CN100338008C - 1-carboxy-1-(3,5-dimethoxy phenyl)-2-(4-R group phenyl) ethano and preparation method thereof - Google Patents
1-carboxy-1-(3,5-dimethoxy phenyl)-2-(4-R group phenyl) ethano and preparation method thereof Download PDFInfo
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- CN100338008C CN100338008C CNB2005100390183A CN200510039018A CN100338008C CN 100338008 C CN100338008 C CN 100338008C CN B2005100390183 A CNB2005100390183 A CN B2005100390183A CN 200510039018 A CN200510039018 A CN 200510039018A CN 100338008 C CN100338008 C CN 100338008C
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Abstract
The present invention relates to 1-carboxy-1-(3, 5-dimethoxyphenyl)-2-(4-R group phenyl) ethylene and a preparation method thereof, which belongs to the field of organic chemistry and pharmaceutical chemistry. The 1-carboxy-1-(3, 5-dimethoxyphenyl)-2-(4-R group phenyl) ethylene has a general formula of *, wherein the R represents hydrogen, hydroxyl, nitryl, alkoxyl, etc. The compound has the preparation method that 3, 5-dimethoxyphenylacetic acid reacts with corresponding para orientation R ylbenzaldehyde. The products of the 1-carboxy-1-(3, 5-dimethoxyphenyl)-2-(4-R group phenyl) ethylene are derivates of 1, 2-diphenyl ethylene, which are similar to Pterostibene. The compound of the present invention is a new compound and can be used in the medical field of tumor prevention, oxidation prevention, etc.
Description
Technical field
1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-R base phenyl) ethene and preparation method thereof relates to the derivative of a class stilbene, belongs to organic chemistry and pharmaceutical chemistry field.
Background technology
1989, the epidemiology survey result of world's cardiovascular disorder Controlling System that The World Health Organization (WHO) is presided over showed that Frenchman's evidence of coronary heart diseases and mortality ratio are than other western countries, and be especially much lower than American and Englishman.Although the saturated fatty acid that the Frenchman uses almost is four times in American and Englishman, it is the latter's 1/3rd that the Frenchman suffers from cardiopathic danger.This phenomenon is called as " French antinomy ".Studies show that this phenomenon is that the whole world maximum Production of Wine and country of consumption are closely related with France.Analyze its reason, may be because in fine grape wine, there be a kind of material that is called trans-resveratrol, it has important nourishing function to human body.
Trans-resveratrol (resveratrol, chemical structure is shown in structural formula 1), a kind of derivative of stilbene, its chemistry by name 3,4 ', 5-trihydroxy--trans-stilbene (3,4 ', 5-trihydroxystilbene), be colourless needle crystal, be soluble in organic solvents such as ether, chloroform, methyl alcohol, ethanol, acetone, ethyl acetate.
Resveratrol
resveratrol
Structural formula 1
In the root of Tuber Fleeceflower Root, find trans-resveratrol in 1963 first, in grape vine, also detected this compound in 1976.Found afterwards that it mainly was present in grape leaf and the skin, content is few in the pulp.The trans-resveratrol that approximately contains 50～100mg/g in the fresh Pericarpium Vitis viniferae.At present at least in 72 kind of plant of 31 genus of 21 sections, trans-resveratrol and glucoside thereof have been found.Along with going deep into to trans-resveratrol research, it is found that it has multiple pharmacologically active, as: antitumous effect, influence to cardiovascular systems, anti-microbial effect, in drinks with the collaborative antioxygenation of flavonoid, anti-aging effects, estrogen effect, protect the liver, sharp liver effect, antibechic, antiasthmatic effect, hypotensive activity or the like, particularly result of study shows, trans-resveratrol is promptly initial in 3 stages that cancer takes place, in enhancement and the expansion process, bigger anti-cancer activity is all arranged, and all there is restraining effect etc. in 3 stages that cancer takes place, caused the extensive concern of Chinese scholars.
