CN104892538A - Isolongifolene alkyl oxazolone as well as synthesis method and application thereof - Google Patents
Isolongifolene alkyl oxazolone as well as synthesis method and application thereof Download PDFInfo
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- CN104892538A CN104892538A CN201510334753.0A CN201510334753A CN104892538A CN 104892538 A CN104892538 A CN 104892538A CN 201510334753 A CN201510334753 A CN 201510334753A CN 104892538 A CN104892538 A CN 104892538A
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- Prior art keywords
- isolonglifolane
- oxazolones
- isolongifolene
- oxazolone
- alkyl
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- 0 CC(C)(C(CC1)CC11C(C)(C)C2)C1=CC2C1C(C*C*=C(C2=C=C)OCC2=O)C1 Chemical compound CC(C)(C(CC1)CC11C(C)(C)C2)C1=CC2C1C(C*C*=C(C2=C=C)OCC2=O)C1 0.000 description 2
- VCOCESNMLNDPLX-UHFFFAOYSA-N CC(C)(C(CC1)CC11C(C)(C)CC2)C1C2=O Chemical compound CC(C)(C(CC1)CC11C(C)(C)CC2)C1C2=O VCOCESNMLNDPLX-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses isolongifolene alkyl oxazolone as well as a synthesis method and an application thereof. The molecular formula of the isolongifolene alkyl oxazolone is C18H27N302, the molecular weight is 317.21, the physical state of the isolongifolene alkyl oxazolone is a white solid, and m.p. is 202 DEG C. The synthesis method comprises steps as follows: isolongifolanone is taken as a raw material and subjected to condensation through semicarbazide hydrochloride, and then semicarbazone is obtained; then the isolongifolene alkyl oxazolone is obtained through ring formation under the condition of reflux of absolute ethyl alcohol. The isolongifolene alkyl oxazolone shows good activity on inflammation elimination of cells and is a potential anti-inflammatory compound.
Description
Technical field
The present invention relates to organic compound synthesis technical field, be specifically related to isolonglifolane oxazolones and synthetic method thereof and application.
Background technology
Thiazole compound is the heterocyclic chemistry material of important five yuan that a class contains nitrogen and sulphur, due to containing abundant electronics, easily forms metal ion key, hydrogen bond and π-π, electrostatic and hydrophobic interaction.At field of medicaments, thiazole compound can be used as medicine and demonstrates huge research and development and be worth, and shows out huge DEVELOPMENT PROSPECT in anti-tumor disease, antimycotic disease, anticancer, anti-inflammatory analgesic, resistant to viral disease, parasiticide, the direction such as anti-oxidant.
Thiazolone is because having special biological activity and strong coordination ability, and having bactericidal, antitumor, many pharmaceutical activitys such as anti-inflammatory analgetic, spasmolytic, antidepressant, is in Artemisinin, found natural thiazolone compounds the earliest.Thiazolone structure is incorporated in compound molecule, probably due to addition, produces stronger biological activity, and then provide lead compound for drug screening.
Thiazolidone is considered to one and has bioactive bracket important compound, and thiazolidone part is successfully introduced ralitoline and can be used as a kind of effective anticonvulsion medicament, W-2900A is as hypertension medicine, and pioglitazone can be used as Hypoylycemic agents.This biological respinse curve diversity has attracted numerous investigator to note, explores this skeleton and has very large potentiality to be exploited.Deepika Gautam etc. use Mono Chloro Acetic Acid ion solvent thiosemicarbazone and benzofuranone to be reacted, obtained novel 4-thiazolidone after reacting with N-methyl toluene sulfonic acid.Equimolar amount thiosemicarbazone derivative and obtained 2, the 4-disubstituted thiazole of benzoyl bromide compound reaction, have studied suitable reaction scheme.Mar í a E.Caputto adopts microwave irradiation to use comparatively simple procedure, and synthesized series of new 4-aryl thiazole hydrazone (TZHs) by 1-indone, yield is (66-92%), and carries out spectral characterization to its product.Study these compounds active to parasite, cone whip body and the trypanosome of amastigote shape In Vitro Anti.Using the chemotherapeutics Rochagan used at present as selectivity with reference to agent, TZHs shows very outstanding activity.The compound analysis result of incubating from parasite free sterol shows, these novel TZHs effects may be suppress ergosterol biosynthesizing.The people such as Mogedda E Haiba describe the difference five or six-ring hydrogenated naphthalene derivative that a series of nitrogenous, oxygen and thia ring, S-glycosides or N-glucosides mix or condense.Use X-ray to characterize compound, evaluate new synthetic compound anti-cell toxic activity, have evaluated the inhibition of the breast cancer cell line In Vitro Anti cell proliferation of cultivating people.Research finds that chalcone derivative and the similar thing of they cyclisation mercaptopyrimidines can effectively suppress Zorubicin breast cancer cell to generate.The people such as Abhishek Kumar Jain point out that thiazolidone has a kind of important biomolecule active scaffold in bioactive compounds, and prove that thiazolidomycin active part is thiazolidone, it has fine resistance to streptomycete species.Be intended to the multiple biological activity of report thiazolinone derivative, filtered out simultaneously and had active compound, wherein some active compound is by the preclinical test stage.
