CN102093350A - Surface active substance using praziquantel as matrix and preparation technology thereof - Google Patents
Surface active substance using praziquantel as matrix and preparation technology thereof Download PDFInfo
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- CN102093350A CN102093350A CN2011100221937A CN201110022193A CN102093350A CN 102093350 A CN102093350 A CN 102093350A CN 2011100221937 A CN2011100221937 A CN 2011100221937A CN 201110022193 A CN201110022193 A CN 201110022193A CN 102093350 A CN102093350 A CN 102093350A
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Abstract
The invention relates to a surface active substance using praziquantel as a matrix and a preparation technology thereof. The preparation technology of the surface active substance comprises the following steps: by using a praziquantel molecule as a matrix, nitrifying to obtain nitryl praziquantel; reducing the nitryl praziquantel to obtain amino praziquantel; and under the action of catalysts, reacting with epoxy ethane, 1,2-epoxy propane, 1,2-epoxy butane, 2,3-epoxy butane and other epoxy small-molecule compounds to obtain the surface active substance. When meeting water, the surface active substance can self diffuse to form a film and float on the surface layer of the water, and has favorable effects on killing schistosome cercariae.
Description
Technical field
The present invention relates to a kind of is the surfactant and the technology of preparing thereof of parent with the praziquantel, belongs to field of fine chemical.
Background technology
Praziquantel is Chinese trade(brand)name, and its chemical name is a 2-cyclohexyl formyl radical-1,2,3,6,7, and 11b-six hydrogen-4H-pyrazine is [2,1-a] isoquinoline 99.9-4-ketone also.Under the normal temperature and pressure a kind of white or off-white color crystalline powder.Insoluble in water, be soluble in chloroform, ethanol etc.Praziquantel is one of medicine of diseases such as the linear worm of clinical treatment, schistosomicide, has easy administration, curative effect height, advantage such as untoward reaction is few.
The invention provides a kind of is the surfactant and the technology of preparing thereof of parent with the praziquantel, and this surfactant can spread on the water surface automatically, and forms the molecular film of one deck densification.This molecular film has good killing effect to parasites such as linear worm, schistosomulums.
Summary of the invention
The purpose of this invention is to provide a kind of is the surfactant and the technology of preparing thereof of parent with the praziquantel.
Surfactant involved in the present invention, be meant that with the praziquantel molecule be parent, after nitration reaction makes the nitro praziquantel, then the nitro praziquantel is reduced and make amino praziquantel, again under catalyst action, with the reaction of epoxies micromolecular compound, prepared surfactant.Epoxies small molecules wherein is meant oxyethane, 1,2 epoxy prapane, 1,2-butylene oxide ring, 2,3-butylene oxide ring etc.
The nitration reaction of passing through described in the invention prepares the nitro praziquantel, is meant in molar ratio 1 part of praziquantel under 20-40 part sulphuric acid catalysis, adds 1.0-1.2 part concentrated nitric acid, and reaction obtained the nitro praziquantel after 5-8 hour in ice bath.The nitro praziquantel reduced to prepare amino praziquantel.Concrete way is, in molar ratio with 1 part of nitro praziquantel, and 30-60 part ethanol, 5-10 part iron powder, 0.01-0.10 part hydrochloric acid, 80-100 part water, reaction is 2-5 hour under the room temperature, obtains amino praziquantel.Further the amino praziquantel with 0.01-0.03mol adds in the reactor, be heated with stirring to 60-120 ℃ after, add 0.001-0.002mol calcium phosphate and make catalyzer; stir, reactor is vacuumized the back feed nitrogen protection, triplicate; the epoxies micromolecular compound that adds 0.01-0.30mol then; isothermal reaction 24-72 hour, be cooled to room temperature, add water after; use chloroform extraction; drying is removed and is desolvated, and promptly obtains surfactant.
Through the prepared surfactant of aforesaid method, put into the water surface after, can spread automatically along the water surface immediately, and form the molecular film of one deck densification at surface layer of water, swim in surface layer of water for a long time.This molecular film can kill microorganism such as linear worm, the schistosomulum etc. that are positioned at surface layer of water, deactivation.
