CN102417529A - S-syringin compound, synthetic method and application - Google Patents
S-syringin compound, synthetic method and application Download PDFInfo
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- CN102417529A CN102417529A CN201110258261XA CN201110258261A CN102417529A CN 102417529 A CN102417529 A CN 102417529A CN 201110258261X A CN201110258261X A CN 201110258261XA CN 201110258261 A CN201110258261 A CN 201110258261A CN 102417529 A CN102417529 A CN 102417529A
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Abstract
The invention discloses an S-syringin compound, a synthetic method and application. According to the invention, under the action of carboxy-lesterase in vivo, the S-syringin compound can be decomposed into syringin derivatives and hydrogen sulfide, which enables dual effects to be generated, thereby effectively protecting male sperms, and therefore, the S-syringin compound can treat the disease of male sterility to some extent.
Description
Technical field
The invention relates to a kind of Syringin, preparation method and use.
Background technology
Social now, owing to life stress, WP increase day by day, there is sterile symptom in the part male sex, and a kind of medicine or method of effective these diseases of treatment need be provided.
Summary of the invention
The objective of the invention is deficiency, a kind of compound, compound method and the purposes that can effectively protect mankind spermatozoon is provided to prior art.
For realizing above-mentioned purpose, the present invention has adopted following technical scheme: a kind of S-Syringin compound, and its chemical structural formula is:
A kind of compound method of described S-Syringin compound discharges group ADT-OH and the Syringin derivatives reaction obtains said S-Syringin compound with hydrogen sulfide.
The application of a kind of described S-Syringin compound in the protection mankind spermatozoon.
The application of a kind of described S-Syringin compound in treatment male sterility disease.
A kind of pharmaceutical composition that is used to protect mankind spermatozoon, it comprises described S-Syringin compound.
A kind of pharmaceutical composition that is used to treat the male sterility disease, it comprises described S-Syringin compound.
A kind of ADT-OH group, its chemical structural formula is: 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione contains under the effect of compound Procaine esterase in vivo of said ADT-OH group, can continue to discharge hydrogen sulfide.
A kind of ADT-OH group; Its chemical structural formula is: 5-(4-hydroxyphenyl)-3H-1; 2-dithiole-3-thione contains under the effect of described S-Syringin compound Procaine esterase in vivo of said ADT-OH group, can continue to discharge hydrogen sulfide.
The invention has the beneficial effects as follows: after getting into body; Under the effect of Procaine esterase, S-Syringin compound can decomposite Syringin verivate and hydrogen sulfide in vivo, produces dual function; Can effectively protect mankind spermatozoon, and then treatment male sterility disease that can be to a certain degree.
Description of drawings
Fig. 1 is the synthetic route chart of the synthetic method of S-Syringin compound of the present invention;
Embodiment
Combine accompanying drawing that the present invention is done further explain through embodiment below.
Radix Et Caulis Acanthopanacis Senticosi contains ultra oxidation disproportionation ferment SOD mixture, has good anti-oxidant function, can enhances human body immunity and the opposing radical effect of attacking.The sweet B of Radix Et Caulis Acanthopanacis Senticosi is Syringin (Syringin), is the staple of Radix Et Caulis Acanthopanacis Senticosi, and it has short sexual gland, radioprotective, fatigue-resisting function.Radix Et Caulis Acanthopanacis Senticosi can improve the sperm survival rate of different period normal males and improve each item sperm motility parameters such as motility of sperm, A level motion sperm percentage, B level motion sperm percentage, curve speed, space rate, average path speed, sperm head side oscillation amplitude.The mechanism of Radix Et Caulis Acanthopanacis Senticosi maybe can to strengthen the sperm metabolism relevant with Radix Et Caulis Acanthopanacis Senticosi.
Through discovering that hydrogen sulfide also has clear and definite anti-oxidation stress effect in testis tissue.The pretreated mouse of hydrogen sulfide have tangible enhancing spermatid opposing high temperature (43 ℃, oxidative stress damage and apoptotic effect due to 30min).This experimental result prompting hydrogen sulfide has the protection spermatid, promotes the effect of its generation and growth.
The present invention transforms the chemical structure of Syringin, adds a group that can discharge hydrogen sulfide, makes it to become S-Syringin compound, stablizes in vivo to discharge hydrogen sulfide, will produce dual therapeutic action together with the Syringin verivate.This design can produce dual sperm provide protection.
5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione (ADT-OH) are that hydrogen sulfide discharges group, and under the effect of Procaine esterase in vivo, the compound that contains the ADT-OH group can continue to discharge hydrogen sulfide.