Summary of the invention
Goal of the invention: for the deficiencies in the prior art, the object of the present invention is to provide isolonglifolane oxazolones, can meet anti-inflammatory and antitumor demand; Another object of the present invention is to the synthetic method that above-claimed cpd is provided.The present invention also has an object to be to provide the application of above-claimed cpd.
Technical scheme: in order to realize foregoing invention object, the technical solution used in the present invention is:
Isolonglifolane oxazolones, structural formula is
molecular formula is C
18h
27n
3o
2, molecular weight is 317.21, and states of matter is white solid, and m.p. is 202 DEG C.
The synthetic method of described isolonglifolane oxazolones, comprises the following steps:
1) under an acidic catalyst effect, isolongifanone and semicarbazide hydrochloride in organic solvent, react under reflux temperature, obtain semicarbazone;
2) under an acidic catalyst effect, semicarbazone and halogenated acetic acids ethyl ester, in organic solvent, react 8 ~ 12h under reflux temperature, obtain isolonglifolane oxazolones.
The synthetic method of described isolonglifolane oxazolones, comprises below step:
1) in the there-necked flask being furnished with agitator and thermometer, add dehydrated alcohol successively, isolongifanone, semicarbazide hydrochloride, the vitriol oil, heating reflux reaction 12-24h, obtains semicarbazone;
2) in the there-necked flask being furnished with agitator and thermometer, add dehydrated alcohol successively, semicarbazone, halogenated acetic acids ethyl ester, an acidic catalyst, be heated to reflux temperature reaction 8-12h, obtain isolonglifolane oxazolones.
Described an acidic catalyst is sodium acetate.
Described halogenated acetic acids ethyl ester is ethyl bromoacetate.
Described isolonglifolane oxazolones is preparing the application in anti-inflammatory drug.
Beneficial effect: compared with prior art, advantage of the present invention is:
1) adopt the isolongifanone in natural extract turps the abundantest to be raw material, synthesizing new thiazolone compounds, provides a kind of novel method of synthesizing isolonglifolane base thiazolone compounds.
2) isolonglifolane base thiazolone compounds is provided to the restraining effect of Human umbilical vein endothelial cells (HUVECs) Inflammatory response.
3) for designing the analysis of novel azaheterocyclic compound and structure activity relationship, certain reference value is provided, significant to the terebinthine field that utilizes of expansion China.
Embodiment
The present invention is illustrated further below in conjunction with specific embodiment.
Embodiment 1
The synthetic method of isolonglifolane oxazolones, step is as follows:
1) isolongifanone and semicarbazide hydrochloride carry out condensation substitution reaction and generate semicarbazone.
Concrete operations are: being furnished with in magnetic stirring apparatus, thermometer and reflux condensing tube 50mL there-necked flask, add isolongifanone (2mmol) successively, semicarbazide hydrochloride (2mmol), dehydrated alcohol 20mL, heated and stirred.Appropriate concentrated sulfuric acid catalyst is added after being heated to reflux temperature, reaction 12 ~ 24h (adopting LC-MS tracking monitor), naturally room temperature is placed to after question response completes, underpressure distillation removing ethanol, use 100mL acetic acid ethyl dissolution, the saturated sodium-chloride continuous washing of 100mL 5 times, through anhydrous sodium sulfate drying, filter, revolve steaming after use 95% ethyl alcohol recrystallization, obtain isolonglifolane base semicarbazone after purifying.
