CN102382073A - Rupestonic acid isoxazole amides derivative, preparation method and application thereof - Google Patents
Rupestonic acid isoxazole amides derivative, preparation method and application thereof Download PDFInfo
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- CN102382073A CN102382073A CN2011102134990A CN201110213499A CN102382073A CN 102382073 A CN102382073 A CN 102382073A CN 2011102134990 A CN2011102134990 A CN 2011102134990A CN 201110213499 A CN201110213499 A CN 201110213499A CN 102382073 A CN102382073 A CN 102382073A
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- rupestonic acid
- isoxazole
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Abstract
The invention relates to a rupestonic acid isoxazole amides derivative, a preparation method and application thereof, wherein the derivative takes rupestonic acid and 3-substituted phenyl-5-aminomethyl-isoxazole derivative as raw materials, and is synthesized under the action of a condensing agent N, N-dicyclohexyl carbon imidodicarbonic diamide, and invitro anti-influenza A virus (H3N2, H1N1) and influenza B virus activity tests are preliminarily carried out on the synthesized derivative. The experimental result shows that: the compound 2c (N-[(3-fluoro phenyl-isoxazole-5-yl)-methyl] -rupestonic acid amide) can restrain the activity of the influenza A virus H3H2 to a certain extent; and the compounds 2c (N-[(3-fluoro phenyl-isoxazole-5-yl)-methyl]-rupestonic acid amide) and 2e(N-[(3-methoxy phenyl-isoxazole-5-yl)-methyl]-rupestonic acid amide) can restrain the influenza B virus to a certain extent. The method has mild reaction conditions and simple and direct experimental steps.
Description
Technical field
The present invention relates to from dimension medicine Herba Achilleae, separate the monomeric compound rupestonic acid that obtains and be a series of rupestonic acid cycliton of parent compound institute synthetic analog derivative with it, compound has the pharmaceutical use of anti-first, Influenza B virus infection to this analog derivative through active test section.
Background technology
Feverfew Artemisia rupestris L. (Artemisia rupestris L.) in Xinjiang medication among the people with a long history, have anti-inflammatory, antianaphylaxis, antibiotic, anticancer, strengthening immunity, antidote against snake bite, protect the liver, anti-oxidant isoreactivity.At present the research major side of Artemisia rupestris L. is overweighted the evaluation of its chemical ingredients, and have several kinds to be that the compound medicine of staple goes on the market with the Herba Achilleae.Be the representative compound medicine that has gone on the market below:
Nomenclature of drug: compound Artemisia rupestris particle;
Manufacturing enterprise: the Western Regions, Xinjiang pharmaceutcal corporation, Ltd authentication code: the accurate word Z20026711 of traditional Chinese medicines;
Composition: Herba Achilleae, Leaf of Indigowoad, Root of Indigowoad;
Purposes: resolving toxin and disinhibiting the throat is used for flu, fever, swelling and pain in the throat.
Rupestonic acid (Rupestonic acid) is isolated a kind of multi-functional sesquiterpenoids that contains from Artemisia rupestris L.; Take the lead in this monomeric compound has been carried out preliminary anti-first, Influenza B virus and simple I, II type simplexvirus activity research, it is active that the result shows that this parent compound has certain inhibition to Influenza B virus.
The substituted isoxazoles heterocycle is one type and has extensive bioactive molecular structure, introduces the isoxazole heterocycle in the drug molecule, can change the character of drug molecule and receptors bind.
The present invention is incorporated into substituted isoxazole heterocycle in the rupestonic acid molecule, has synthesized a series of rupestonic acid cycliton analog derivatives, and reaction conditions is gentle, and experimental procedure is simple and direct.
Summary of the invention
The objective of the invention is to, a kind of rupestonic acid cycliton analog derivative is provided, this analog derivative is a raw material with rupestonic acid and 3-substituted-phenyl-5-aminomethyl-isoxazole, under the effect of condensing agent, be synthesized into.This method reaction conditions is gentle, and experimental procedure is simple and direct.Rupestonic acid cycliton analog derivative of the present invention is as the purposes of the medicine of anti-first type of preparation or Influenza B virus.
A kind of rupestonic acid cycliton analog derivative of the present invention, its structure such as general formula (I):
Wherein R be hydrogen (H), to chlorine (p-Cl), to fluorine (p-F), to methoxyl group (p-CH
3O), O-methoxy (o-CH
3O) or to methyl (p-CH
3).
