CN102942544B - Nepetalactone trifluoromethyl benzoate as well as preparation process and use of nepetalactone trifluoromethyl benzoate - Google Patents
Nepetalactone trifluoromethyl benzoate as well as preparation process and use of nepetalactone trifluoromethyl benzoate Download PDFInfo
- Publication number
- CN102942544B CN102942544B CN201210523879.9A CN201210523879A CN102942544B CN 102942544 B CN102942544 B CN 102942544B CN 201210523879 A CN201210523879 A CN 201210523879A CN 102942544 B CN102942544 B CN 102942544B
- Authority
- CN
- China
- Prior art keywords
- schizonepetolactone
- methyl benzoate
- trifluoro methyl
- domestic
- nepetalactone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a nepetalactone trifluoromethyl benzoate as well as a preparation process and use of nepetalactone trifluoromethyl benzoate. The nepetalactone trifluoromethyl benzoate is characterized in that the molecular formula is C18H17F3O4 and the melting point is 177-178 DEG C; and the specific rotation of the nepetalactone trifluoromethyl benzoate is as shown in the specification. The invention also discloses a method for extracting the nepetalactone trifluoromethyl benzoate, and application of nepetalactone trifluoromethyl benzoate in preparation of an anti-common cold virus medicament.
Description
Technical field
The present invention relates to a kind of Schizonepetolactone trifluoro methyl benzoate and preparation technology and purposes, belong to technical field of medicine.
Background technology
Schizonepetolactone (C
10h
14o
3) for extract a kind of Loliolide obtaining in Chinese medicinal materials schizonepeta,, be colourless grain brilliant (ethyl acetate), mp:188～189 ℃.TLC aobvious red (10% sulfuric acid ethanol), molecular formula is C
10h
14o
3, its structural formula is
Chinese patent CN01108186.4 has disclosed structure collection of illustrative plates of Schizonepetolactone and uses thereof, it can be used for preparing anti-cold medicine, anti-inflammation drugs, antibacterials, analgesic agent etc., Chinese patent CN201010217622.1 has disclosed a kind of improvement preparation technology of Schizonepetolactone, and preparation manipulation simplification, yield raising, the production cost of Schizonepetolactone are reduced.But Schizonepetolactone in vitro infected by influenza reactive force a little less than, in order to obtain the medicine of stronger resisiting influenza virus effect, intend by structure of modification, to obtain, there is the sick active Schizonepetolactone derivative of stronger In Vitro Anti influenza.But up to now, not yet there is report by Schizonepetolactone, after trifluoro methyl benzoate, to be obtained Schizonepetolactone trifluoro methyl benzoate.
Summary of the invention
The object of the present invention is to provide and a kind ofly by Schizonepetolactone, after trifluoro methyl benzoate, obtained Schizonepetolactone trifluoro methyl benzoate and its preparation method and as the purposes of medicine.
Technical scheme of the present invention is as following
Schizonepetolactone trifluoromethyl benzonitrile acid esters, is characterized in that molecular formula is C
18h
17f
3o
4, fusing point is 177-178 ℃, and its specific optical rotation is=and+41.2 ° (c 1.0, CH
3oH), its structural formula is as follows, the temporary called after Schizonepetolactone of inventor trifluoro methyl benzoate:
Schizonepetolactone trifluoro methyl benzoate preparation method of the present invention comprises the steps:
A. get Schizonepetolactone, appropriate to trifluoromethylbenzoic acid and DMAP (DMAP), these three kinds of material amount of substance ratios are 0.5～1.5: 1.5～2.5: 0.5～1.5, be placed in reaction vessel, add methylene dichloride, stirring is dissolved it completely, add N, N '-dicyclohexylcarbodiimide (DCC) or 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride (EDCI), these two kinds of material amount of substances are 1.5～2.5 times of Schizonepetolactone, in room temperature reaction, TLC checks reaction end, obtains reaction solution;
B. by A step gained reaction solution, drip methyl alcohol and make solution clarification, add silica gel, underpressure distillation solvent, to dry, obtains silica gel compound sample;
C. the silica obtained compound sample dress of B step post is carried out to column chromatography, with the petroleum ether-ethyl acetate that volume proportion is 4～7: 1, carry out wash-out, stream part that collection contains Schizonepetolactone trifluoro methyl benzoate, reclaim under reduced pressure elutriant after merging, can obtain Schizonepetolactone trifluoro methyl benzoate white crystalline powder.