1997, [Jang M such as Jang, Cai L, Udeani GO, et al.Cancer chemopreventiveactivity of resveratrol, a natural product derived from grapes.Science, 1997,275 (5297): 218] having delivered them on U.S.'s science (Science) magazine is the result of study of object with the mouse, make mouse suffer from skin carcinoma by manual method, it takes resveratrol 2 all reliefs, the back discovery of 18 weeks, cancer cell can reduce 98% at most, minimumly reduces 68%.For the mouse mammary gland culture through carcinogenic processing, trans-resveratrol can suppress the development that preceding infringement takes place tumour in addition.And in mouse skin cancer model, trans-resveratrol can stop the development of tumour.
1998, [Clement MV such as the scientist Clement of NUS, Hirpara JL, Chawdhury SH, et al.Chemopreventive agent Resveratrol, a natural product derivedfrom grapes, triggers CD95 signaling-dependent apoptosis in human tumor cells.Blood, 1998,92 (3): 996] discover, trans-resveratrol can be induced the cracking of human HL60 leukemia cell DNA, and causes membrane phospholipid to lose its asymmetry, shows that trans-resveratrol can induce human HL60 leukemia cell's programmed death.After the trans-resveratrol effect 48 hours, the death of neoplastic cells rate surpasses 80%.Research is also found, cancer cell death depends on the interaction of CD95-CD95L, and trans-resveratrol increases the expression of CD95L in HL60 cell and the T47D mastocarcinoma cell, it is by reaching the purpose of carcinogenic cells in the fatal position to the CD95 of tumour cell and the CD95L expression balance of immunocyte, in case trigger, the CD95 acceptor will activate a series of cascade reactions in the born of the same parents.Scientist finds again with trans-resveratrol mastocarcinoma to be carried out same processing, and the CD95-CD95L system reaches a new level as a result, after 18 hours, can cause 63% T47D mastocarcinoma necrocytosis.These results of study show that the growth effect of mechanism of resveratrol inhibiting cancer cells has more than the cancer that is limited to a certain type.
2000, [Manna SK such as Manna, Mukhopadhyay A, Aggarwal BB.Resveratrolsuppresses TNF-induced activation of nuclear transcription factors NF-kappa B, activatorprotein-1, and apoptosis:potential role of reactive oxygen intermediates and lipidperoxidation.J Immunol, 2000,164 (12): 6509] and [Holmes-McNaryM such as Holmes-McNary, Baldwin AS Jr.Chemopreventive properties of trans-resveratrol are associated withinhibition of activation of the I κ B kinase.Cancer Res, 2000,60:3477] find that then resveratrol can block the activation of tumour necrosis factor (TNF) inductive nuclear factor κ B (NF-κ B) with dosage and time-dependent mode, suppress the p65 subunit phosphorylation of TNF inductive NF-κ B and the reporter gene of nuclear translocation and NF-κ B dependence and transcribe, can also block by Buddhist ripple ester, lipopolysaccharides, H
2O
2, inductive NF-κ B such as okadaic acid, ceramide activation, also suppress TNF inductive MAPKK (mitogen activated protein kinase) and the kinase whose activation of c-Jun N-terminal.
Calendar year 2001, [Ahmad N such as Ahmad, Adhami VM, Afaq, et al.Resveratrol causesWAF-1/p21-mediated G (I)-phase arrest of cell cycle and induction of apoptosis inhuaman epidermoid careinoma A431 cells.Clin Cancer Res, 2001,7 (5): 1466] the report resveratrol can inducing cell cyclin deopendent protein kinase (CDK) arrestin p21
WAF-1Generation, and can reduce the protein expression of cyclin (cyclin) D1, D2, E and CDK2, CDK4, CDK6, and then cause the G of people's epidermal carcinoma A431 cell
1Phase pauses, and cell can not be finished from G
1Phase is to the conversion of S phase, and thinks that this process is irreversible, will finally cause apoptosis.