The preparation method of described rupestonic acid cycliton analog derivative follows these steps to carry out:
A, with rupestonic acid and N, N-dicyclohexyl carbon imide is dissolved in the exsiccant THF, stirring reaction 10min under the ice bath;
B, 1-hydroxy benzo triazole and 4-Dimethylamino pyridine are dissolved in the exsiccant THF, are added drop-wise in the step a system, ice bath stirs 30min;
C, again 3-(substituted-phenyl)-5-aminomethyl isoxazole is added in the step b reaction system; After continuing ice bath stirring 30min, rise to room temperature naturally and continue reaction, after the TLC detection reaction is complete; The vacuum desolventizing; Residue is adopted the column chromatography gradient elution, and eluent is sherwood oil and ETHYLE ACETATE, promptly gets title product.
The volume ratio of eluent described in the step c is a sherwood oil: ETHYLE ACETATE=5: 1-2: 1.
The purposes of said rupestonic acid cycliton analog derivative in the medicine of anti-first type of preparation or Influenza B virus.
Rupestonic acid cycliton analog derivative of the present invention is that substituted isoxazole ring is incorporated in the rupestonic acid molecule, synthetic a series of rupestonic acid cycliton analog derivatives, and reaction formula is:
Wherein R is 2a:H (hydrogen), 2b:p-Cl (to chlorine), 2c:p-F (to fluorine), 2d:p-CH
3O (to methoxyl group), 2e:o-CH
3O (O-methoxy) or 2f:p-CH
3(to methyl).Institute's synthetic verivate has been carried out preliminary external anti-first type (H3N2; H1N1) and the Influenza B virus active testing; Experimental result shows that compound 2c (N-[(3-is to fluorophenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides) shows certain inhibition activity to first type H3N2 influenza virus; Compound 2c (N-[(3-is to fluorophenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides) and 2e (N-[(3-o-methoxyphenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides) show certain inhibition activity to Influenza B virus.
Embodiment
According to embodiment the present invention is further specified, but the present invention is not limited only to these embodiment.Reagent:
Rupestonic acid separates by ordinary method, purity: 98%, and HPLC detects, and remaining reagent is commercially available analytical pure.
The preparation of embodiment 1:N-[(3-phenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides
A, with 0.05g (0.20mmol) rupestonic acid and 0.05g (0.22mmol) N, N-dicyclohexyl carbon imide is dissolved in the 8mL exsiccant THF, stirring reaction 10min under the ice bath;
B, 0.04g (0.30mmol) 1-hydroxy benzo triazole and 0.03g (0.22mmol) 4-Dimethylamino pyridine are dissolved in the 3mL exsiccant THF, are added drop-wise in the step a system, ice bath stirs 30min;
C, again 0.05g (0.30mmol) 3-phenyl-5-aminomethyl-isoxazoles is added in the step b reaction system; After ice bath stirs 30min; Naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing; It is the volume ratio sherwood oil that residue is adopted the agent of column chromatography gradient elution: ETHYLE ACETATE=5: 1-2: 1 wash-out can obtain N-[(3-phenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides.
The preparation of embodiment 2:N-[(3-rubigan-isoxazole-5-bases)-methyl]-rupestonic acid acid amides
A, with 0.05g (0.20mmol) rupestonic acid and 0.05g (0.22mmol) N, N-dicyclohexyl carbon imide is dissolved in the 8mL exsiccant THF, stirring reaction 10min under the ice bath;
B, 0.04g (0.30mmol) 1-hydroxy benzo triazole and 0.03g (0.22mmol) 4-Dimethylamino pyridine are dissolved in the 3mL exsiccant THF, are added drop-wise in the step a system, ice bath stirs 30min;
C, again 0.06g (0.30mmol) 3-rubigan-5-aminomethyl-isoxazoles is added in the step b reaction system; After ice bath stirs 30min; Naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing; It is the volume ratio sherwood oil that residue is adopted the agent of column chromatography gradient elution: ETHYLE ACETATE=5: 1-2: 1 wash-out can obtain N-[(3-rubigan-isoxazole-5-bases)-methyl]-rupestonic acid acid amides.
The preparation of embodiment 3:N-[(3-is to fluorophenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides
A, with 0.05g (0.20mmol) rupestonic acid and 0.05g (0.22mmol) N, N-dicyclohexyl carbon imide is dissolved in the 8mL exsiccant THF, stirring reaction 10min under the ice bath;
B, 0.04g (0.30mmol) 1-hydroxy benzo triazole and 0.03g (0.22mmol) 4-Dimethylamino pyridine are dissolved in the 3mL exsiccant THF, are added drop-wise in the step a system, ice bath stirs 30min;
C, again 0.06g (0.30mmol) 3-is added in the step b reaction system fluorophenyl-5-aminomethyl-isoxazoles; After ice bath stirs 30min; Naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing; It is the volume ratio sherwood oil that residue is adopted the agent of column chromatography gradient elution: ETHYLE ACETATE=5: 1-2: 1 wash-out can obtain N-[(3-is to fluorophenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides.