The preparation method of Schizonepetolactone trifluoro methyl benzoate in above-mentioned steps A, Schizonepetolactone, is 1: 2: 1 to trifluoromethylbenzoic acid and three kinds of material amount of substance ratios of DMAP; The N adding, N '-dicyclohexylcarbodiimide or 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride, these two kinds of material amount of substances are 2 times of Schizonepetolactone; The volume proportion of step C PetroChina Company Limited. ether-ethyl acetate is 5: 1.
The In Vitro Anti influenza virus pharmacodynamics test of Schizonepetolactone trifluoro methyl benzoate shows, it has good anti-H
3n
2activity, therefore can be used for preparing anti-influenza virus medicament.
Schizonepetolactone trifluoro methyl benzoate of the present invention is a kind of new menthane type monoterpenes compound, and simple in structure, preparation method is easy to be inexpensive, and has stronger physiologically active.
Accompanying drawing explanation
The ultraviolet spectrogram of Fig. 1 compound Schizonepetolactone trifluoro methyl benzoate, λ max:225.0nm, prompting compound has conjugation Absorption Characteristics
The HPLC purity collection of illustrative plates of Fig. 2 compound Schizonepetolactone trifluoro methyl benzoate, it is 97.0% that normalization method calculates Schizonepetolactone trifluoro methyl benzoate purity
Embodiment
Form by the following examples, Schizonepetolactone trifluoro methyl benzoate the present invention relates to and preparation method thereof is described in further detail, but this should be interpreted as to the scope of the above-mentioned theme of the present invention only limits to following example, all technology realizing based on foregoing of the present invention all belong to scope of the present invention.
Embodiment 1: take the Schizonepetolactone (method disclosing according to Chinese patent CN201010217622.1, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to obtain through oxidation preparation with the commercially available Herba Schizonepetae volatile oil of extraction by steam distillation gained, purity is more than 98%) 18.2mg (0.10mmol), to trifluoromethylbenzoic acid 47.5mg (0.25mmol, domestic AR level), DMAP 12.3mg (0.10mmol, domestic AR level), be placed in 50mL round-bottomed flask, add 4mL methylene dichloride (domestic AR level), stirring is dissolved it completely, add DCC 51.6mg (0.25mmol, domestic AR level), in room temperature (20-25 ℃), react, TLC checks reaction end.After reaction finishes, drip methyl alcohol (domestic AR level) and make solution clarification, add the about 500mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), underpressure distillation solvent is to dry.Take 5g silica gel dress post, eluent (sherwood oil (60-90 ℃, domestic AR level): ethyl acetate (domestic AR level)=5: 1) wash-out, during wash-out 40mL left and right, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, now collect elutriant, every 5mL collects once, during about 30mL left and right, TLC follows the tracks of and finds target compound wash-out substantially completely, merge elutriant, reclaim under reduced pressure elutriant, can obtain Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 83%.
Embodiment 2:
The Schizonepetolactone trifluoro methyl benzoate structure elucidation that embodiment 1 prepares:
HR-ESI-MS:m/z 355.2029[M+H]
+(calculated value C
18h
17f
3o
4for: 354.3204); [α]
20.5 d,+41.3 ° of (CH
3oH).
IR (KBr compressing tablet, cm
-1): 3063 (ν
Φ-H); 2931,2862 (saturated cyclic hydrocarbons ν
cH); 1697 (interior ester carbonyl group ν
c=O); 1655 (carbonyl ν
c=O); 1586,1537,1500,1437 (conjugation phenyl ring ν
c=C); 850,710 (phenyl ring para-orientation γ
Φ-H).