2) semicarbazone compounds and ethyl bromoacetate (or ethyl chloroacetate) carry out cyclization, generate corresponding thiazolone compounds.Concrete reaction equation is:
Concrete operations are: in 150mL round-bottomed flask, add (10.0mmol) isolonglifolane base semicarbazone, equimolar amount (10.0mmol) ethyl bromoacetate, equivalent (10.0mmol) sodium acetate, 80mL dehydrated alcohol, 8-12h (LC-MS tracking monitor) is stirred at 78 DEG C, react completely to revolve and steam removing ethanol, dissolve with methylene dichloride, after saturated sodium-chloride washing extraction, anhydrous sodium sulfate drying, obtains product isolonglifolane oxazolones after revolving steaming, 95%EtOH recrystallization.
Characterize prepared isolonglifolane oxazolones product, result is as follows:
Molecular formula is C
18h
27n
3o
2, molecular weight is 317.21, white solid (yield 95%); M.p.202 DEG C; IR (KBr) ν: 3432.84 (v
n-H, NH
2), 2995.74 (v
asC-H, CH
3), 2869.04 (v
asC-H, CH
2), 1726.12 (V
sC-O, C=O), 1647.04 (v
asC-H, CH
3), 1594.21 (v
sC-N, C-N), 1560.16 (v
s, C=N), 1456.71 (v
sC-H, CH
3), 1369.05 (v
sC-H, CH
2), 1303.26 (v
sC-H, CH
3), 1230.09 (V
sC-O, C=O), 693.65 (v
ρ, CH
2) cm
-1;
1h NMR (600MHz, CDCl
3) δ: 0.922 (s, 3H, 1-CH
3), 0.999 (s, 3H, 1-CH
3), 2.533-2.643 (m, 1H, 2-CH), 1.156-1.178 (m, 2H, 3-CH
2), 1.035 (s, 3H, 5-CH
3), 1.090 (s, 3H, 5-CH
3), 1.254-1.269 (m, 2H, 6-CH
2), 1.386-1.402 (d, J=9.6Hz, 2H, 7-CH
2), 0.842 (s, 1H, 9-CH
2), 1.604-1.618 (d, J=8.4Hz, 2H, 10-CH
2), 1.956-2.026 (m, 2H, 11-CH
2), 1.702 (s, 1H, NH), 4.039 (s, 2H, CH
2);
13c NMR (150MHz, CDCl
3) δ: 24.453,24.905,24.941,25.803,27.656,27.924,32.576,33.359,36.711,43.398,43.620,58.857,107.578,127.716,128.943; LCMS calcd for C
18h
27n
3o
2[M+H
+] 317.21, found:318.7; Anal.cald for C
18h
27n
3o
2: C68.11, H8.57, N 13.24, S 10.08; Found C 68.11, H 8.57, N 113.24, S 8.085.
Embodiment 2
Isolonglifolane oxazolones is tested the inhibit activities of Human umbilical vein endothelial cells (HUVECs) Inflammatory response.
1, cell culture processes: with having in the DMEM substratum of 10% calf serum, cultivator huve cell.Put into CO
2in incubator, cultivate (37 DEG C, 5%CO
2, 95% air, keep certain humidity environment), the situation of growth of observation of cell under inverted microscope.According to cell actual state, change liquid; After cultivating 1 ~ 2d, namely cell becomes individual layer, and then 0.25% tryptic digestion, goes down to posterity by 1:3.The Human umbilical vein endothelial cells growing into individual layer is adopted in experimentation.
2, the foundation of experimental model and grouping: first use 0.25% trypsin digestion and cell, add the DMEM substratum having 10% calf serum.Blow and beat into single cell suspension with dropper, cell is inoculated in 96 well culture plates, inoculum density is 5 × 10
4individual/mL, every pore volume is 200 μ L; Then plate is transferred in cell incubation case and carries out cultivating (37 DEG C, 5%CO
2, 95% air, keep certain moisture), spend the night, within 2nd, be replaced with new substratum.Adding final concentration in cell plate is that the LPS of 2 μ g/mL is hatched 24h and caused inflammatory damage model.
96 hole steril cell culture plates are divided into 6 groups, if normal group, model group, positive drug acetylsalicylic acid group (10 μMs), A low concentration group (1 μM), concentration group (10 μMs) in A, A high density group (100 μMs), often organizes 8 holes.Before modeling, positive drug acetylsalicylic acid and A incubate HUVECs 24h in advance, and normal group and model group add isopyknic PBS.After administration, model group, positive drug acetylsalicylic acid group and the modeling according to the method described above of A group.