In sum, this extensively is present in the crude substance of occurring in nature resveratrol, has been proved to have comparatively sure antitumor action, is a kind of natural antitumor prodrug that gets a good chance of.But as the medicine of treatment cancer, the effect of resveratrol is strong not enough.Therefore, be necessary its structure is further transformed, in the hope of finding to have the compound of more pretending usefulness.In recent years, existing abroad scholar has begun the research work of resveratrol derivative.2002, [Agnes MR such as American scholar Agnes MR, Muriel C, Cristian D, et al.Cancer chemopreventive and antioxidant activities of pterostibene, a naturally occurringanalogue of Resveratrol.J.Agric.Food Chem, 2002,50:3453] studied the natural analog 3 of resveratrol, 5-dimethoxy-4 ' '-(pterostibene is as structure for hydroxyl-trans-stilbene
Pterostibene
Structural formula 2
Shown in the formula 2) antitumour activity and anti-oxidant activity.The result shows that pterostibene also has the obvious suppression effect to cyclooxygenase (COX-1).2003, David AL[David A.Learmonth.A concise synthesisof the 3-O-β-D-and 4 '-β-D-glucuronide conjugates of trans-Resveratrol.Bioconjugate Chem.2003,14:262] the 3-position of having reported at resveratrol and 4 '-position introduces the study on the synthesis of glucuronic acid glucoside, in the hope of further its effect of research.
Summary of the invention
The objective of the invention is all have certain antitumour activity based on resveratrol and its analogue pterostibene, and they all belong to 1, the derivative of 2-toluylene, for this reason, design voluntarily and prepared the analogue that a class has the pterostibene of different chemical structures, in the hope of finding to have than the higher anti-tumor activity of Pterostibene or the new compound of anti-oxidant activity.
Technical scheme of the present invention:
The analogue of pterostibene of the present invention is 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-R base phenyl) ethene, and its general structure is shown in general structure 3:
General structure 3
R wherein represents hydrogen, methoxyl group, nitro, hydroxyl etc.
The preparation feedback of the compound of general structure 3 of the present invention is shown in reaction formula 1:
Reaction formula 1
Its preparation method is: with 3,5-dimethoxy benzyl bromine and sodium cyanide carry out cyanation and make 3, the 5-dimethoxybenzeneacetonitrile, 3, the hydrolysis of 5-dimethoxybenzeneacetonitrile obtains 3,5-dimethoxyphenylacetic acid, 3,5-dimethoxyphenylacetic acid and contraposition R benzaldehyde carry out the toluylene reaction and make product 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-R base phenyl) ethene;
A. cyanation: 0.2mol sodium cyanide and 50 ml waters are added in the there-necked flask, stir and make the solid dissolving, adds 50 milliliters of dehydrated alcohols, be warming up to 65 ℃, adding 0.2mol 3,5-dimethoxy benzyl bromine was 65 ℃ of insulation reaction 1.5 hours.Reaction solution is poured out, separated out solid after being chilled to room temperature, filter, get white needle-like crystals 3 with the methanol recrystallization, the 5-dimethoxybenzeneacetonitrile;
B, hydrolysis reaction: in there-necked flask, add 0.1mol 3,50 milliliters of 5-dimethoxybenzeneacetonitrile and methyl alcohol, stirring heats up makes the solid dissolving, adds 25 ml waters and 0.3-0.4mol sodium hydroxide down at 50 ℃, continues to be warming up to backflow, reacted 5 hours, transfer to pH1～2 with concentrated hydrochloric acid, standing over night is separated out solid, filter, use recrystallizing methanol, get colourless acicular crystal 3, the 5-dimethoxyphenylacetic acid;
C. toluylene reaction: in there-necked flask, add 0.01mol 3, the 5-dimethoxyphenylacetic acid, 15 milliliters of contraposition R benzaldehyde 0.01mol and acetic anhydrides, stirring is warming up to 40 ℃ and treats the solid dissolving, adds 0.01mol salt of wormwood, continues reaction 2.5 hours, be chilled to room temperature, transfer pH to 1～2 with hydrochloric acid, standing over night leaches solid, get 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-R base phenyl) ethene with 95% ethyl alcohol recrystallization.