UV (CH
3oH) λ
max: 225.0nm, prompting compound has conjugation Absorption Characteristics.See accompanying drawing 1
1H?NMR(300MHz，CDCl
3，ppm)：δ1.07(d，3H，J＝6.6Hz，6’-CH
3)，1.13(dd，1H，J＝4.2，13.2Hz，5a-H)，1.32(m，1H，4a-H)，1.93(s，3H，3’-H)，1.96-2.07(m，2H，5b-H，6-H)，2.27(m，1H，4b-H)，2.80-2.94(m，2H，7-H)，7.62(t，1H，J＝7.8Hz，Ar-H)，7.86(d，1H，J＝7.8Hz，Ar-H)，8.19(d，1H，J＝7.8Hz，Ar-H)，8.24(s，1H，Ar-H)。
13C?NMR(75MHz，CDCl
3，ppm)：δ171.1(C-8)，163.1(C-7’)，162.5(C-3)，157.7(C-8’)，132.9(C-1’)，131.9，131.2(C-2’，C-6’)，129.9，128.8(C-3’，C-5’)，128.6(C-4’)，123.2(C-7)，104.5(C-4)，44.9(C-5)，34.5(C-1)，28.9(C6)，24.3(C-2)，20.9(C-10)，8.3(C-9)。
Schizonepetolactone trifluoro methyl benzoate purity: utilize HPLC method to detect, Schizonepetolactone trifluoro methyl benzoate peak area is 8078642, impurity total peak area is 247830, and adopting normalization method to calculate Schizonepetolactone trifluoro methyl benzoate purity is 97.0%.See accompanying drawing 2
Embodiment 3: take the Schizonepetolactone (method disclosing according to Chinese patent CN201010217622.1, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to obtain through oxidation preparation with the commercially available Herba Schizonepetae volatile oil of extraction by steam distillation gained, purity is more than 98%) 18.2mg (0.10mmol), to trifluoromethylbenzoic acid 47.5mg (0.25mmol, domestic AR level), DMAP 12.3mg (0.10mmol, domestic AR level), be placed in 50mL round-bottomed flask, add 4mL methylene dichloride (domestic AR level), stirring is dissolved it completely, add EDCI 46mg (0.24mmol, domestic AR level), in room temperature (20-25 ℃), react, TLC checks reaction end.After reaction finishes, drip methyl alcohol (domestic AR level) and make solution clarification, add the about 500mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), underpressure distillation solvent is to dry.Take 5g silica gel dress post, eluent (sherwood oil (60-90 ℃, domestic AR level): ethyl acetate (domestic AR level)=5: 1) wash-out, during wash-out 40mL left and right, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, now collect elutriant, every 5mL collects once, during about 30mL left and right, TLC follows the tracks of and finds target compound wash-out substantially completely, merge elutriant, reclaim under reduced pressure elutriant, can obtain Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 82%.
Embodiment 4: take the Schizonepetolactone (method disclosing according to Chinese patent CN201010217622.1, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to obtain through oxidation preparation with the commercially available Herba Schizonepetae volatile oil of extraction by steam distillation gained, purity is more than 98%) 24.3mg (0.15mmol), to trifluoromethylbenzoic acid 47.5mg 60.8mg (0.32mmol, domestic AR level), DMAP 18.5mg (0.15mmol, domestic AR level), be placed in 50mL round-bottomed flask, add 4mL methylene dichloride (domestic AR level), stirring is dissolved it completely, add DCC 66.1mg (0.32mmol, domestic AR level), in room temperature (20-25 ℃), react, TLC checks reaction end.After reaction finishes, drip methyl alcohol (domestic AR level) and make solution clarification, add the about 550mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), underpressure distillation solvent is to dry.Take 5g silica gel dress post, eluent (sherwood oil (60-90 ℃, domestic AR level): ethyl acetate (domestic AR level)=6: 1) wash-out, during wash-out 45mL left and right, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, now collect elutriant, every 5mL collects once, during about 35mL left and right, TLC follows the tracks of and finds target compound wash-out substantially completely, merge elutriant, reclaim under reduced pressure elutriant, can obtain Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 83%.
