CN102942544A - 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
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- CN102942544A CN102942544A CN2012105238799A CN201210523879A CN102942544A CN 102942544 A CN102942544 A CN 102942544A CN 2012105238799 A CN2012105238799 A CN 2012105238799A CN 201210523879 A CN201210523879 A CN 201210523879A CN 102942544 A CN102942544 A CN 102942544A
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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 by extracting a kind of Loliolide get in the Chinese medicinal materials schizonepeta,, be colourless grain crystalline substance (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, so that the preparation manipulation of Schizonepetolactone is simplified, yield improves, production cost reduces.But Schizonepetolactone external 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 the having sick active Schizonepetolactone derivative of stronger In Vitro Anti influenza.But up to now, not yet there is report behind trifluoro methyl benzoate, to obtain the Schizonepetolactone trifluoro methyl benzoate by Schizonepetolactone.
Summary of the invention
The object of the present invention is to provide and a kind ofly behind trifluoro methyl benzoate, obtain Schizonepetolactone trifluoro methyl benzoate and its preparation method and as the purposes of medicine by Schizonepetolactone.
Technical scheme of the present invention such 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, an amount of 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, place reaction vessel, add methylene dichloride, stirring is dissolved it fully, 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, gets reaction solution;
B. with A step gained reaction solution, drip methyl alcohol and make the solution clarification, add silica gel, the underpressure distillation solvent gets the silica gel compound sample to doing;
C. the silica obtained compound sample dress of B step post is carried out column chromatography, be that 4～7: 1 petroleum ether-ethyl acetate carries out wash-out with volume proportion, collection contains stream part of Schizonepetolactone trifluoro methyl benzoate, reclaim under reduced pressure elutriant after merging can get Schizonepetolactone trifluoro methyl benzoate white crystalline powder.
The preparation method of Schizonepetolactone trifluoro methyl benzoate among the above-mentioned steps A, Schizonepetolactone is 1: 2: 1 to trifluoromethylbenzoic acid and three kinds of material amount of substances of DMAP ratio; The N that adds, 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 preferably anti-H
3N
2Therefore activity 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, the preparation method is easy to be inexpensive, and has stronger physiologically active.
Description of drawings
The ultraviolet spectrogram of Fig. 1 compound Schizonepetolactone trifluoro methyl benzoate, λ max:225.0nm, the prompting compound has the 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, the Schizonepetolactone trifluoro methyl benzoate that the present invention relates to and preparation method thereof is described in further detail, but this should be interpreted as that the scope of the above-mentioned theme of the present invention only limits to following example, all technology that realizes based on foregoing of the present invention all belong to scope of the present invention.
Embodiment 1: take by weighing Schizonepetolactone (according to the method for Chinese patent CN201010217622.1 disclosure, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to get through the 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 the 50mL round-bottomed flask, add 4mL methylene dichloride (domestic AR level), stirring is dissolved it fully, add DCC 51.6mg (0.25mmol, domestic AR level), in room temperature (20-25 ℃) reaction, TLC checks reaction end.After the reaction end, drip methyl alcohol (domestic AR level) and make the solution clarification, add approximately 500mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), the underpressure distillation solvent is to doing.Take by weighing 5g silica gel dress post, eluent ((60-90 ℃ of sherwood oil, domestic AR level): ethyl acetate (domestic AR level)=5: 1) wash-out, during the wash-out 40mL left and right sides, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, collect elutriant this moment, every 5mL collects once, approximately TLC follows the tracks of and finds the substantially complete wash-out of target compound during the 30mL left and right sides, merge elutriant, the reclaim under reduced pressure elutriant can get 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, the prompting compound has the 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 the HPLC method to detect, Schizonepetolactone trifluoro methyl benzoate peak area is 8078642, the 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 by weighing Schizonepetolactone (according to the method for Chinese patent CN201010217622.1 disclosure, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to get through the 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 the 50mL round-bottomed flask, add 4mL methylene dichloride (domestic AR level), stirring is dissolved it fully, add EDCI 46mg (0.24mmol, domestic AR level), in room temperature (20-25 ℃) reaction, TLC checks reaction end.After the reaction end, drip methyl alcohol (domestic AR level) and make the solution clarification, add approximately 500mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), the underpressure distillation solvent is to doing.Take by weighing 5g silica gel dress post, eluent ((60-90 ℃ of sherwood oil, domestic AR level): ethyl acetate (domestic AR level)=5: 1) wash-out, during the wash-out 40mL left and right sides, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, collect elutriant this moment, every 5mL collects once, approximately TLC follows the tracks of and finds the substantially complete wash-out of target compound during the 30mL left and right sides, merge elutriant, the reclaim under reduced pressure elutriant can get Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 82%.