The bioactive mensuration of compound: carry out HUVECs cultivation according to 1 method, carries out HUVECs modeling according to 2 methods.96 hole steril cell culture plates are divided into 6 groups, if normal group, model group, positive drug acetylsalicylic acid group (10 μMs), A low concentration group (1 μM), concentration group (10 μMs) in A, A high density group (100 μMs), often organizes 8 holes.Before modeling, positive drug acetylsalicylic acid and A incubate HUVECs 24h in advance, and normal group and model group add isopyknic PBS.After modeling, suck substratum in 96 orifice plates, add and do not add MTT solution (5mg/mL) 20 μ L again containing hole every after the substratum 180 μ L of serum, on 37 DEG C of shaking tables, temperature incubates 4 hours, then sucks the substratum containing MTT, every hole adds DMSO liquid 200 μ L, hatch 10min, every hole is got 150 μ L and is moved in 96 orifice plates, and microplate reader 490nm detects the OD value in each hole, with the survival condition of OD value reflection cell, and calculate cell survival rate (%).
Cell survival rate (%)=each hole OD
490value/normal group OD
490value mean × 100%
The survival rate of table 1 HUVECs compares
Note: in table, NA representative does not have biological activity; ▲ bioactive the data that represent this compound compare p < 0.05 with model group, and the ▲ ▲ biological activity number that represents this compound compares p < 0.01 with model group; The biological activity number that * represents this compound compares p < 0.01 with blank group.
Can be obtained by table 1: compound isolonglifolane oxazolones has good anti-inflammatory activity to HUVECs cell.
Claims (6)
1. isolonglifolane oxazolones, is characterized in that: structural formula is
molecular formula is C
18h
27n
3o
2, molecular weight is 317.21, and states of matter is white solid, and m.p. is 202 DEG C.
2. the synthetic method of isolonglifolane oxazolones according to claim 1, is characterized in that, comprise the following steps:
1) under an acidic catalyst effect, isolongifanone and semicarbazide hydrochloride in organic solvent, react under reflux temperature, obtain semicarbazone;
2) under an acidic catalyst effect, semicarbazone and halogenated acetic acids ethyl ester, in organic solvent, react 8 ~ 12h under reflux temperature, obtain isolonglifolane oxazolones.
3. the synthetic method of isolonglifolane oxazolones according to claim 2, is characterized in that, comprise below step:
1) in the there-necked flask being furnished with agitator and thermometer, add dehydrated alcohol successively, isolongifanone, semicarbazide hydrochloride, the vitriol oil, heating reflux reaction 12-24h, obtains semicarbazone;
2) in the there-necked flask being furnished with agitator and thermometer, add dehydrated alcohol successively, semicarbazone, halogenated acetic acids ethyl ester, an acidic catalyst, be heated to reflux temperature reaction 8-12h, obtain isolonglifolane oxazolones.
4. the synthetic method of isolonglifolane oxazolones according to Claims 2 or 3, it is characterized in that, described an acidic catalyst is sodium acetate.
5. the synthetic method of isolonglifolane oxazolones according to Claims 2 or 3, it is characterized in that, described halogenated acetic acids ethyl ester is ethyl bromoacetate or ethyl chloroacetate.
6. isolonglifolane oxazolones according to claim 1 is preparing the application in anti-inflammatory drug.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105294598A (en) * | 2015-11-24 | 2016-02-03 | 南京林业大学 | Isolongifolene[1,2,3]thiadiazole compound and preparation method and application thereof |
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| CN103951566A (en) * | 2014-04-30 | 2014-07-30 | 南京林业大学 | N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound as well as synthetic method and application thereof |
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| CN103951566A (en) * | 2014-04-30 | 2014-07-30 | 南京林业大学 | N-alkyl-1,2,3,4,5,6-hexahydro-1,1,5,5-tetramethyl-7H-2,4 alpha-methanonaphthalene-7-amine compound as well as synthetic method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105294598A (en) * | 2015-11-24 | 2016-02-03 | 南京林业大学 | Isolongifolene[1,2,3]thiadiazole compound and preparation method and application thereof |
| CN105294598B (en) * | 2015-11-24 | 2017-09-15 | 南京林业大学 | Isolonglifolene base [1,2,3] thiadiazole compound and its preparation method and application |
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