Embodiment 5: take the Schizonepetolactone (method disclosing according to Chinese patent CN201010217622.1, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to obtain through oxidation preparation with the commercially available Herba Schizonepetae volatile oil of extraction by steam distillation gained, purity is more than 98%) 24.3mg (0.15mmol), to trifluoromethylbenzoic acid 47.5mg 60.8mg (0.32mmol, domestic AR level), DMAP 18.5mg (0.15mmol, domestic AR level), be placed in 50mL round-bottomed flask, add 4mL methylene dichloride (domestic AR level), stirring is dissolved it completely, add EDCI 61.3mg (0.32mmol, domestic AR level), in room temperature (20-25 ℃), react, TLC checks reaction end.After reaction finishes, drip methyl alcohol (domestic AR level) and make solution clarification, add the about 550mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), underpressure distillation solvent is to dry.Take 5g silica gel dress post, eluent (sherwood oil (60-90 ℃, domestic AR level): ethyl acetate (domestic AR level)=6: 1) wash-out, during wash-out 45mL left and right, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, now collect elutriant, every 5mL collects once, during about 35mL left and right, TLC follows the tracks of and finds target compound wash-out substantially completely, merge elutriant, reclaim under reduced pressure elutriant, can obtain Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 81%.
Embodiment 6: take the Schizonepetolactone (method disclosing according to Chinese patent CN201010217622.1, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to obtain through oxidation preparation with the commercially available Herba Schizonepetae volatile oil of extraction by steam distillation gained, purity is more than 98%) 36.5mg (0.20mmol), to trifluoromethylbenzoic acid 72.2mg (0.38mmol, domestic AR level), DMAP 24.5mg (0.20mmol, domestic AR level), be placed in 50mL round-bottomed flask, add 5mL methylene dichloride (domestic AR level), stirring is dissolved it completely, add DCC 78.5mg (0.38mmol, domestic AR level), in room temperature (20-25 ℃), react, TLC checks reaction end.After reaction finishes, drip methyl alcohol (domestic AR level) and make solution clarification, add the about 600mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), underpressure distillation solvent is to dry.Take 6g silica gel dress post, eluent (sherwood oil (60-90 ℃, domestic AR level): ethyl acetate (domestic AR level)=7: 1) wash-out, during wash-out 50mL left and right, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, now collect elutriant, every 5mL collects once, during about 40mL left and right, TLC follows the tracks of and finds target compound wash-out substantially completely, merge elutriant, reclaim under reduced pressure elutriant, can obtain Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 84%.
Embodiment 7: take the Schizonepetolactone (method disclosing according to Chinese patent CN201010217622.1, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to obtain through oxidation preparation with the commercially available Herba Schizonepetae volatile oil of extraction by steam distillation gained, purity is more than 98%) 36.5mg (0.20mmol), to trifluoromethylbenzoic acid 72.2mg (0.38mmol, domestic AR level), DMAP 24.5mg (0.20mmol, domestic AR level), be placed in 50mL round-bottomed flask, add 5mL methylene dichloride (domestic AR level), stirring is dissolved it completely, add EDCI 72.8mg (0.38mmol, domestic AR level), in room temperature (20-25 ℃), react, TLC checks reaction end.After reaction finishes, drip methyl alcohol (domestic AR level) and make solution clarification, add the about 600mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), underpressure distillation solvent is to dry.Take 6g silica gel dress post, eluent (sherwood oil (60-90 ℃, domestic AR level): ethyl acetate (domestic AR level)=7: 1) wash-out, during wash-out 50mL left and right, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, now collect elutriant, every 5mL collects once, during about 40mL left and right, TLC follows the tracks of and finds target compound wash-out substantially completely, merge elutriant, reclaim under reduced pressure elutriant, can obtain Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 82%.