The preparation of embodiment 4:N-[(3-p-methoxyphenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides
A, with 0.05g (0.20mmol) rupestonic acid and 0.05g (0.22mmol) N, N-dicyclohexyl carbon imide is dissolved in the 8mL exsiccant THF, stirring reaction 10min under the ice bath;
B, 0.04g (0.30mmol) 1-hydroxy benzo triazole and 0.03g (0.22mmol) 4-Dimethylamino pyridine are dissolved in the 3mL exsiccant THF, are added drop-wise in the step a system, after ice bath stirs 30min;
C, again 0.06g (0.30mmol) 3-p-methoxyphenyl-5-aminomethyl-isoxazoles is added in the step b reaction system; After ice bath stirs 30min; Naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing; It is the volume ratio sherwood oil that residue is adopted the agent of column chromatography gradient elution: ETHYLE ACETATE=5: 1-2: 1 wash-out can obtain N-[(3-p-methoxyphenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides.
The preparation of embodiment 5:N-[(3-o-methoxyphenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides
A, with 0.05g (0.20mmol) rupestonic acid and 0.05g (0.22mmol) N, N-dicyclohexyl carbon imide is dissolved in the 8mL exsiccant THF, stirring reaction 10min under the ice bath;
B, 0.04g (0.30mmol) 1-hydroxy benzo triazole and 0.03g (0.22mmol) 4-Dimethylamino pyridine are dissolved in the 3mL exsiccant THF, are added drop-wise in the step a system, ice bath stirs 30min;
C, again 0.06g (0.30mmol) 3-o-methoxyphenyl-5-aminomethyl-isoxazoles is added in the step b reaction system; After ice bath stirs 30min; Naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing; It is the volume ratio sherwood oil that residue is adopted the agent of column chromatography gradient elution: ETHYLE ACETATE=5: 1-2: 1 wash-out can obtain N-[(3-o-methoxyphenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides.
The preparation of embodiment 6:N-[(3-p-methylphenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides
A, with 0.05g (0.20mmol) rupestonic acid and 0.05g (0.22mmol) N, N-dicyclohexyl carbon imide is dissolved in the 8mL exsiccant THF, stirring reaction 10min under the ice bath;
B, 0.04g (0.30mmol) 1-hydroxy benzo triazole and 0.03g (0.22mmol) 4-Dimethylamino pyridine are dissolved in the 3mL exsiccant THF, are added drop-wise in the step a system, ice bath stirs 30min;
C, again 0.06g (0.30mmol) 3-p-methylphenyl-5-aminomethyl-isoxazoles is added in the step b reaction system; After ice bath stirs 30min; Naturally rise to room temperature and continue reaction, after the TLC detection reaction is complete, the vacuum desolventizing; It is the volume ratio sherwood oil that residue is adopted the agent of column chromatography gradient elution: ETHYLE ACETATE=5: 1-2: 1 wash-out can obtain N-[(3-p-methylphenyl-isoxazole-5-bases)-methyl]-rupestonic acid acid amides.
Embodiment 7
The present invention has carried out preliminary external anti-influenza virus activity test with the synthetic rupestonic acid cycliton analog derivative 2a-2f of institute, and the biological activity of antagonism first, Influenza B virus is measured:
Test philosophy: with MDCK (dog kidney) cell is the virus host cell, and working sample suppresses virus and causes cytopathy degree (CPE).
The material of test:
(1) virus strain: influenza A virus [312-2006 (H3N2), 219-2006 (H1N1)], Influenza B virus (the anti-97-13 of Ji) is cultivated in chick embryo allantoic cavity and go down to posterity temperature-80 ℃ preservation in September, 2006.
(2) sample preparation: sample is dissolved in methyl-sulphoxide, is made into suitable starting point concentration with nutrient solution again, does 3 times of dilutions with nutrient solution, each 8 extent of dilution.
(3) positive control drug: virazole, health abundant pharmaceutcal corporation, Ltd in Zhejiang produces (lot number 20050612).
