CN102702058A - Preparation method of 4-methoxy-cinnamaldehyde thiosemicarbazone - Google Patents
Preparation method of 4-methoxy-cinnamaldehyde thiosemicarbazone Download PDFInfo
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Abstract
The invention provides a preparation method of 4-methoxy-cinnamaldehyde thiosemicarbazone, and relates to a thiosemicarbazone compound. The molecular formula of the 4-methoxy-cinnamaldehyde thiosemicarbazone is C11H13N3OS. The preparation method comprises the following steps of: weighing and dissolving thiosemicarbazone in a solvent, adding 4-methoxy-cinnamaldehyde with the same quality as that od thiosemicarbazone, stirring under the action of magnetic force, adding a proper amount of glacial acetic acid, heating, reflux reacting, then cooling a reaction system to the room temperature, standing for crystallizing, and filtering to obtain a crude product; and recrystallizing the crude product to obtain the product 4-methoxy-cinnamaldehyde thiosemicarbazone.
Description
Technical field
The present invention relates to a kind of (thiosemicarbazone) compound, especially relate to a kind of preparation method of 4-methoxy-cinnamaldehyde thiosemicarbazone.
Background technology
(thiosemicarbazone) compound is the schiff bases compounds that is formed by thiosemicarbazide and corresponding aldehydes or ketones condensation, and it has wide biological activity, receives much concern at medicine and pharmacology and chemical field.Li Jinzhou ([1] Li Jinzhou; Zhang Guanglin; Sha Jingquan; Synthetic, spectral characterization and biological activity [J] Deng. furancarbonyl pyrazolone thiosemicarbazone title complex. spectroscopy and spectroscopic analysis, 2005,25 (2): 216-219) discover that furancarbonyl pyrazolone thiosemicarbazone all has good inhibitory effect to staphylococcus aureus, Bacillus subtilus, intestinal bacteria, soft rot of cabbage bacterium and Kidney bean meat or fish vaccine etc.; Richardson ([2] Richardson D R.Therapeutic potential of iron chelators in cancer therapy [J] .Adv.Exp.Med.Biol.; 2002; 509:231-249) point out that (thiosemicarbazone) compound is fabulous ribonucleoside diphosphate reductase (RR) suppressor factor; Through inhibition, influence the synthetic of DNA and repair, thereby have anti-tumor activity RR; ([3] Jiang Z G such as Jiang Z G; Lebowitz M S; Ghanbari H A.Neuroprotective activity of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (PAN-811), a cancer therapeutic agent [J] .CNS Drug Rev., 2006; Research 12:77-90) shows: 3-amino-2-pyridine aldehydes thiosemicarbazone (3-AP; PAN-811) not only have antitumor action, and in the treatment of cerebral ischemia disease, play neuroprotective, its mechanism of action is for reducing gathering of calcium ion and reactive oxygen species.Simultaneously; As metal chelator, but thiosemicarbazone chelating different metallic forms metal complexes, is applied to analytical chemistry field ([4] Lu Qin; Wang Guoxiong; Yin Zhanfeng waits the research [J] of .N-pyridine oxide-2-formaldehyde thiosemicarbazone cobalt complex. Chinese Journal of Inorganic Chemistry, 1991.7 (1): 65-68).In the recent period, Zhu Yu-jing [waits ([5] Zhu Y J, Song K K; Li Z C, et al.Antityrosinase and antimicrobial activities of trans-cinnamaldehyde thiosemicarbazone [J] .J.Agri.Food Chem.2009,57:5518-5523) at first studied cinnamaldehyde thiosemicarbazone to the inhibition mechanism of Mushroom Tyrosinase with and anti-microbial activity; Separating earlier, industry waits ([6] Xie Xianye; Jiang Lin, Xue Chaobin, etc. the synthetic inhibition active [J] that reaches the insect phenol oxidase of substituted benzaldehyde thiosemicarbazone. chemical reagent; 2007.29 (1): 34-36) part substituted benzaldehyde thiosemicarbazone has been synthesized in design; And it is active to have studied its inhibition to the insect phenol oxidase, and experimental result shows that (thiosemicarbazone) compound has good inhibition active to phenol oxidase.