The anti-H3N2 virus function of embodiment 8 Schizonepetolactone trifluoro methyl benzoates
1 virus titer (TCID
50) mensuration
The preparation of 1.1 influenza viruses
Utilize chick embryo allantoic cavity inoculation method to prepare influenza virus, results allantoic fluid, by hemagglutination test (HA test), measure viral existence, after packing-70 ℃ frozen.
The dilution of 1.2 viruses
Get the frozen viral allantoic fluid of a pipe, dilution in 1: 10.
The virus liquid that the first round adds 146 μ L to dilute at 1: 10, then does serial log10 dilution, makes it to become 10
-1, 10
-2, 10
-3... 10
-10.100 μ L virus liquids are contained in every hole, and each extent of dilution is inoculated a tandem totally 8 holes.
The preparation of 1.3MDCK cell and the mensuration of virus titer
Use and mdck cell was gone down to posterity at 1: 10 in first 2 days, make it 70%-90% in blocks, discard cell culture fluid, with 5mL EDTA-pancreatin, wash cell once, then discard.4mL-5mL EDTA-pancreatin is covered to thin (162cm
2tissue Culture Flask) digest 10min～20min in 37 ℃ of incubators.When cell starts to come off, add 5mL～10mLMDCK cell culture fluid, piping and druming cell dispersion also proceeds to centrifuge tube by cell, and the centrifugal 5min of 2000r/min, with PBS washing 2 times, to remove bovine serum.Cell suspension, in 1mL viral dilution liquid, is is fully blown and beaten to cell dispersion with suction pipe, add viral dilution liquid to 10mL, by cell counting count board counting cells quantity.With viral dilution liquid, cell dilution is become to 1.5 * 10
5cell/mL, adds 100 μ L cells (1.5 * 10
4/ hole) in the good viral Microtitration plates of dilution.If two tandems are made in normal cell contrast, at 37 ℃, 5%CO
2in incubator, cultivate, observe 7 days and record result.
Press Reed-Muench Liang Shi method and calculate TCID
50.
2 sample cell toxicity tests
The preparation of 2.1 sample concentrations
By above-described embodiment 1 method, prepare sample, first with methyl-sulphoxide, be mixed with 20mg/mL.Then using mdck cell maintenance medium (cell culture fluid that does not contain serum) to dilute is respectively 200 μ g/mL, 100 μ g/mL, 50 μ g/mL, 25 μ g/mL, 12.5 μ g/mL, 6.25 μ g/mL, 3.125 μ g/mL, 1.562 μ g/mL.
2.2 toxotest
Mdck cell is 37 ℃ of 96 well culture plate monolayer culture, and 5%CO2 cultivates 24 hours, inhales and abandons supernatant liquor, adds respectively different concns liquid, 4 holes, and every hole adds liquid 100 μ L.Through 72 hours observation of cell forms, calculate medicine and cause cell half toxicity T C
50.
3 cytopathic effect inhibition tests
Mdck cell is at 37 ℃ of 96 well culture plate monolayer culture, 5%CO
2cultivate 24 hours, inhale and abandon supernatant liquor, cell washs through diluent, and every hole adds washings 100 μ L, inhales and abandons washings, adds 30TCID50 virus liquid, and 37 ℃, 5%CO
2adsorb 2 hours, suck virus, add liquid under maximal non-toxic concentration, 4 holes, every hole dosing 100 μ L.Through 37 ℃, 5%CO
2cultivate 72 hours, observe CPE (pathology), establish cell control group, virus control group, positive controls (ribavirin) and medicine group are observed CPE simultaneously, calculate IC50 (half effective inhibition concentration) and therapeutic index TI value.
4 results
Compound Schizonepetolactone trifluoro methyl benzoate shows good anti-H
3n
2activity, IC
50be 10.53 μ g/mL, TC
50be 26.7 μ g/mL, TI is 2.54.Under similarity condition, Schizonepetolactone does not show good anti-H
3n
2activity, therefore, Schizonepetolactone trifluoro methyl benzoate has the anti-H that is significantly better than Schizonepetolactone in vitro
3n
2active.In Table 1.