Method:
(1) preparation of specimen solution
Each sample is dissolved in an amount of DMSO, is mixed with the starting point concentration of 1000 μ g/mL again with nutrient solution, take turns doing 3 times of dilutions with nutrient solution then, each 8 extent of dilution (concentration is followed successively by 250,62.5,15.6,3.9,1.0,0.2,0.06,0.02 μ g/mL).
(2) anti-influenza virus activity test
MDCK is inoculated in 96 well culture plates, places 5%CO
2, temperature was cultivated 24 hours for 37 ℃, and MDCK adds influenza first C-type virus C 10 respectively
-3(316 times of TCID
50), influenza B virus (Ji anti-97-13) 1/2 10
-2(158 times of TCID
50), 37 ℃ of absorption of temperature were shifted out viral liquid after 2 hours, added different dilution medicines respectively.If virus control and cell contrast, 37 ℃ of cultivations of temperature are treated virus control group lesion degree (CPE) and are observed the cytopathy degree (CPE) of respectively organizing (about 36 hours) when reaching 4+, calculate the susceptible malicious half-inhibition concentration (IC of each sample convection current
50) value.The active result of rupestonic acid cycliton analog derivative 2a-2f is shown in table 1, table 2:
The activity data of table 1 alpine yarrow herb ketoacid derivatives 2a-2f anti-influenza A virus (H3N2, H1N1)
The activity data of the anti-Influenza B virus of table 2 rupestonic acid cycliton analog derivative 2a-2f
TC
50: the poisonous concentration of half.
-: sample does not have the resisiting influenza virus activity when maximal non-toxic is measured.
SI: selectivity index.
SI＝TC
50/IC
50。
1 parent compound (rupestonic acid).
Claims (4)
1. rupestonic acid cycliton analog derivative is characterized in that the structure such as the general formula (I) of this verivate:
Wherein R be hydrogen, to chlorine, to fluorine, to methoxyl group, O-methoxy or to methyl.
2. the preparation method of rupestonic acid cycliton analog derivative according to claim 1 is characterized in that following these steps to carrying out:
A, with rupestonic acid and N, N-dicyclohexyl carbon imide is dissolved in the exsiccant THF, stirring reaction 10min under the ice bath;
B, 1-hydroxy benzo triazole and 4-Dimethylamino pyridine are dissolved in the exsiccant THF, are added drop-wise in the step a system, ice bath stirs 30min;
C, again 3-(substituted-phenyl)-5-aminomethyl isoxazole is added in the step b reaction system; After continuing ice bath stirring 30min, rise to room temperature naturally and continue reaction, after the TLC detection reaction is complete; The vacuum desolventizing; Residue is adopted the column chromatography gradient elution, and eluent is sherwood oil and ETHYLE ACETATE, promptly gets title product.
3. according to the said method of claim 2, it is characterized in that eluent volume ratio described in the step c is a sherwood oil: ETHYLE ACETATE=5: 1-2: 1.
4. the purposes of rupestonic acid cycliton analog derivative according to claim 1 in the medicine of preparation anti-influenza A virus.
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Cited By (3)
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| CN103058941A (en) * | 2013-01-31 | 2013-04-24 | 中国科学院新疆理化技术研究所 | Rupestonic acid containing heterocyclic ester derivatives and preparation method and use thereof |
| CN112961114A (en) * | 2021-02-20 | 2021-06-15 | 中国科学院新疆理化技术研究所 | 2-substituted rupestonic acid isoxazole amide derivative and preparation method and application thereof |
| CN116102518A (en) * | 2023-01-06 | 2023-05-12 | 喀什大学 | Synthesis method and application of rupestonic acid fluorescent probe |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103058941A (en) * | 2013-01-31 | 2013-04-24 | 中国科学院新疆理化技术研究所 | Rupestonic acid containing heterocyclic ester derivatives and preparation method and use thereof |
| CN112961114A (en) * | 2021-02-20 | 2021-06-15 | 中国科学院新疆理化技术研究所 | 2-substituted rupestonic acid isoxazole amide derivative and preparation method and application thereof |
| CN112961114B (en) * | 2021-02-20 | 2023-06-09 | 中国科学院新疆理化技术研究所 | 2-substituted rupestonic acid isoxazolamide derivative and preparation method and application thereof |
| CN116102518A (en) * | 2023-01-06 | 2023-05-12 | 喀什大学 | Synthesis method and application of rupestonic acid fluorescent probe |
| CN116102518B (en) * | 2023-01-06 | 2024-03-15 | 喀什大学 | Synthesis method and application of rupestonic acid fluorescent probe |
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