Embodiment
The invention will be further described below in conjunction with specific embodiment, but the present invention is not limited to following examples.
Experimental technique described in the following embodiment if no special instructions, is ordinary method.Described reagent and material all can obtain from commercial channels.
Embodiment 1
Get 1 part of praziquantel in molar ratio, add 20 parts of concentrated sulfuric acid dissolutions after, add 1 part of concentrated nitric acid again, reaction added water to precipitation and has separated out after 8 hours in ice bath, filtered, and used ethyl alcohol recrystallization, obtained the nitro praziquantel.
Get 1 part of nitro praziquantel, add 50 parts of ethanol, 8 parts of iron powders, 0.05 part of hydrochloric acid, 100 parts of water, stirring reaction is 5 hours under the room temperature, filters, and filtrate is used ethyl acetate extraction, boils off solvent, obtains amino praziquantel.
The amino praziquantel of getting 0.01mol adds in the reactor, be heated with stirring to 60 ℃ after, add 0.001mol calcium phosphate and make catalyzer; stir, reactor is vacuumized the back feed nitrogen protection, triplicate; the oxyethane that adds 0.03mol then; isothermal reaction 48 hours is cooled to room temperature, add water after; use chloroform extraction; drying is removed and is desolvated, and promptly obtains required surfactant.After resulting surfactant splashed into the water surface that contains schistosomulum, find that the mortality ratio of cercaria reaches 97% in 30 minutes.
Embodiment 2
Get 1 part of praziquantel in molar ratio, add 30 parts of concentrated sulfuric acid dissolutions after, add 1.5 parts of concentrated nitric acids again, reaction added water to precipitation and has separated out after 7 hours in ice bath, filtered, and used ethyl alcohol recrystallization, obtained the nitro praziquantel.
Get 1 part of nitro praziquantel, add 30 parts of ethanol, 10 parts of iron powders, 0.08 part of hydrochloric acid, 80 parts of water, stirring reaction is 2 hours under the room temperature, filters, and filtrate is used ethyl acetate extraction, boils off solvent, obtains amino praziquantel.
The amino praziquantel of getting 0.01mol adds in the reactor, be heated with stirring to 85 ℃ after, add 0.015mol calcium phosphate and make catalyzer; stir, reactor is vacuumized the back feed nitrogen protection, triplicate; the 1,2 epoxy prapane that adds 0.3mol then, isothermal reaction 72 hours; be cooled to room temperature; after adding water, use chloroform extraction, drying; remove and desolvate, promptly obtain required surfactant.After resulting surfactant put into the water surface that contains linear worm, find that linear worm mortality ratio reaches more than 90% in 60 minutes.
Embodiment 3
Get 1 part of praziquantel in molar ratio, add 40 parts of concentrated sulfuric acid dissolutions after, add 2 parts of concentrated nitric acids again, reaction added water to precipitation and has separated out after 5 hours in ice bath, filtered, and used ethyl alcohol recrystallization, obtained the nitro praziquantel.
Get 1 part of nitro praziquantel, add 60 parts of ethanol, 5 parts of iron powders, 0.10 part of hydrochloric acid, 90 parts of water, stirring reaction is 4 hours under the room temperature, filters, and filtrate is used ethyl acetate extraction, boils off solvent, obtains amino praziquantel.
The amino praziquantel of getting 0.01mol adds in the reactor, be heated with stirring to 120 ℃ after, add 0.020mol calcium phosphate and make catalyzer; stir, reactor is vacuumized the back feed nitrogen protection, triplicate; successively add 0.08mol butylene oxide ring and 0.02mol 1,2 epoxy prapane, isothermal reaction 24 hours; be cooled to room temperature; after adding water, use chloroform extraction, drying; remove and desolvate, promptly obtain required surfactant.Resulting surfactant is splashed into the water surface that contains schistosomulum, find that the mortality ratio of cercaria is big more than 90% in 45 minutes.
