CN108484528B - With the active organic selenium class compound of resisting oxidation free radical and its synthetic method and application - Google Patents
With the active organic selenium class compound of resisting oxidation free radical and its synthetic method and application Download PDFInfo
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Abstract
The present invention relates to the active organic selenium class compound of resisting oxidation free radical, the chemical name of the organic selenium class compound are as follows: 2- (4- (4- amino-phenyl)-seleno)-phenyl -1,2- benzisoxa selenazoles -3 (2H) -one, the organic selenium class compound synthesis method is simple, reaction condition is easily controllable, and reaction raw materials are cheap and easy to get, and the organic selenium class compound has apparent resisting oxidation free radical effect, to hydrogen peroxide (H2O2) and peroxynitrite (ONOO‑) free radical all shows preferable scavenging effect, it is expected to become medicine resisting oxidation free radical；In addition, selenium element is the essential trace elements of the human body, there is the active seleno phenyl Benzisoelenazolone class compound of resisting oxidation free radical, raw material is easy to get, is readily synthesized, and has the value of further investigation exploitation.
Description
Technical field
The present invention relates to pharmaceutical chemical synthesis technical fields, specifically have resisting oxidation free radical active organic
Selenium class compound and its synthetic method and application.
Background technique
Free radical, and it is properly termed as free radical, refer to atom, atomic group or special that out orbit contains unpaired electron
The molecule of state.Because the out orbit of free radical has into single electronics, their chemical property is extremely active.Oxygen exists
It is essential in the vital movement of all aerobic animals, is also particularly important particularly with surviving for the mankind.In oxo
During thanking, a large amount of hydrogen peroxide (H is generated first2O2), secondly generate a large amount of ultra-oxygen anion free radical (O2 -),
In addition also generate a certain amount of hydroxyl radical free radical (HO) and singlet oxygen (1O2), the object of these metabolins and other oxidisability
Matter such as hypochlorous acid (HClO) etc. is collectively referred to as active oxygen (ROS).It can be seen that free radical results from organism metabolic activity
In the process, wherein O2 -·、HO·、H2O2, nitric oxide (NO), alicyclic diradical (ROO), peroxynitrite
(ONOO-) important free radical representative during vital movement.Scientists study discovery, these free radicals and the mankind
Aging and a variety of diseases have inseparable relationship, and during physical exertion various normal physiological functions
Adjusting cell signalling is played, the functions such as immune metabolism are enhanced.Therefore, medically it is to the demand of medicine resisting oxidation free radical
Urgent.
Selenium is one of the essential trace elements of the human body, is the constituent of the biological enzyme such as GPX, and the effect of this enzyme is that catalysis is gone back
The redox reaction of originality glutathione (GSH) and peroxide are important free radical so antioxidation can be played
Scavenger.
Continuous attention with people to oxidative stress diseases, the biological study about organic selenium compounds increasingly increase
It is more, it was found that a batch has the active small molecule organic selenium compounds of GPX bionic enzyme.Wherein, ebselen (Ebselen) is exactly
One typical example.Ebselen is the organic selenium compounds with GPX sample effect, can remove lipid peroxy free radical, suppression
Its damage to DNA is made, very strong anti-inflammatory, antimycotic isoreactivity is all shown in inflammation model.
The mechanism that ebselen removes hydroperoxides is similar to GPX enzyme, can be in vivo in the presence of GSH reducing agent
A series of hydroperoxides (ROOH, H in vivo are removed in catalysis2O2), and pass through redox " ping-pong mechanism ", finally by H2O2
It is reduced into water.The mechanism participates in the redox equilibrium in regulation mammalian cell.
Most of organic selenium compounds all have the feature of the above redox characteristic and GPX sample activity.However, research hair
Existing ebselen is to H2O2The scavenging effect of free radical is obvious, and to ONOO-The elimination effect of free radical is unobvious；Hexichol selenide
To ONOO-The elimination effect of free radical is obvious, to H2O2The scavenging effect of free radical is unobvious.Two kinds of compounds are by internal paddy
The regulation of the sweet peptide of Guang, is presented reversible redox reaction.But two kinds of compounds are to reactive oxygen species (ROS) free radical and work
Property nitrogen material (RNS) free radical removing in have significant difference.In practical application, medicine resisting oxidation free radical is come
It says, it can be more desirable to there is scavenging effect simultaneously to reactive oxygen species (ROS) free radical and reactive nitrogen species (RNS) free radical
Compound.