Beneficial effect of the present invention: product 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-R base phenyl) ethene is the analogue of Pterostibene, in the hope of finding to have the new compound of the antitumor or anti-oxidant activity higher, be used for medical fields such as antitumor, anti-oxidant than Pterostibene.
Specific embodiments
The preparation of embodiment 1:1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-p-methoxy-phenyl) ethene (3a)
3, the preparation of 5-dimethoxybenzeneacetonitrile (1):
9.8 gram sodium cyanides and 50 ml waters are added 250 milliliters of there-necked flasks, stir and make the solid dissolving, adds 50 milliliters of dehydrated alcohols, be warming up to 65 ℃, add 40 and restrain 3,5-dimethoxy benzyl bromine was 65 ℃ of insulation reaction 1.5 hours.Reaction solution is poured out, is separated out solid after being chilled to room temperature, filter, crude product, get white needle-like crystals 23 with the methanol recrystallization and restrain 3,5-dimethoxybenzeneacetonitrile, 51～53 ℃ of fusing points.
3, the preparation of 5-dimethoxyphenylacetic acid (2):
At 150 milliliters of there-necked flasks, add 3,50 milliliters of 5-dimethoxybenzeneacetonitrile (1) 17.7 gram and methyl alcohol, stirring heats up makes the solid dissolving.Add 25 ml waters and sodium hydroxide 15 grams down at 50 ℃, continue to be warming up to backflow, reacted 5 hours.Transfer to pH1～2 with concentrated hydrochloric acid, standing over night is separated out solid, filters.Use recrystallizing methanol, get colourless acicular crystal 3,5-dimethoxyphenylacetic acid (2) 16.2 grams, 100～102 ℃ of fusing points.
The preparation of 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-p-methoxy-phenyl) ethene (3a):
At 150 ml flasks, add 3,5-dimethoxyphenylacetic acid (2) 1.96 grams, 15 milliliters of aubepine 1.36 grams and acetic anhydrides, stirring is warming up to 40 ℃ and treats the solid dissolving, adds salt of wormwood 0.7 gram, continues to react 2.5 hours.Be chilled to room temperature, transfer pH to 1～2, standing over night with hydrochloric acid.Solid is leached, get pale yellow powder 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-p-methoxy-phenyl) ethene (3a) 2.0 grams, 184～186 ℃ of fusing points with 95% ethyl alcohol recrystallization.
The preparation of embodiment 2:1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-phenyl ethene (3b)
Employing embodiment 1 similar method, by 3,5-dimethoxyphenylacetic acid (2) 1.96 grams and 1.1 gram phenyl aldehydes reactions get white powder solid 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-phenyl ethene (3b) 1.7 grams, 203～205 ℃ of fusing points.
The preparation of embodiment 3:1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-nitrophenyl) ethene (3c)
Adopt embodiment 1 similar method, by 3,5-dimethoxyphenylacetic acid (2) 1.96 grams and 1.5 gram 4-nitrobenzoyl aldehyde reactions get yellow needle-like crystal 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-and 2-(4-nitrophenyl) ethene (3c) 2.2 grams, 226～228 ℃ of fusing points.
The preparation of embodiment 4:1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-hydroxy phenyl) ethene (3d)
Adopt embodiment 1 similar method, by 3,5-dimethoxyphenylacetic acid (2) 1.96 grams and 1.2 gram p-Hydroxybenzaldehyde reactions get faint yellow solid 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-and 2-(4-hydroxy phenyl) ethene (3d) 1.5 grams, 223～225 ℃ of fusing points.