Among the present invention, the ADT-OH group is combined with Syringin (syringin), produce S-Syringin (S-syringin) compound.After getting into body, S-Syringin compound can decomposite Syringin verivate and hydrogen sulfide under the effect of Procaine esterase, thereby produces dual function.
The synthetic route of S-Syringin (S-syringin) compound can be as shown in Figure 1:
Syringic aldehyde and 2,3,4,6-tetrem acyloxy-alpha-D-Glucopyranose bromide room temperature reaction under silver suboxide, quinoline condition obtains intermediate compound 1; Reaction obtains intermediate compound 2 to intermediate compound 1 with propanedioic acid; Intermediate compound 2 stirred overnight at room temperature in the methanol solution of sodium methylate obtains intermediate compound 3; Intermediate compound 3 obtains S-Syringin compound with the ADT-OH radical reaction, and this reaction conditions is that DCC (NSC 57182) does that condensing agent, DMAP (4-dimethylaminopyridine) are made catalyzer, methylene dichloride is a solvent.
Above content is to combine concrete embodiment to the further explain that the present invention did, and can not assert that practical implementation of the present invention is confined to these explanations.For the those of ordinary skill of technical field under the present invention, under the prerequisite that does not break away from the present invention's design, can also make some simple deduction or replace, all should be regarded as belonging to protection scope of the present invention.
Claims (9)
1. S-Syringin compound, its chemical structural formula is:
2. the compound method of the described S-Syringin of claim 1 compound discharges hydrogen sulfide that group ADT-OH and Syringin verivate are synthetic to obtain said S-Syringin compound.
3. compound method as claimed in claim 2; It is characterized in that: said synthetic route is to be that raw material obtains intermediate compound 1, intermediate compound 2, intermediate compound 3 in order with the syringic aldehyde; Intermediate compound 3 obtains the purple fourth glycoside compound of said S-with said ADT-OH reaction
The chemical structural formula of intermediate compound 1 is:
The chemical structural formula of intermediate compound 2 is:
The chemical structural formula of intermediate compound 3 is:
4. the application of the described S-Syringin of claim 1 compound in the protection mankind spermatozoon.
5. the application of the described S-Syringin of claim 1 compound in treatment male sterility disease.
6. pharmaceutical composition that is used to protect mankind spermatozoon, it comprises the described S-Syringin of claim 1 compound.
7. pharmaceutical composition that is used to treat the male sterility disease, it comprises the described S-Syringin of claim 1 compound.
8. ADT-OH group, its chemical structural formula is: 5-(4-hydroxyphenyl)-3H-1,2-dithiole-3-thione contains under the effect of compound Procaine esterase in vivo of said ADT-OH group, can continue to discharge hydrogen sulfide.
9. ADT-OH group; Its chemical structural formula is: 5-(4-hydroxyphenyl)-3H-1; 2-dithiole-3-thione contains under the effect of the described S-Syringin of claim 1 compound Procaine esterase in vivo of said ADT-OH group, can continue to discharge hydrogen sulfide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110258261XA CN102417529A (en) | 2011-09-02 | 2011-09-02 | S-syringin compound, synthetic method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110258261XA CN102417529A (en) | 2011-09-02 | 2011-09-02 | S-syringin compound, synthetic method and application |
Publications (1)
| Publication Number | Publication Date |
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| CN102417529A true CN102417529A (en) | 2012-04-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| CN201110258261XA Withdrawn CN102417529A (en) | 2011-09-02 | 2011-09-02 | S-syringin compound, synthetic method and application |
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| CN (1) | CN102417529A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103735571A (en) * | 2013-12-17 | 2014-04-23 | 南京医科大学 | Application of hydrogen sulfide and donor thereof in improving sperm quality and function |
| CN115960075A (en) * | 2021-10-08 | 2023-04-14 | 深圳枫语生物医药科技有限公司 | Caffeic acid derivative and preparation method and application thereof |
-
2011
- 2011-09-02 CN CN201110258261XA patent/CN102417529A/en not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103735571A (en) * | 2013-12-17 | 2014-04-23 | 南京医科大学 | Application of hydrogen sulfide and donor thereof in improving sperm quality and function |
| CN103735571B (en) * | 2013-12-17 | 2016-04-27 | 南京医科大学 | Hydrogen sulfide and donor thereof are improving the application in sperm quality and function |
| CN115960075A (en) * | 2021-10-08 | 2023-04-14 | 深圳枫语生物医药科技有限公司 | Caffeic acid derivative and preparation method and application thereof |
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Application publication date: 20120418 |