Summary of the invention
In order to solve the above-mentioned technical problems, the present invention provides with the active organic selenium class compound of resisting oxidation free radical
And its synthetic method and application, the organic selenium class compound synthesis method is simple, reaction condition is easily controllable, and reaction raw materials valence
It is honest and clean to be easy to get, there is apparent resisting oxidation free radical effect, to hydrogen peroxide (H2O2) and peroxynitrite (ONOO-)
Free radical all shows preferable scavenging effect.
The technical solution that the present invention uses to solve above-mentioned technical problem are as follows: there is the active organic selenium of resisting oxidation free radical
Class compound, the chemical name of the organic selenium class compound are as follows: 2- (4- (4- amino-phenyl)-seleno)-phenyl -1,2- benzo
Different selenazoles -3 (2H) -one, structural formula are as follows:
Synthetic method with the active organic selenium class compound of resisting oxidation free radical, the synthetic method specifically include as follows
Step:
Step 1: iodo: taking sodium bicarbonate to be configured to 500~750ml of saturated solution of sodium bicarbonate, later, 5~25
In DEG C temperature range, under nitrogen protection and under the conditions of being stirred continuously, it is added 0.5 into the saturated solution of sodium bicarbonate of preparation~
Then 1.05 moles of aniline is added portionwise 0.5~1.05 mole of iodine powder and is reacted, until obtain solid be precipitated completely and
The clear solidliquid mixture of supernatant, is filtered later, and gained filter residue is dried in vacuo under the conditions of 3~5 DEG C, is made solid
Body paraiodoaniline, it is spare.
Step 2: selenide: paraiodoaniline made from step 1 being added in the DMSO solvent of 500~1000ml, sufficiently
Stirring later, 0.01~0.05 mole of Cu is sequentially added into gained mixed solution to being completely dissolved2O, 0.01~0.05
Mole ethylenediamine and 0.01~0.05 mole of KOH be then heated to 100~200 DEG C, and 0.5 is added thereto
~1.05 moles of selenium powder carries out reaction 1~for 24 hours under constant agitation, later, gained reaction product is poured into 5~
In 10L ice water, after solid is precipitated completely, filtering, and gained filter residue is dried under the conditions of less than 100 DEG C, it is made solid
Body two-(p-aminophenyl)-selenide, it is spare.
Step 3: condensation: the second by 200~500mL being added into made from step 2 two-(p-aminophenyl)-selenides
The mixed solvent of the water of ether and 200~500mL composition, is stirred well to after being completely dissolved, and 0.5~1.05 mole of 2- chlorine is added
Seleno chlorobenzoyl chloride is stirred to react 2~12h in -5~35 DEG C of temperature ranges, after solid is precipitated completely, filtering, and by institute
It obtains filter residue to be dried under the conditions of less than 100 DEG C, solid 2- (4- (4- amino-phenyl)-seleno)-phenyl -1,2- benzene is made
And different -3 (2H) -one of selenazoles has the active organic selenium class compound of resisting oxidation free radical to get finished product.
As described above there is the active organic selenium class compound of resisting oxidation free radical to prepare medicine resisting oxidation free radical
In application.
As a preferred embodiment, the iodine powder being added portionwise described in step 1 is fine-powdered, adding manner be every 2~
3min is added once, and 20~40min is added.
As a preferred embodiment, microwave heating is heated to be described in step 2, microwave heating temperature is 100~160 DEG C, instead
It is 0.5~3h between seasonable.
As a preferred embodiment, it is heated to be described in step 2 and is heated at reflux, being heated at reflux temperature is 120~180 DEG C, instead
Between seasonable for 12~for 24 hours.
As a preferred embodiment, in step 3, the ether of addition and the volume ratio of water are ether: water=1:1.
As a preferred embodiment, it in step 3, is added after mixed solvent, is additionally added the potassium carbonate of 50-300g.