Embodiment 4: take by weighing Schizonepetolactone (according to the method for Chinese patent CN201010217622.1 disclosure, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to get through the 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 the 50mL round-bottomed flask, add 4mL methylene dichloride (domestic AR level), stirring is dissolved it fully, add DCC 66.1mg (0.32mmol, domestic AR level), in room temperature (20-25 ℃) reaction, TLC checks reaction end.After the reaction end, drip methyl alcohol (domestic AR level) and make the solution clarification, add approximately 550mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), the underpressure distillation solvent is to doing.Take by weighing 5g silica gel dress post, eluent ((60-90 ℃ of sherwood oil, domestic AR level): ethyl acetate (domestic AR level)=6: 1) wash-out, during the wash-out 45mL left and right sides, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, collect elutriant this moment, every 5mL collects once, approximately TLC follows the tracks of and finds the substantially complete wash-out of target compound during the 35mL left and right sides, merge elutriant, the reclaim under reduced pressure elutriant can get Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 83%.
Embodiment 5: take by weighing Schizonepetolactone (according to the method for Chinese patent CN201010217622.1 disclosure, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to get through the 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 the 50mL round-bottomed flask, add 4mL methylene dichloride (domestic AR level), stirring is dissolved it fully, add EDCI 61.3mg (0.32mmol, domestic AR level), in room temperature (20-25 ℃) reaction, TLC checks reaction end.After the reaction end, drip methyl alcohol (domestic AR level) and make the solution clarification, add approximately 550mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), the underpressure distillation solvent is to doing.Take by weighing 5g silica gel dress post, eluent ((60-90 ℃ of sherwood oil, domestic AR level): ethyl acetate (domestic AR level)=6: 1) wash-out, during the wash-out 45mL left and right sides, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, collect elutriant this moment, every 5mL collects once, approximately TLC follows the tracks of and finds the substantially complete wash-out of target compound during the 35mL left and right sides, merge elutriant, the reclaim under reduced pressure elutriant can get Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 81%.
Embodiment 6: take by weighing Schizonepetolactone (according to the method for Chinese patent CN201010217622.1 disclosure, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to get through the 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 the 50mL round-bottomed flask, add 5mL methylene dichloride (domestic AR level), stirring is dissolved it fully, add DCC 78.5mg (0.38mmol, domestic AR level), in room temperature (20-25 ℃) reaction, TLC checks reaction end.After the reaction end, drip methyl alcohol (domestic AR level) and make the solution clarification, add approximately 600mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), the underpressure distillation solvent is to doing.Take by weighing 6g silica gel dress post, eluent ((60-90 ℃ of sherwood oil, domestic AR level): ethyl acetate (domestic AR level)=7: 1) wash-out, during the wash-out 50mL left and right sides, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, collect elutriant this moment, every 5mL collects once, approximately TLC follows the tracks of and finds the substantially complete wash-out of target compound during the 40mL left and right sides, merge elutriant, the reclaim under reduced pressure elutriant can get Schizonepetolactone trifluoro methyl benzoate white crystalline powder, purity is more than 97%, yield 84%.
Embodiment 7: take by weighing Schizonepetolactone (according to the method for Chinese patent CN201010217622.1 disclosure, adopt labiate schizonepeta Schizonepeta tenuifolia Briq. flower fringe to get through the 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 the 50mL round-bottomed flask, add 5mL methylene dichloride (domestic AR level), stirring is dissolved it fully, add EDCI 72.8mg (0.38mmol, domestic AR level), in room temperature (20-25 ℃) reaction, TLC checks reaction end.After the reaction end, drip methyl alcohol (domestic AR level) and make the solution clarification, add approximately 600mg of triplication silica gel (Haiyang Chemical Plant, Qingdao produces, and column chromatography is used), the underpressure distillation solvent is to doing.Take by weighing 6g silica gel dress post, eluent ((60-90 ℃ of sherwood oil, domestic AR level): ethyl acetate (domestic AR level)=7: 1) wash-out, during the wash-out 50mL left and right sides, TLC follows the tracks of can find target compound Schizonepetolactone trifluoro methyl benzoate, collect elutriant this moment, every 5mL collects once, approximately TLC follows the tracks of and finds the substantially complete wash-out of target compound during the 40mL left and right sides, merge elutriant, the reclaim under reduced pressure elutriant can get 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
1.1 the preparation of influenza virus
Utilize the chick embryo allantoic cavity inoculation method to prepare influenza virus, the results allantoic fluid is measured the existence of virus by hemagglutination test (HA test), after the packing-70 ℃ frozen.