Phenol oxidase (phenoloxidase, EC.1.14.18.1 are called for short PO) is to be present in the intravital a kind of copper bearing metalloenzyme of insect, is the key enzyme of synthesis of melanin in the organism, to the growth of insect, the crucial enzyme that growth plays an important role.Phenol oxidase catalysis L-tyrosine hydroxylation changes the L-DOPA into and oxidation L-DOPA forms the DOPA quinone, and the DOPA quinone forms protectiveness melanochrome after series reaction.Simultaneously; This enzyme also with the insect molting process in tan and turn into relevant; Be that insect relies in a kind of important enzyme ([7] Ashida M, Yamazaki H, the Biochemistry of the phenoloxidase system in insect:with special reference to its activation.Ohnishi E of existence; Ishizaki H. (eds) [M] Molting and Metamorphosis.1990, Tokyo:Japan Science Society Press.239-261).Zhang Zong Ping ([8] Zhang Zong Ping, cold glad husband. insecticide virulence and application [M]. Beijing: chemical press, 1993;: 331-337) point out: an approach the most likely exploring new insecticide is biological reasonable approach, and wherein " former tyrosinase inhibitor " and " tanning process suppressor factor " is listed in first and second position. existing research ([9] Xue Chaobin, Wang Qin; Luo Wanchun; Deng. cupferron is to the restraining effect [J] of cabbage caterpillar polyphenoloxidase. the insect journal, and 2005,48 (1): 290-294) result shows; The phenol oxidase suppressor factor can hinder insect tanning when casting off a skin through the inhibitory enzyme vigor and turn usefulness into, thereby reaches its insecticidal action.With the target spot development of new efficient pesticides of polyphenoloxidase as biological pesticide, can significantly reduce the usage quantity of biological pesticide, the residual of agricultural chemicals minimized, can obtain very high economic benefit again.Therefore; Research and design is the phenol oxidase suppressor factor efficiently; Not only has important significance for theories; Can be used as the novel agrochemical of " environmental friendliness " simultaneously and have important practice significance and application prospect ([7] shida M, Yamazaki H, Biochemistry of the phenoloxidase system in insect:with special reference to its activation.Ohnishi E; Ishizaki H. (eds) [M] Molting and Metamorphosis.1990, Tokyo:Japan Science Society Press.239-261).
Heilbron, I.M., Hudson, H.E., Huish, Doris M et al. ([10] Heilbron, I.M.; Hudson, H.E.; Huish; Doris M.The reversed phototropy of cinnamaldehyde semicarbazone and its methoxy derivatives [J] .J.Chem.Soc.; Trans.; 123,2273-2279.) synthesized the 4-methoxy-cinnamaldehyde thiosemicarbazone first, and studied its anti-phtotropism effect in nineteen twenty-three.Bernstein, J., Yale, Harry L. and Toldy, L.; Nogradi, T.; Vargha, L. etc. are respectively at nineteen fifty-one ([11] Bernstein, J.; Yale, Harry L., Losee; K.et al.The chemotherapy of experimental tuberculosis.III.The synthesis of thiosemicarbazones and related compounds [J] .J.Amer.Chem.Soc.73 is 906-912.) with ([12] Toldy, L. in 1954; Nogradi, T., Vargha; L.et al.Antituberculous agents.I.Thiosemicarbazones and hydrazides [J] .Acta.Chim.Hung. 4.302-313) has reported the tuberculosis effect of this compound.Yet for this compound as the novel pesticide target proteins---the application of the suppressor factor of phenol oxidase does not appear in the newspapers as yet.
Summary of the invention
The purpose of this invention is to provide a kind of compound---the preparation method of 4-methoxy-cinnamaldehyde thiosemicarbazone.