Compared with prior art, the invention has the following advantages:
(1) the present invention provides with the active organic selenium class compound of resisting oxidation free radical and its synthetic method and answer
With using aniline as starting material, by iodo, selenideization and condensation three-step reaction obtain 2- (4- (4- amino-phenyl)-selenium
Generation)-phenyl -1,2- benzisoxa selenazoles -3 (2H) -one, synthetic method is simple, reaction condition is easily controllable, and reaction raw materials are inexpensive
It is easy to get；
(2) the present invention provides with the active organic selenium class compound of resisting oxidation free radical and its synthetic method and answer
With the organic selenium class compound has apparent resisting oxidation free radical effect, to hydrogen peroxide (H2O2) and peroxynitrite yin
Ion (ONOO-) free radical all shows preferable scavenging effect, it is expected to become medicine resisting oxidation free radical；In addition, selenium element
It is the essential trace elements of the human body, there is the active seleno phenyl Benzisoelenazolone class compound of resisting oxidation free radical, raw material
It is easy to get, is readily synthesized, there is the value of further investigation exploitation.
Specific embodiment
The present invention will be described in detail below with reference to specific embodiments, the present embodiment based on the technical solution of the present invention,
The detailed implementation method and specific operation process are given.
With the active organic selenium class compound of resisting oxidation free radical, the chemical name of the organic selenium class compound are as follows: 2-
(4- (4- amino-phenyl)-seleno)-phenyl -1,2- benzisoxa selenazoles -3 (2H) -one, structural formula are as follows:
Synthetic method as described above with the active organic selenium class compound of resisting oxidation free radical, synthetic method tool
Body includes the following steps:
Step 1: iodo: taking sodium bicarbonate to be configured to 500~750ml of saturated solution of sodium bicarbonate, later, 5~25
In DEG C temperature range, under nitrogen protection and under the conditions of being stirred continuously, it is added 0.5 into the saturated solution of sodium bicarbonate of preparation~
Then 1.05 moles of aniline is added portionwise 0.5~1.05 mole of iodine powder and is reacted, the iodine powder being added portionwise is thin
Powdery, adding manner are to be added every 2~3min primary, and 20~40min is added, and are precipitated completely and supernatant until obtaining solid
Clear solidliquid mixture, is filtered later, and gained filter residue is dried in vacuo under the conditions of 3~5 DEG C, and solid is made to iodine
Aniline, it is spare.
Step 2: selenide: paraiodoaniline made from step 1 being added in the DMSO solvent of 500~1000ml, sufficiently
Stirring later, 0.01~0.05 mole of Cu is sequentially added into gained mixed solution to being completely dissolved2O, 0.01~0.05
Mole ethylenediamine and 0.01~0.05 mole of KOH be then heated to 100~200 DEG C, the microwave that is heated to be adds
Heat is heated at reflux, and temperature is 100~160 DEG C when microwave heating, and the reaction time is 0.5~3h.Preferably, microwave heating
Temperature is 120 DEG C, reaction time 1h.When being heated at reflux temperature be 120~180 DEG C, the reaction time be 12~for 24 hours.And to its
It is middle that 0.5~1.05 mole of selenium powder is added, under constant agitation, reaction 1~for 24 hours is carried out, later, by gained reaction product
It is poured into 5~10L ice water, after solid is precipitated completely, filtering, and gained filter residue is dried under the conditions of less than 100 DEG C,
Two-(p-aminophenyl)-selenide of solid is made, it is spare.
Step 3: condensation: the second by 200~500mL being added into made from step 2 two-(p-aminophenyl)-selenides
The mixed solvent of the water of ether and 200~500mL composition, preferably, the volume ratio of the ether and water that are added is ether: water=
1:1.It is added after mixed solvent, is additionally added the potassium carbonate of 50-300g, is stirred well to after being completely dissolved, addition 0.5~
1.05 moles of 2- chlorine seleno chlorobenzoyl chloride is stirred to react 2~12h in -5~35 DEG C of temperature ranges, is precipitated completely to solid
Afterwards, it filters, and gained filter residue is dried under the conditions of less than 100 DEG C, solid 2- (4- (4- amino-phenyl)-selenium is made
Generation)--3 (2H) -one of phenyl -1,2- benzisoxa selenazoles to get finished product have the active organic selenium class chemical combination of resisting oxidation free radical
Object.
Synthetic route with the active organic selenium class compound of resisting oxidation free radical is as follows:
As described above there is the active organic selenium class compound of resisting oxidation free radical to prepare medicine resisting oxidation free radical
In application.