Table 1 Schizonepetolactone trifluoro methyl benzoate In Vitro Anti H
3n
2active
Note: "-" represents that sample is at TC
50concentration lower time has no maybe will not be detected viral inhibition.
TI＝TC
50/IC
50。
Claims (4)
1. Schizonepetolactone trifluoro methyl benzoate, has following structure:
2. a preparation method for Schizonepetolactone trifluoro methyl benzoate as claimed in claim 1, is characterized in that comprising the steps:
A. get Schizonepetolactone, appropriate to trifluoromethylbenzoic acid and DMAP, these three kinds of material amount of substance ratios are 0.5～1.5: 1.5～2.5: 0.5～1.5, be placed in reaction vessel, add methylene dichloride, stirring is dissolved it completely, adds N, N '-dicyclohexylcarbodiimide or 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride, these two kinds of material amount of substances are 1.5～2.5 times of Schizonepetolactone, in room temperature reaction, TLC checks reaction end, obtains reaction solution;
B. by A step gained reaction solution, drip methyl alcohol and make solution clarification, add silica gel, underpressure distillation solvent, to dry, obtains silica gel compound sample;
C. the silica obtained compound sample dress of B step post is carried out to column chromatography, with the petroleum ether-ethyl acetate that volume proportion is 4～7: 1, carry out wash-out, stream part that collection contains Schizonepetolactone trifluoro methyl benzoate, reclaim under reduced pressure elutriant after merging, can obtain Schizonepetolactone trifluoro methyl benzoate white crystalline powder.
3. the preparation method of Schizonepetolactone trifluoro methyl benzoate as claimed in claim 2, is characterized in that, Schizonepetolactone in steps A is 1: 2: 1 to trifluoromethylbenzoic acid and three kinds of material amount of substance ratios of DMAP; The N adding, N '-dicyclohexylcarbodiimide or 1-(3-dimethylamino-propyl)-3-ethyl-carbodiimide hydrochloride, these two kinds of material amount of substances are 2 times of Schizonepetolactone; The volume proportion of step C PetroChina Company Limited. ether-ethyl acetate is 5: 1.
4. the application of Schizonepetolactone trifluoro methyl benzoate as claimed in claim 1 in preparing anti-influenza virus medicament.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210523879.9A CN102942544B (en) | 2012-12-07 | 2012-12-07 | Nepetalactone trifluoromethyl benzoate as well as preparation process and use of nepetalactone trifluoromethyl benzoate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210523879.9A CN102942544B (en) | 2012-12-07 | 2012-12-07 | Nepetalactone trifluoromethyl benzoate as well as preparation process and use of nepetalactone trifluoromethyl benzoate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102942544A CN102942544A (en) | 2013-02-27 |
| CN102942544B true CN102942544B (en) | 2014-08-27 |
Family
ID=47725560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210523879.9A Active CN102942544B (en) | 2012-12-07 | 2012-12-07 | Nepetalactone trifluoromethyl benzoate as well as preparation process and use of nepetalactone trifluoromethyl benzoate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102942544B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107753478A (en) * | 2017-11-13 | 2018-03-06 | 贾红琴 | Application of the nepetalactone trifluoro methyl benzoate in Parkinson's are treated |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1323793A (en) * | 2001-04-09 | 2001-11-28 | 南京中医药大学 | Schizonepeta lactone and its extraction process and use |
| WO2003084946A1 (en) * | 2002-04-03 | 2003-10-16 | E.I. Du Pont De Nemours And Company | Production of dihydronepetalactone by hydrogenation of nepetalactone |
| US20100278889A1 (en) * | 2005-03-09 | 2010-11-04 | E. I. Du Pont De Nemours And Company | Compositions having sustained-release insect repellency |
| CN101885715A (en) * | 2010-07-06 | 2010-11-17 | 南京中医药大学 | Preparation method for nepetalactone |
-
2012