The molecular formula of 4-methoxy-cinnamaldehyde thiosemicarbazone according to the invention is C
11H
13N
3OS, the structural formula of 4-methoxy-cinnamaldehyde thiosemicarbazone is:
At normal temperatures, the 4-methoxy-cinnamaldehyde thiosemicarbazone is soluble in DMSO, is slightly soluble in methyl alcohol, ethanol etc.; The result of ir spectra shows, 1680cm
-1The absorption peak of C=O near disappears, and at 1602cm
-1The absorption peak that C=N occurs; The molecular weight of 4-methoxy-cinnamaldehyde thiosemicarbazone is m/z 235.1 (M+H
+, CH
3OH); The result of proton nmr spectra is following:
1H?NMR(DMSO-d6，TMS，400MHz)：δ(ppm)11.35(HN，s)，7.90(CH，s)，7.48~6.91(C
6H
4，4H，d)，8.21,7.62(NH
2，s)，3.76(CH
3O,s)，6.70,6.75(CH=CH,d)。
The preparation method of 4-methoxy-cinnamaldehyde thiosemicarbazone according to the invention may further comprise the steps:
1) take by weighing thiosemicarbazide and be dissolved in the solvent, the 4-methoxycinnamic aldehyde of adding and thiosemicarbazide equivalent under the magnetic agitation, adds an amount of Glacial acetic acid min. 99.5, behind the heating reflux reaction reaction system is cooled to room temperature, leaves standstill crystallization, and suction filtration obtains crude product;
2), obtain product 4-methoxy-cinnamaldehyde thiosemicarbazone with the crude product recrystallization.
The temperature of said heating reflux reaction is preferably 60～70 ℃, and the time of heating reflux reaction is preferably 3～5h.
4-methoxy-cinnamaldehyde thiosemicarbazone according to the invention can be used in the sterilant target proteins phenol oxidase.
At normal temperatures, products therefrom 4-methoxy-cinnamaldehyde thiosemicarbazone is soluble in DMSO, is slightly soluble in methyl alcohol, ethanol etc.
Reaction product adopts ir spectra, mass spectrum and nuclear magnetic resonance spectrum that its structure is identified (ir spectra is as shown in Figure 1, and mass spectrum is as shown in Figure 2, and nuclear magnetic resonance spectrum is as shown in Figure 3).The result of ir spectra shows, 1680cm
-1The absorption peak of C=O near disappears, and at 1602cm
-1The absorption peak that C=N occurs; The result of ESI-MS shows that the molecular weight of this compound is m/z 258.0 (M+Na
+, CH
3OH); The result of proton nmr spectra is following:
1H?NMR(DMSO-d6，TMS，400MHz)：δ(ppm)11.35(HN，s)，7.90(CH，s)，7.48~6.91(C
6H
4，4H，d)，8.21,7.62(NH
2，s)，3.76(CH
3O,s)，6.70,6.75(CH=CH,d)。
In conjunction with ir spectra, mass spectrum and proton nmr spectra data, confirm that synthetic compound is the 4-methoxy-cinnamaldehyde thiosemicarbazone.
Compare with the method for Bernstein etc., the preparation method of 4-methoxy-cinnamaldehyde thiosemicarbazone according to the invention with identical dissolution with solvents, helps the homogenization of reaction system with thiosemicarbazide and 4-methoxycinnamic aldehyde; In addition, the present invention's productive rate behind recrystallization is higher, reaches 77.1% (the Bernstein method is 70%).
With cabbage caterpillar phenol oxidase research object, measured retarding effect, the inhibition mechanism and inhibition type and inhibition parameter of 4-methoxy-cinnamaldehyde thiosemicarbazone to phenol oxidase.Experimental result shows: the 4-methoxy-cinnamaldehyde thiosemicarbazone has had strong inhibitory effects to phenol oxidase, and it causes concentration (half inhibiting rate, the IC of phenol oxidase vigor forfeiture 50%
50) be 1.62 μ mol/L, suppress mechanism and the enzyme amount is mapped with initial velocity of reaction, obtain one group of straight line that intersects at initial point, but explain that the 4-methoxy-cinnamaldehyde thiosemicarbazone shows as retroactive inhibition to the inhibition of phenol oxidase; Suppress the judgement of type and adopt Lineweaver-Burk double-reciprocal plot method, obtain one group of straight line that intersects at the Y axle, thereby judge that it suppresses type is competitive inhibition, the inhibition constant K is tried to achieve in the secondary mapping
I=0.94 μ mol/L.With reported phenol oxidase suppressor factor such as 4-hydroxy-benzoic acid (IC
50=11.3mmol/L), cupferron (IC
50=0.652mmol/L) and kojic acid (IC
50=0.468mmol/L) grade is compared, and it suppresses effect and has improved 69800,400 and 290 times respectively, and this result shows that it is the novel pesticide input application of target that the 4-methoxy-cinnamaldehyde thiosemicarbazone can be used as with the phenol oxidase.
Description of drawings
Fig. 1 is the infrared spectrogram of the said 4-methoxy-cinnamaldehyde thiosemicarbazone of the embodiment of the invention.In Fig. 1, X-coordinate is the wave number (cm of ir radiation
-1), ordinate zou is transmittance (%); Its main crest information is following:
Crest 2 wave number 3264.36cm
-1Intensity 12.40% is NH stretching vibration absorption peak;
Crest 3 wave number 3165.59cm
-1Intensity 12.40% is C-H stretching vibration absorption peak on the phenyl ring;
Crest 7 wave number 1258.73cm
-1Intensity 10.05% is C=S stretching vibration absorption peak;
Crest 8 wave number 1246.79cm
-1Intensity 11.31% is C-O stretching vibration absorption peak.
Fig. 2 is the ESI-MS mass spectrum of the said 4-methoxy-cinnamaldehyde thiosemicarbazone of the embodiment of the invention.In Fig. 2, X-coordinate is the specific charge (m/z) of compound molecule, and ordinate zou is an ion signal intensity (* 10
4); The specific charge of corresponding fragmention is 102.4,145.2,186.5,236.1,258.0,291.1,359.2 from left to right, and wherein 258.0 corresponding peaks are molion fragment (M+Na
+).
Fig. 3 is the proton nmr spectra of the said 4-methoxy-cinnamaldehyde thiosemicarbazone of the embodiment of the invention.In Fig. 3, X-coordinate is chemical displacement value (ppm); Chemical shift is respectively 11.340,8.136,7.893,7.869,7.604,7.583,7.499,7.477,6.955,6.944,6.921,6.916,6.754,6.731,6.714,6.691 from left to right, 3.758ppm.
Fig. 4 is the enlarged view of proton nmr spectra chemical shift 6.5～8.5 parts of the said 4-methoxy-cinnamaldehyde thiosemicarbazone of the embodiment of the invention.In Fig. 4, X-coordinate is chemical displacement value (ppm); Chemical shift is respectively 8.136,7.893,7.869,7.604,7.583,7.499,7.477,6.955,6.944,6.921,6.916,6.754,6.731,6.714 from left to right, 6.691ppm.
Fig. 5 is the retarding effect of the said 4-methoxy-cinnamaldehyde thiosemicarbazone of the embodiment of the invention to phenol oxidase.In Fig. 5, X-coordinate is [I] (concentration of 4-methoxy-cinnamaldehyde thiosemicarbazone, unit is μ mol/L), and ordinate zou is Relative Activity (a relative enzyme activity, unit is %).
Fig. 6 is the judgement of the said 4-methoxy-cinnamaldehyde thiosemicarbazone of the embodiment of the invention to the inhibition mechanism of phenol oxidase.In Fig. 6, X-coordinate is [E] (enzyme concn in the reaction system, unit is mg/L), and ordinate zou is that (enzymic catalytic reaction speed, unit is μ molLmin to ν
-1); Line 1,2,3,4,5 corresponding 4-methoxy-cinnamaldehyde thiosemicarbazone concentration are respectively 0,0.4,0.8,1.2 and 1.6 μ mol/L.
Fig. 7 is the inhibition type and inhibition Determination of Parameters of the said 4-methoxy-cinnamaldehyde thiosemicarbazone of the embodiment of the invention to phenol oxidase.In Fig. 7, X-coordinate is [S]
-1(inverse of the concentration of substrate L-DOPA in the reaction system, unit are μ mol
-1L), ordinate zou is v
-1(inverse of enzymic catalytic reaction speed, unit are μ mol
-1L
-1Min); Line 1,2,3,4,5 corresponding inhibitor concentration are respectively 0,0.4,0.8,1.2 and 1.6 μ mol/L.
Fig. 8 is the secondary mapping.In Fig. 8, X-coordinate is [I] (4-methoxy-cinnamaldehyde thiosemicarbazone concentration, μ mol/L), and ordinate zou is Slope (slope of 5 lines among Fig. 7).
Embodiment
1.4-the synthesis step of methoxy-cinnamaldehyde thiosemicarbazone
Take by weighing thiosemicarbazide 0.455g (5mmol), be dissolved in 10mL 95% ethanolic soln, add 95% ethanolic soln that contains 0.81g 4-methoxycinnamic aldehyde; Under the magnetic agitation, add the 2mL Glacial acetic acid min. 99.5, reflux; Thin-layer chromatography monitoring reaction process behind the reflux 3h, is cooled to room temperature with reaction system; Leave standstill crystallization, suction filtration, acquisition crude product in 4 ℃.
Adopt 50% ethyl alcohol recrystallization, obtain product, oven drying is weighed, and calculating productive rate is 77.1%.Adopt mass spectrum, ir spectra and nuclear magnetic resonance spectrum to identify the structure of products therefrom; The infrared spectrogram of 4-methoxy-cinnamaldehyde thiosemicarbazone is referring to Fig. 1; The ESI-MS mass spectrum of 4-methoxy-cinnamaldehyde thiosemicarbazone is referring to Fig. 2; The proton nmr spectra of 4-methoxy-cinnamaldehyde thiosemicarbazone is referring to Fig. 3, and the enlarged view of proton nmr spectra chemical shift 6.5～8.5 parts of 4-methoxy-cinnamaldehyde thiosemicarbazone is referring to Fig. 4.
2.4-methoxy-cinnamaldehyde thiosemicarbazone is to the restraining effect of cabbage caterpillar phenol oxidase
The extraction reference [9] of cabbage caterpillar phenol oxidase, the phenol oxidase that this experiment is used is not purified.In the 2mL reaction system; 1.8mL contain the 0.1mmoL/L of 1mmol/L substrate L-DOPA phosphoric acid buffer (PBS, pH=6.8) in, add 200 μ L crude enzyme liquids; Use Beckman DU650 spectrophotometer; 37 ℃ of constant temperature are measured the OD value growth straight line in time of 475nm down, try to achieve enzyme activity from the collinear slope, and optical extinction coefficient is by (ε=3700M
-1Cm
-1) calculating .DMSO final concentration all is 3.33%, and its influence to enzyme of eliminating in contrast. enzyme activity unit (U) is defined as under this condition, and PM produces the enzyme amount of 1 μ mol/L product.The 4-methoxy-cinnamaldehyde thiosemicarbazone to the retarding effect of phenol oxidase referring to Fig. 5.
3.4-methoxy-cinnamaldehyde thiosemicarbazone is to the judgement of the inhibition mechanism of cabbage caterpillar phenol oxidase
In above-mentioned enzyme activity determination system; The concentration of immobilized substrate L-DOPA is 1mmol/L; Change the volume that adds crude enzyme liquid; Use Beckman DU650 spectrophotometer, the vigor of enzyme under the 4-methoxy-cinnamaldehyde thiosemicarbazone effect of the 37 ℃ of following mensuration of constant temperature different concns, optical extinction coefficient is by (ε=3700M
-1Cm
-1), calculate enzymic catalytic reaction speed.The 4-methoxy-cinnamaldehyde thiosemicarbazone to the judgement of the inhibition mechanism of phenol oxidase referring to Fig. 6., obtain one group of straight line that intersects at initial point, but explain that the 4-methoxy-cinnamaldehyde thiosemicarbazone shows as retroactive inhibition to the inhibition of phenol oxidase the mapping of enzymic catalytic reaction speed with the enzyme amount.
4.4-methoxy-cinnamaldehyde thiosemicarbazone is to the inhibition type and the mensuration that suppresses constant of cabbage caterpillar phenol oxidase
In above-mentioned enzyme activity determination system; The immobilized enzyme amount is constant, changes the concentration that adds substrate L-DOPA, uses Beckman DU650 spectrophotometer; The vigor of enzyme under the 4-methoxy-cinnamaldehyde thiosemicarbazone effect of the 37 ℃ of following mensuration of constant temperature different concns, optical extinction coefficient is by (ε=3700M
-1Cm
-1); Calculating enzymic catalytic reaction speed. the inverse with concentration of substrate is mapped to the inverse of enzymic catalytic reaction speed; Obtain one group of straight line that intersects at the Y axle; Thereby judge that it suppresses type is competitive inhibition, the 4-methoxy-cinnamaldehyde thiosemicarbazone to the inhibition type of phenol oxidase with suppress Determination of Parameters referring to Fig. 7.With of the concentration secondary mapping (referring to Fig. 8) of gained collinear slope, try to achieve the inhibition constant K to the 4-methoxy-cinnamaldehyde thiosemicarbazone
I=0.94 μ mol/L.
Claims (2)
1.4-the preparation method of methoxy-cinnamaldehyde thiosemicarbazone is characterized in that said 4-methoxy-cinnamaldehyde thiosemicarbazone molecular formula is C
11H
13N
3OS, the structural formula of 4-methoxy-cinnamaldehyde thiosemicarbazone is:
At normal temperatures, the 4-methoxy-cinnamaldehyde thiosemicarbazone is soluble in DMSO, is slightly soluble in methyl alcohol, ethanol; The result of ir spectra shows, 1680cm
-1The absorption peak of C=O near disappears, and at 1602cm
-1The absorption peak that C=N occurs; The molecular weight of 4-methoxy-cinnamaldehyde thiosemicarbazone is m/z 235.1 (M+H
+, CH
3OH); The result of proton nmr spectra is following:
1H?NMR(DMSO-d6，TMS，400MHz)：δ(ppm)11.35(HN，s)，7.90(CH，s)，7.48~6.91(C
6H
4，4H，d)，8.21,7.62(NH
2，s)，3.76(CH
3O,s)，6.70,6.75(CH=CH,d)；
Said preparation method may further comprise the steps:
1) take by weighing thiosemicarbazide and be dissolved in the solvent, the 4-methoxycinnamic aldehyde of adding and thiosemicarbazide equivalent under the magnetic agitation, adds an amount of Glacial acetic acid min. 99.5, behind the heating reflux reaction reaction system is cooled to room temperature, leaves standstill crystallization, and suction filtration obtains crude product;
2), obtain product 4-methoxy-cinnamaldehyde thiosemicarbazone with the crude product recrystallization.
2. the preparation method of 4-methoxy-cinnamaldehyde thiosemicarbazone as claimed in claim 1 is characterized in that in step 1), and the temperature of said heating reflux reaction is 60～70 ℃, and the time of heating reflux reaction is 3～5h.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB694688A (en) * | 1950-07-06 | 1953-07-22 | Bayer Ag | New chemotherapeutic thiosemicarbazones |
| US20090203747A1 (en) * | 2005-07-01 | 2009-08-13 | Trophos Parc Scientifique Luminy | Novel chemical compounds and the uses thereof as a medicine |
-
2009
- 2009-10-27 CN CN2012101568107A patent/CN102702058A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB694688A (en) * | 1950-07-06 | 1953-07-22 | Bayer Ag | New chemotherapeutic thiosemicarbazones |
| US20090203747A1 (en) * | 2005-07-01 | 2009-08-13 | Trophos Parc Scientifique Luminy | Novel chemical compounds and the uses thereof as a medicine |
Non-Patent Citations (5)
| Title |
|---|
| H.CECIL CALDWELL 等: "some amithiozone (tibione) analogs", 《JOURNAL OF THE AMERICAN PHARMACEUTICAL ASSOCIATION》 * |
| ISIDOR MORRIS HEILBRON 等: "studies in phototropy. The reversed phototropy of cinnamaldehydesemicarbazone and tis methoxy-derivatives", 《J.CHEM.SOC.TRANS.》 * |
| JACK BERNSTEIN 等: "The Chemotherapy of Experimental Tuberculosis. 111. The Synthesis of Thiosemicarbazones", 《J.AM.CHEM.SOC.》 * |
| W.LEWIS NOBLES 等: "Amithiozone (Tibione) analogs from aralkyl ketones", 《JOURNAL OF THE AMERICAN PHARMACEUTICAL ASSOCIATION》 * |
| YU-JING ZHU 等: "antityrosinase and antimicrobial activities of trans-cinnamaldehyde thiosemicarbazone", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
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