Embodiment one
(1) NaHCO is added in the beaker of 1L360g (0.7mol) and 500ml water, are vigorously stirred at 12 DEG C, make
NaHCO3Sufficiently dissolution；Then aniline 45g (0.5mol) is added, to prevent aniline to be oxidized by oxygen, quickly by the simple substance of grinding
Iodine powder 130g (0.5mol) is added portionwise, and every 2min plus once, about 20min is added in total, to ensure that iodine is sufficiently anti-
It should agglomerate without accumulating, continue stirring 20min and taken off to the greatest extent to iodine color, clarification is presented in solution, and paraiodoaniline is with the shape of dark precipitate
Formula is precipitated, and filters airing and obtains crude product.It will be added to absolute ethanol in crude product, stirring makes it sufficiently dissolve formation at 65 DEG C
Then saturated solution filters and obtains the ethanol solution of clear paraiodoaniline；Suitable deionized water is added, cooling is protected from light,
Colourless acicular crystal is recrystallized to obtain, it is dry under the conditions of 3 DEG C using vacuum and low temperature to prevent it to be oxidized, purification pair can be obtained
Iodoaniline, yield 51%.
(2) selenium powder (40g, 0.5mol) is added to paraiodoaniline made from step 1, Cu2O (1.4g, 0.01mol), second two
Amine (0.6g, 0.01mol), KOH (12g, 0.01mol), DMSO (500mL), 100 DEG C of microwave reactions, 0.5h.End of reaction is poured into
It in 5L ice water, stirs, filtering is washed solid with massive laundering, is drying to obtain, yield 82%.
(3) two-p-aminophenyl selenides made from step 2 are placed in 1500ml three-necked bottle, be added 200ml water and
200ml ether, K2CO350g.Slowly it is added dropwise compound 2- chlorine seleno chlorobenzoyl chloride 105g's (0.5mol) under ice bath cooling condition
Diethyl ether solution 200ml, milk yellow precipitating generate, then in -5 DEG C of stir about 2h, filter later, filter residue is taken gradually to use unsaturated carbonate
Hydrogen sodium solution and purified water cleaning repeatedly, recrystallize to obtain pale yellow crystals with dehydrated alcohol after drying.Yield 95%.
Embodiment two
(1) NaHCO is added in the beaker of 2L3120g (1.4mol) and 750ml water, are vigorously stirred at 15 DEG C, make
NaHCO3Sufficiently dissolution；Then aniline 91g (1.05mol) is added, to prevent aniline to be oxidized by oxygen, quickly by the simple substance of grinding
Iodine powder 200g (0.75mol) is added portionwise, and every 3min plus once, about 30min is added in total, to ensure that iodine is sufficiently anti-
It should agglomerate without accumulating, continue stirring 40min and taken off to the greatest extent to iodine color, clarification is presented in solution, and paraiodoaniline is with the shape of dark precipitate
Formula is precipitated, and filters airing and obtains crude product.It will be added to absolute ethanol in crude product, stirring makes it sufficiently dissolve formation at 75 DEG C
Then saturated solution filters and obtains the ethanol solution of clear paraiodoaniline；Suitable deionized water is added, cooling is protected from light,
Colourless acicular crystal is recrystallized to obtain, it is dry under the conditions of 5 DEG C using vacuum and low temperature to prevent it to be oxidized, purification pair can be obtained
Iodoaniline, yield 59%.
(2) selenium powder (80g, 1.05mol) is added in paraiodoaniline made from step 1, Cu2O (7g, 0.05mol), ethylenediamine
(3g, 0.05mol), KOH (30g, 0.05mol), DMSO (1000mL), 180 DEG C of back flow reactions, for 24 hours.End of reaction is poured into 10L
It in ice water, stirs, filtering washs solid with massive laundering, is drying to obtain two-to amino-diphenyl selenide, yield 86%.
(3) two-p-aminophenyl selenides made from step 2 are placed in 5000ml three-necked bottle, be added 500ml water and
500ml ether.The diethyl ether solution of compound 2- chlorine seleno chlorobenzoyl chloride 210g (1.05mol) is slowly added dropwise under ice bath cooling condition
500ml, milk yellow precipitating generate, then in 35 DEG C of stir about 12h, then filter, filter residue is taken gradually to use saturated sodium bicarbonate molten
Liquid and purified water cleaning repeatedly, recrystallize to obtain pale yellow crystals with dehydrated alcohol after drying.Yield 97%.
Embodiment three
(1) NaHCO is added in the beaker of 2L3100g (1.2mol) and 600ml water, are vigorously stirred at 15 DEG C, make
NaHCO3Sufficiently dissolution；Then aniline 90g (1.00mol) is added, to prevent aniline to be oxidized by oxygen, quickly by the simple substance of grinding
Iodine powder 230g (0.95mol) is added portionwise, and every 3min plus once, about 30min is added in total, to ensure that iodine is sufficiently anti-
It should agglomerate without accumulating, continue stirring 40min and taken off to the greatest extent to iodine color, clarification is presented in solution, and paraiodoaniline is with the shape of dark precipitate
Formula is precipitated, and filters airing and obtains crude product.It will be added to absolute ethanol in crude product, stirring makes it sufficiently dissolve formation at 70 DEG C
Then saturated solution filters and obtains the ethanol solution of clear paraiodoaniline；Suitable deionized water is added, cooling is protected from light,
Colourless acicular crystal is recrystallized to obtain, it is dry under the conditions of 4 DEG C using vacuum and low temperature to prevent it to be oxidized, purification pair can be obtained
Iodoaniline, yield 58%.
(2) selenium powder (40g, 0.5mol) is added in paraiodoaniline made from step 1, Cu2O (7g, 0.05mol), ethylenediamine
(3g, 0.05mol), KOH (30g, 0.05mol), DMSO (1000mL), 120 DEG C of microwave reactions, 1h.End of reaction is poured into 10L
It in ice water, stirs, filtering washs solid with massive laundering, is drying to obtain two-to amino-diphenyl selenide, yield 90%.
(3) two-p-aminophenyl selenides made from step 2 are placed in 3000ml three-necked bottle, be added 300ml water and
300ml ether, K2CO3300g.Compound 2- chlorine seleno chlorobenzoyl chloride 165g (0.75mol) is slowly added dropwise under ice bath cooling condition
Diethyl ether solution 300ml, milk yellow precipitating generate, then in 15 DEG C of stir about 6h, then filter, filter residue taken gradually to use saturated carbon
Sour hydrogen sodium solution and purified water cleaning repeatedly, recrystallize to obtain pale yellow crystals with dehydrated alcohol after drying.Yield 98%.
Experimental study data
The present invention provides with the active organic selenium class compound of resisting oxidation free radical and its synthetic method and application, it is somebody's turn to do
Organic selenium class compound has apparent resisting oxidation free radical effect, to hydrogen peroxide (H2O2) and peroxynitrite
(ONOO-) free radical all shows preferable scavenging effect, and specific data is shown in Table 1:
Table 1 has the resisting oxidation free radical activity of the active organic selenium class compound of resisting oxidation free radical
As shown in Table 1, there is the active organic selenium class chemical combination of resisting oxidation free radical using synthetic method of the present invention synthesis
Object has apparent resisting oxidation free radical effect, to hydrogen peroxide (H2O2) and peroxynitrite (ONOO-) free radical
Preferable scavenging effect is all shown, is expected to become medicine resisting oxidation free radical.
The above described is only a preferred embodiment of the present invention, be not intended to limit the present invention in any form, though
So the present invention is as above with preferred embodiment description, and however, it is not intended to limit the invention, any technology people for being familiar with this profession
Member, without departing from the scope of the present invention, when a little change or modification made using technology contents described above
It is the equivalent embodiment of equivalent variations, but without departing from the technical solutions of the present invention, according to the technical essence of the invention
Any simple modification, equivalent change and modification to the above embodiments, all of which are still within the scope of the technical scheme of the invention.