Claims (6)
1. one kind is the surfactant and the technology of preparing thereof of parent with the praziquantel, it is characterized in that: with the praziquantel molecule is parent, after nitration reaction makes the nitro praziquantel, the nitro praziquantel reduced make amino praziquantel, again under catalyst action, with the reaction of epoxies micromolecular compound, make surfactant.
2. according to claim 1ly make the nitro praziquantel, it is characterized in that through nitration reaction: in molar ratio with 1 part of praziquantel under 20-40 part sulphuric acid catalysis, add 1-2 part concentrated nitric acid, reaction obtained the nitro praziquantel after 5-8 hour in ice bath.
3. the according to claim 1 nitro praziquantel is reduced makes amino praziquantel, it is characterized in that: in molar ratio with 1 part of nitro praziquantel, and 30-60 part ethanol, 5-10 part iron powder, 0.01-0.10 part hydrochloric acid, 80-100 part water, reaction is 2-5 hour under the room temperature, obtains amino praziquantel.
4. according to claim 1 and epoxies micromolecular compound reacts, and it is characterized in that: the epoxies micromolecular compound is meant oxyethane, 1,2 epoxy prapane, 1,2-butylene oxide ring, 2,3-butylene oxide ring.
5. technology of preparing according to claim 1; it is characterized in that: the amino praziquantel of 0.01-0.03mol is added in the reactor; after being heated with stirring to 60-120 ℃; add 0.001-0.002mol calcium phosphate and make catalyzer; stir; reactor is vacuumized the back feed nitrogen protection; triplicate adds the epoxies micromolecular compound of 0.01-0.30mol, isothermal reaction 24-72 hour then; be cooled to room temperature; after adding water, use chloroform extraction, drying; remove and desolvate, promptly obtain surfactant.
6. according to the prepared surfactant of claim 5, it is characterized in that: after this surfactant is met water, but the self-diffusion film forming swims in surface layer of water, and schistosomulum is had good killing effect.
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| CN2011100221937A CN102093350A (en) | 2011-01-20 | 2011-01-20 | Surface active substance using praziquantel as matrix and preparation technology thereof |
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| CN2011100221937A CN102093350A (en) | 2011-01-20 | 2011-01-20 | Surface active substance using praziquantel as matrix and preparation technology thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565006A (en) * | 2016-11-04 | 2017-04-19 | 烟台史密得机电设备制造有限公司 | Cationic type degreaser for polymer flooding produced water treatment |
| CN109608538A (en) * | 2019-01-09 | 2019-04-12 | 江南大学 | A kind of synthetic method of praziquantel artificial antigen |
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| CN101002553A (en) * | 2006-01-20 | 2007-07-25 | 赣南师范学院 | High efficiency agent for preventing and controlling shistosomulum, and preparing technique therefor |
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2011
- 2011-01-20 CN CN2011100221937A patent/CN102093350A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101002553A (en) * | 2006-01-20 | 2007-07-25 | 赣南师范学院 | High efficiency agent for preventing and controlling shistosomulum, and preparing technique therefor |
Non-Patent Citations (3)
| Title |
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| FIONA RONKETTI ET AL.: "Praziquantel derivatives I: Modification of the aromatic ring", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
| 师华 等: "芳胺的N-烷基化反应", 《精细化工中间体》 * |
| 魏建国 等: "N，N-双（2-羟丙基）苯胺的合成", 《聚氨酯工业》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565006A (en) * | 2016-11-04 | 2017-04-19 | 烟台史密得机电设备制造有限公司 | Cationic type degreaser for polymer flooding produced water treatment |
| CN106565006B (en) * | 2016-11-04 | 2019-12-27 | 山东上禾中创科技成果转化有限公司 | Cationic oil removal agent for polymer flooding produced water treatment |
| CN109608538A (en) * | 2019-01-09 | 2019-04-12 | 江南大学 | A kind of synthetic method of praziquantel artificial antigen |
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Application publication date: 20110615 |