- 2012-12-07 CN CN201210523879.9A patent/CN102942544B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1323793A (en) * | 2001-04-09 | 2001-11-28 | 南京中医药大学 | Schizonepeta lactone and its extraction process and use |
| WO2003084946A1 (en) * | 2002-04-03 | 2003-10-16 | E.I. Du Pont De Nemours And Company | Production of dihydronepetalactone by hydrogenation of nepetalactone |
| US20100278889A1 (en) * | 2005-03-09 | 2010-11-04 | E. I. Du Pont De Nemours And Company | Compositions having sustained-release insect repellency |
| CN101885715A (en) * | 2010-07-06 | 2010-11-17 | 南京中医药大学 | Preparation method for nepetalactone |
Non-Patent Citations (4)
| Title |
|---|
| Oxidative substitution reactions of organostannyl compounds with lead tetraacetate A convenient route to 5-alkylidene-2(5H)-furanones;Yamamoto Makoto et al;《Bulletin of the Chemical Society of Japan》;19921231;第65卷(第9期);2366-2370 * |
| Yamamoto Makoto et al.Oxidative substitution reactions of organostannyl compounds with lead tetraacetate A convenient route to 5-alkylidene-2(5H)-furanones.《Bulletin of the Chemical Society of Japan》.1992,第65卷(第9期), |
| 裂叶荆芥芥穗黄酮及两张单萜成分研究;郭雪等;《东北师大学报自然科学版》;20021231;第34卷(第4期);45-49 * |
| 郭雪等.裂叶荆芥芥穗黄酮及两张单萜成分研究.《东北师大学报自然科学版》.2002,第34卷(第4期), |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102942544A (en) | 2013-02-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104744433B (en) | ALD and the purposes as EV71 virus with CAV16 viral inhibitors thereof | |
| CN114292272A (en) | Nucleoside compound and application thereof | |
| CN104922141A (en) | siRNA composition for treating viral hepatitis B | |
| CN101040915A (en) | Method for preparing a Shuanhuanglian injection and the component detecting method | |
| JP7123417B2 (en) | Anxiolytic deuterium compound and its medicinal use | |
| CN105175481A (en) | Highly-oxidized diterpenoid compound and preparation method and medical application thereof | |
| CN105503807A (en) | Catechin derivative named as epicatechin trans caffeic acid ester and preparation method and application thereof | |
| CN102964321B (en) | Nepetalactone fluorobenzoate, preparation technology and usage thereof | |
| CA2982200C (en) | Phillygenin glucuronic acid derivative as well as preparation method and application thereof | |
| CN102942544B (en) | Nepetalactone trifluoromethyl benzoate as well as preparation process and use of nepetalactone trifluoromethyl benzoate | |
| CN104628803B (en) | A kind of rape pollen alkali A and caper alkali D and the like total synthesis method | |
| CN105418545A (en) | Novel isocoumarin compound and preparation method and medical application thereof | |
| CN103012338B (en) | Nepeta lactone parabromobenzoate and preparation process and application thereof | |
| CN104945361B (en) | Germacrane Sesquiterpenoids derivative and preparation method and application | |
| CN103626812B (en) | Gloomy glycosides compound of a kind of new Bali and uses thereof in rhizoma Gastrodiae | |
| CN113149988B (en) | Preparation method and application of ganciclovir | |
| CN101774921A (en) | Method for preparing dicaffeoylquinic acid methyl compound and composition thereof | |
| CN111670191B (en) | Crystal form of pyridone derivative, preparation method and application | |
| CN102942545B (en) | Nepetalactone-o-bromobenzoic acid ester as well as preparation process and use of nepetalactone-o-bromobenzoic acid ester | |
| CN105949044A (en) | Imipramine hydrochloride pharmaceutical composition and medical application thereof | |
| CN105669816A (en) | Novel steroid compound, preparation method and medicinal application thereof | |
| CN103387580B (en) | Stemona alkaloids monomer component and uses thereof | |
| CN101856347B (en) | Extract of leontopodic acid plant and application of active ingredients thereof in treating hepatitis | |
| CN104814973B (en) | Application in the drug of diseases associated with inflammation of the Cappariloside A in preparation for treating influenza and influenza virus mediation | |
| CN102241682A (en) | Preparation method for fissistigine A |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |