the target product in a known manner.
Пример 1. 2,3,4,5,5-Тетрапропионил-5ацетил-1 ,5-дигидрорибофлавип.Example 1. 2,3,4,5,5-Tetrapropionyl-5 acetyl-1, 5-dihydroriboblavip.
0,1 г 2,3,4,5-тетрапропионилрибофлавина, 1,5 мл уксусной кислоты и 2 мл уксусного ангидрида нагревают в темноте до кииени и небольшими иорци ми нрибавл ют цинковую пыль до обесцвечивани раствора. Реакционную смесь отфильтровывают и промывают гор чей уксусной кислотой, растворитель отгон ют в вакууме. Полученное бледно-желтое масло раствор ют в хлороформе и гексаном высаживают белый аморфный осадок, еще раз раствор ют в хлороформе, раствор дважды промывают водой, затем гексаном высаживают белое вещество, центрифугируют и сушат в вакууме. Получают 0,09 г (84,1%) 2,3,4,5-тетрапропионил-5-ацетил - 1,5-дигидрорибофлавина с т. пл. 111 - 113°С.0.1 g of 2,3,4,5-tetrapropionylriboflavin, 1.5 ml of acetic acid and 2 ml of acetic anhydride are heated in the dark to shine and in small amounts zinc dust to discolor the solution. The reaction mixture is filtered and washed with hot acetic acid, the solvent is distilled off in vacuo. The resulting pale yellow oil was dissolved in chloroform and a white amorphous precipitate was precipitated with hexane, dissolved once more in chloroform, the solution was washed twice with water, then the white substance was precipitated with hexane, centrifuged and dried in a vacuum. 0.09 g (84.1%) of 2,3,4,5-tetrapropionyl-5-acetyl-1,5-dihydroriboflavin with m.p. 111 - 113 ° C.
Пример 2. 2,3,4,5-Тетрабутирил-5-ацетил-1 ,5-дигидрорибофлавин.Example 2. 2,3,4,5-Tetrabutyryl-5-acetyl-1, 5-dihydroriboflavin.
Из 0,1 г 2,3,4,5-тетрабутирилрибофлавина аналогично описанному в примере 1 получают 0,07 г (58,5%) 2,3,4,5-тетрабутирил-5-ацетил-1 ,5-дигидрорибофлавина. Пример 3. 2,3,4,5-Тетрабензоил-5-ацетил1 ,5-дигидрорибофлавин. Из 0,1 г 2,3,4,5-тетрабензоилрибофлавина аналогично описанному в примере 1 получают 0,09 г (85,7%) 2,3,4,5-тетрабензоил-5-ацеД 5-v/V ) где R означает -СОС2П5, -СОСзНу или -СОСбНб,25 отл и чающийс тем, что соответствующий эфир рибофлавина подвергают восстаROROROс т. пл. 179тил-1 ,5-дигидрорибофлавина 180°С. Предмет изобретени Способ получени смешанных эфиров 1,5дигидрорибофлавина общей формулы CH CH CR СНа Y У 114 I, новлению цинковой пылью в среде уксусной кислоты и уксусного ангидрида с последующим выделением целевого продукта известным способом.From 0.1 g of 2,3,4,5-tetrabutyrylriboflavin, as in Example 1, 0.07 g (58.5%) of 2,3,4,5-tetrabutyryl-5-acetyl-1, 5-dihydroriboflavin is obtained. Example 3. 2,3,4,5-Tetrabenzoyl-5-acetyl, 5-dihydroriboflavin. From 0.1 g of 2,3,4,5-tetrabenzoylriboflavin, similarly to that described in Example 1, 0.09 g (85.7%) of 2,3,4,5-tetrabenzoyl-5-aceD 5-v / V is obtained, where R stands for -COS2P5, -COC3Nu, or -COSbNb, 25, and is based on the fact that the corresponding riboflavin ester is subjected to a restoration. 179til-1, 5-dihydroriboflavin 180 ° C. The subject of the invention. A method for the preparation of mixed 1.5-dihydroriboflavin esters of the general formula CH CH CR CH Y V 114 I, with zinc dust in an acetic acid and acetic anhydride medium followed by isolation of the target product in a known manner.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1731873A SU413148A1 (en) | 1971-12-31 | 1971-12-31 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1731873A SU413148A1 (en) | 1971-12-31 | 1971-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU413148A1 true SU413148A1 (en) | 1974-01-30 |
Family
ID=20498335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1731873A SU413148A1 (en) | 1971-12-31 | 1971-12-31 |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU413148A1 (en) |
-
1971
- 1971-12-31 SU SU1731873A patent/SU413148A1/ru active
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