Claims (8)
1. having the active organic selenium class compound of resisting oxidation free radical, it is characterised in that: the chemistry of the organic selenium class compound
Title are as follows: 2- [(4- (4- amino-phenyl)-seleno)-phenyl] -1,2- benzisoxa selenazoles -3 (2H) -one, structural formula are as follows:
。
2. as described in claim 1 with the synthetic method of the active organic selenium class compound of resisting oxidation free radical, feature
Be: the synthetic method specifically comprises the following steps:
Step 1: iodo:
Sodium bicarbonate is taken to be configured to 500~750ml of saturated solution of sodium bicarbonate, later, in 5~25 DEG C of temperature ranges, nitrogen
Under gas shielded and under the conditions of being stirred continuously, 0.5~1.05 mole of aniline is added into the saturated solution of sodium bicarbonate of preparation, so
0.5~1.05 mole of iodine powder is added portionwise afterwards to be reacted, is precipitated completely and the clear solid-liquid of supernatant until obtaining solid
Mixture filters later, and gained filter residue is dried in vacuo under the conditions of 3~5 DEG C, and solid paraiodoaniline is made, spare；
Step 2: selenide:
Paraiodoaniline made from step 1 is added in the DMSO solvent of 500~1000ml, is stirred well to and is completely dissolved, it
Afterwards, 0.01~0.05 mole of Cu is sequentially added into gained mixed solution2O, 0.01~0.05 mole of ethylenediamine and 0.01
Then~0.05 mole of KOH is heated to 100~200 DEG C, and 0.5~1.05 mole of selenium powder is added thereto,
Under the conditions of being stirred continuously, reaction 1~for 24 hours is carried out, later, gained reaction product is poured into 5~10L ice water, it is complete to solid
After precipitation, filtering, and gained filter residue is dried under the conditions of less than 100 DEG C, two-(p-aminophenyl)-selenium of solid is made
Ether, it is spare；
Step 3: condensation:
The ether and 200~500mL by 200~500mL are added into made from step 2 two-(p-aminophenyl)-selenides
The mixed solvent of water composition, is stirred well to after being completely dissolved, and 0.5~1.05 mole of 2- chlorine seleno chlorobenzoyl chloride is added ,-
In 5~35 DEG C of temperature ranges, it is stirred to react 2~12h, after solid is precipitated completely, filtering, and by gained filter residue less than 100
It is dried under the conditions of DEG C, solid 2- [(4- (4- amino-phenyl)-seleno)-phenyl] -1,2- benzisoxa selenazoles -3 is made
(2H) -one has the active organic selenium class compound of resisting oxidation free radical to get finished product.
3. as claimed in claim 2 with the synthetic method of the active organic selenium class compound of resisting oxidation free radical, feature
Be: the iodine powder being added portionwise described in step 1 is fine-powdered, and adding manner is that primary, 20~40min is added every 2~3min
It adds.
4. as claimed in claim 2 with the synthetic method of the active organic selenium class compound of resisting oxidation free radical, feature
It is: is heated to be microwave heating described in step 2, microwave heating temperature is 100~160 DEG C, and the reaction time is 0.5~3h.
5. as claimed in claim 2 with the synthetic method of the active organic selenium class compound of resisting oxidation free radical, feature
Be: being heated to be described in step 2 and be heated at reflux, be heated at reflux temperature be 120~180 DEG C, the reaction time be 12~for 24 hours.
6. as claimed in claim 2 with the synthetic method of the active organic selenium class compound of resisting oxidation free radical, feature
Be: in step 3, the ether of addition and the volume ratio of water are ether: water=1:1.
7. as claimed in claim 2 with the synthetic method of the active organic selenium class compound of resisting oxidation free radical, feature
It is: in step 3, is added after mixed solvent, is additionally added the potassium carbonate of 50-300g.
8. described in claim 1 there is the active organic selenium class compound of resisting oxidation free radical to prepare resisting oxidation free radical medicine
Application in object.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1704410A (en) * | 2004-05-31 | 2005-12-07 | 北京大学 | Benzoisoselenothiazolidone derivatives and their preparing process and use |
| CN101019863A (en) * | 2007-03-20 | 2007-08-22 | 陕西师范大学 | Application of 2-phenyl-1, 2-benzoisoselenazole-3(2H)-tone in preparing medicine for resisting sports fatigue |
Family Cites Families (1)
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| US6984636B2 (en) * | 2002-08-12 | 2006-01-10 | Medical Research Council | Mitochondrially targeted antioxidants |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1704410A (en) * | 2004-05-31 | 2005-12-07 | 北京大学 | Benzoisoselenothiazolidone derivatives and their preparing process and use |
| CN101019863A (en) * | 2007-03-20 | 2007-08-22 | 陕西师范大学 | Application of 2-phenyl-1, 2-benzoisoselenazole-3(2H)-tone in preparing medicine for resisting sports fatigue |
Non-Patent Citations (1)
| Title |
|---|
| Synthesis, Structure, and Glutathione Peroxidase-Like Activity of Amino Acid Containing Ebselen Analogues and Diaryl Diselenides;Karuthapandi Selvakumar et al.;《Chem. Eur. J.》;20111231;第17卷;12741-12755 * |
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