Claims (6)
1,1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-R base phenyl) ethene, its general structure is as follows:
R wherein represents hydrogen, methoxyl group, nitro, hydroxyl.
2. derivative according to claim 1, wherein R is a hydrogen, compound name is called 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-phenyl ethene.
3. derivative according to claim 1, wherein R is a methoxyl group, compound name is called 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-p-methoxy-phenyl) ethene.
4. derivative according to claim 1, wherein R is a nitro, compound name is called 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-nitrophenyl) ethene.
5. derivative according to claim 1, wherein R is a hydroxyl, compound name is called 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-hydroxy phenyl) ethene.
6. 1-carboxyl-1-(3 according to claim 1, the 5-Dimethoxyphenyl)-preparation method of 2-phenyl ethene derivatives, it is characterized in that with 3 5-dimethoxy benzyl bromine and sodium cyanide carry out cyanation and make 3, the 5-dimethoxybenzeneacetonitrile, 3, the hydrolysis of 5-dimethoxybenzeneacetonitrile obtains 3,5-dimethoxyphenylacetic acid, 3,5-dimethoxyphenylacetic acid and contraposition R benzaldehyde carry out the toluylene reaction and make product 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-phenyl ethene derivatives;
A, cyanation: 0.2mol sodium cyanide and 50 ml waters are added there-necked flask, stir and make the solid dissolving, adds 50 milliliters of dehydrated alcohols, be warming up to 65 ℃, adding 0.2mol 3,5-dimethoxy benzyl bromine was 65 ℃ of insulation reaction 1.5 hours.Reaction solution is poured out, separated out solid after being chilled to room temperature, filter, get white needle-like crystals 3 with the methanol recrystallization, the 5-dimethoxybenzeneacetonitrile;
B, hydrolysis reaction: in there-necked flask, add 0.1mol 3,50 milliliters of 5-dimethoxybenzeneacetonitrile and methyl alcohol, stirring heats up makes the solid dissolving, adds 25 ml waters and 0.3-0.4mol sodium hydroxide down at 50 ℃, continues to be warming up to backflow, reacted 5 hours, transfer to pH1～2 with concentrated hydrochloric acid, standing over night is separated out solid, filter, use recrystallizing methanol, get colourless acicular crystal 3, the 5-dimethoxyphenylacetic acid;
C. toluylene reaction: in there-necked flask, add 0.01mol 3, the 5-dimethoxyphenylacetic acid, 15 milliliters of contraposition R benzaldehyde 0.01mol and acetic anhydrides, stirring is warming up to 40 ℃ and treats the solid dissolving, adds 0.01mol salt of wormwood, continues reaction 2.5 hours, be chilled to room temperature, transfer pH to 1～2 with hydrochloric acid, standing over night leaches solid, get 1-carboxyl-1-(3, the 5-Dimethoxyphenyl)-2-(4-R base phenyl) ethene with 95% ethyl alcohol recrystallization.
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| CN101948381A (en) * | 2010-09-06 | 2011-01-19 | 南京师范大学 | Novel antineoplastic compound |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5430062A (en) * | 1992-05-21 | 1995-07-04 | Research Corporation Technologies, Inc. | Stilbene derivatives as anticancer agents |
| CN1539805A (en) * | 2003-10-24 | 2004-10-27 | 中国科学院广州化学研究所 | Method for synthesizing pterostilbene |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5430062A (en) * | 1992-05-21 | 1995-07-04 | Research Corporation Technologies, Inc. | Stilbene derivatives as anticancer agents |
| CN1539805A (en) * | 2003-10-24 | 2004-10-27 | 中国科学院广州化学研究所 | Method for synthesizing pterostilbene |
Non-Patent Citations (1)
| Title |
|---|
| Cancer chemopreventive and antioxidant activities ofpterostibene,a naturally occurring analogue of Resveratrol. Agnes MR et al,J. Agric. Food Chem,Vol.50 2002 * |
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