1.2 the dilution of virus
Get the frozen viral allantoic fluid of a pipe, dilution in 1: 10.
The first round adds the virus liquid that 146 μ L diluted at 1: 10, then does serial log10 dilution, makes it to become 10
-1, 10
-2, 10
-3... 10
-10100 μ L virus liquids are contained in every hole, and each extent of dilution is inoculated a tandem totally 8 holes.
1.3MDCK the preparation of cell and the mensuration of virus titer
Use and mdck cell gone down to posterity at 1: 10 in front 2 days, make it 70%-90% in blocks, discard cell culture fluid, wash cell once with 5mL EDTA-pancreatin, then discard.4mL-5mL EDTA-pancreatin is covered thin (162cm
2Tissue Culture Flask) digest 10min～20min in 37 ℃ of incubators.When treating that cell begins to come off, add 5mL～10mLMDCK cell culture fluid, blow and beat cell dispersion and change cell over to centrifuge tube, the centrifugal 5min of 2000r/min is with PBS washing 2 times, to remove bovine serum.Cell suspension in 1mL viral dilution liquid, is is fully blown and beaten cell dispersion with suction pipe, add viral dilution liquid to 10mL, with cell counting count board counting cells quantity.With viral dilution liquid cell dilution is become 1.5 * 10
5Cell/mL adds 100 μ L cells (1.5 * 10
4/ hole) in the Microtitration plates of the good virus of dilution.If two tandems are made in the normal cell contrast, at 37 ℃, 5%CO
2Cultivate in the incubator, observed 7 days and record the result.
Press Reed-Muench Liang Shi method and calculate TCID
50
2 sample cell toxicity tests
2.1 the preparation of sample concentration
Prepare sample by above-described embodiment 1 method, at first be mixed with 20mg/mL with methyl-sulphoxide.Then using mdck cell maintenance medium (cell culture fluid that does not namely contain serum) to dilute respectively is 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 cultivated 24 hours, inhales and abandons supernatant liquor, adds respectively the different concns liquid, and 4 holes, every hole add liquid 100 μ L.Through 72 hours observation of cell forms, calculate medicine and cause cell half toxicity T C
50
The test of 3 cytopathic effect inhibitions
Mdck cell is at 37 ℃ of 96 well culture plate monolayer culture, 5%CO
2Cultivated 24 hours, and inhaled and abandon supernatant liquor, cell washs through diluent, and every hole adds washings 100 μ L, inhales and abandons washings, adds the 30TCID50 virus liquid, and 37 ℃, 5%CO
2Adsorbed 2 hours, and sucked virus, add liquid under the maximal non-toxic concentration, 4 holes, every hole dosing 100 μ L.Through 37 ℃, 5%CO
2Cultivated 72 hours, and observed CPE (pathology), establish the cell control group, the 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 preferably anti-H
3N
2Activity, IC
50Be 10.53 μ g/mL, TC
50Be 26.7 μ g/mL, TI is 2.54.Under the similarity condition, Schizonepetolactone does not show preferably anti-H
3N
2Activity, therefore, the Schizonepetolactone trifluoro methyl benzoate has an anti-H that significantly is better than Schizonepetolactone external
3N
2Active.See Table 1.
Table 1 Schizonepetolactone trifluoro methyl benzoate In Vitro Anti H
3N
2Active
Annotate: "-" expression sample is at TC
50The inhibition that concentration lower time has no virus maybe will not detect.
TI＝TC
50/IC
50。
Claims (4)
1. Schizonepetolactone trifluoro methyl benzoate has following structure:
2. the preparation method of a Schizonepetolactone trifluoro methyl benzoate as claimed in claim 1 is characterized in that comprising the steps:
A. get Schizonepetolactone, an amount of 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, place reaction vessel, add methylene dichloride, stirring is dissolved it fully, 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, gets reaction solution;
B. with A step gained reaction solution, drip methyl alcohol and make the solution clarification, add silica gel, the underpressure distillation solvent gets the silica gel compound sample to doing;
C. the silica obtained compound sample dress of B step post is carried out column chromatography, be that 4～7: 1 petroleum ether-ethyl acetate carries out wash-out with volume proportion, collection contains stream part of Schizonepetolactone trifluoro methyl benzoate, reclaim under reduced pressure elutriant after merging can get 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 the steps A is 1: 2: 1 to trifluoromethylbenzoic acid and three kinds of material amount of substances of DMAP ratio; The N that adds, 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 the preparation anti-influenza virus medicament.
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