CN102351848A - Rotenone cyclopropanecarboxamide and its preparation method and use - Google Patents
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- CN102351848A CN102351848A CN2011102268482A CN201110226848A CN102351848A CN 102351848 A CN102351848 A CN 102351848A CN 2011102268482 A CN2011102268482 A CN 2011102268482A CN 201110226848 A CN201110226848 A CN 201110226848A CN 102351848 A CN102351848 A CN 102351848A
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- UHOGWUDLNDOOPV-WPSQETHBSA-N CC([C@@H]1Oc2ccc(C(C34c(cc(c(OC)c5)OC)c5OCC3C4)=O)c(OC)c2C1)=C Chemical compound CC([C@@H]1Oc2ccc(C(C34c(cc(c(OC)c5)OC)c5OCC3C4)=O)c(OC)c2C1)=C UHOGWUDLNDOOPV-WPSQETHBSA-N 0.000 description 1
- HTUMJQCCXZQXAY-LOACHALJSA-N CC([C@H](CC(C1)COc(cc2[O](C)C)c1cc2OC)CC=C1)=C1O Chemical compound CC([C@H](CC(C1)COc(cc2[O](C)C)c1cc2OC)CC=C1)=C1O HTUMJQCCXZQXAY-LOACHALJSA-N 0.000 description 1
- DQPVKMXVNLBFQK-SGAUDOEVSA-N CC1(C2(C)c(cc(c(OC)c3)OC)c3OC1)Oc1c(C[C@H](C(C)=C)O3)c3ccc1C2=O Chemical compound CC1(C2(C)c(cc(c(OC)c3)OC)c3OC1)Oc1c(C[C@H](C(C)=C)O3)c3ccc1C2=O DQPVKMXVNLBFQK-SGAUDOEVSA-N 0.000 description 1
- BNMCPQJHABZPMJ-UHFFFAOYSA-N Cc(cc(c(OC)c1)OC)c1O Chemical compound Cc(cc(c(OC)c1)OC)c1O BNMCPQJHABZPMJ-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention discloses rotenone cyclopropanecarboxamide. A chemical structural formula of rotenone cyclopropanecarboxamide is shown in the formula I, wherein R is selected from a hydrogen group, a methyl group or an ethyl group. The invention also discloses a preparation method of rotenone cyclopropanecarboxamide which is shown in the formula 1A and has a chemical name of 5,6-dimethoxy-N-[(R)-4-methoxy-2-(propenyl-2-yl)-2,3-dihydrobenzofuran-5-yl]-1,1a,2,7b-tetrahycyclopropa[c]benzofuran-7b-amide. The preparation method is characterized in that rotenone and oxygen-sulfur ylide undergo open-loop rearrangement, then are etherified by dimethyl sulphate, are oximated by hydroxylamine hydrochloride, and undergo Beckmann rearrangement in the presence of acetyl chloride as a catalyst. A crystal structure of rotenone cyclopropanecarboxamide shown in the formula 1A is characterized in that the crystal structure belongs to a triclinic system and a space group P1. The invention also discloses a use of rotenone cyclopropanecarboxamide in preparation of a drug for treating the human lung cancer or the human liver cancer.
Description
Technical field
The present invention relates to a kind of new compound and its production and application, specifically is trifoliate jewelvine ring propionic acid amide and its production and application.
Background technology
Tubatoxin is early stage people a kind of compounds with insecticidal activity that extraction separation comes out from plant roots such as Derris, be one of three great tradition botanical pesticide [pesticide plant and botanical pesticide. the 2nd edition. Beijing: Chinese agriculture press, 2004].Because the insecticidal spectrum of tubatoxin is wide, residual period is short, be difficult for developing immunity to drugs, to the person poultry safety with help promoting advantage such as the eubiosis; Make tubatoxin as environment friendly agricultural have very great development potentiality [Chinese Plants property pesticide developing prospect. agricultural chemicals; 2003,42 (3): 1]; Chinese patent [CN 101805333] has been described the anti-tumor activity of Cyclorotenoid.
The present invention is the trifoliate jewelvine ring propionic acid amide of the synthetic a kind of novel structure of raw material with the tubatoxin, and the gained compound is carried out structural characterization, active testing.Preliminary bioactivity research result shows: trifoliate jewelvine ring propionic acid amide has better antitumor activity.
Summary of the invention
The object of the present invention is to provide the trifoliate jewelvine ring propionic acid amide shown in the chemical structural formula I:
Wherein, R is selected from: hydrogen, methyl or ethyl.
Trifoliate jewelvine ring propionic acid amide (I A, R=CH
3) chemical name is 5,6-dimethoxy-N-[(R)-4-methoxyl group-2-(propylene-2-yl)-2,3-Dihydrobenzofuranes-5-yl]-1,1a, 2,7b-tetrahydrochysene ring third is [c] chromene-7b-acid amides also.
The present invention also provides the preparation method of the compound shown in the formula I A; It is characterized in that; Preparing method with the compound shown in the formula I A is that tubatoxin and the open loop of oxygen sulfur ylide are reset, and again through the methyl-sulfate etherificate, oxammonium hydrochloride oximate and acyl chlorides catalysis Beckmann rearrangement obtain:
The present invention also provides the crystalline structure of the compound shown in the formula I A.The molecular formula of trifoliate jewelvine ring propionic acid amide I A is C
25H
27N0
6, molecular weight 437.48, crystal belongs to triclinic(crystalline)system, spacer P1; A=9.5772 (5)
B=10.6591 (6)
C=13.0112 (7)
Z=2, V=1134.29 (11)
D
c=1.281g/cm
3, F (000)=464, μ=0.092mm
-1, 3415 considerable measuring points [I＞2 σ (I)], the final discrepancy factor R=0.038 of considerable measuring point refine, wR=0.111.Trifoliate jewelvine ring propionic acid amide I A crystalline structure atom is numbered as follows:
The present invention also provides the compound shown in the formula I to have anti-tumor activity, can be used for preparing antitumor drug.
The present invention compared with prior art has following advantage:
1. select oxygen sulfur ylide and tubatoxin open loop to reset first, through the methyl-sulfate etherificate, oxammonium hydrochloride oximate and acyl chlorides catalysis Beckmann rearrangement obtain trifoliate jewelvine ring propionic acid amide (I):
Wherein, R is selected from: hydrogen, methyl or ethyl.
2. measured the crystalline structure of the compound shown in the formula I A first.The molecular formula of trifoliate jewelvine ring propionic acid amide I A is C
25H
27NO
6, molecular weight 437.48, crystal belongs to triclinic(crystalline)system, spacer P1; A=9.5772 (5)
B=10.6591 (6)
C=13.0112 (7)
Z=2, V=1134.29 (11)
D
c=1.281g/cm
3, F (000)=464, μ=0.092mm
-1, 3415 considerable measuring points [I＞2 σ (I)], the final discrepancy factor R=0.038 of considerable measuring point refine, wR=0.111.
Trifoliate jewelvine ring propionic acid amide for human lung carcinoma cell (A549 cell) or human liver cancer cell (Bel 7402 cells), have and suppress active, can be used for preparing antitumor drug.
Description of drawings
Fig. 1 is a trifoliate jewelvine ring propionic acid amide I A crystalline molecular structure.
Fig. 2 is trifoliate jewelvine ring propionic acid amide I A crystalline crystal accumulation figure.
Embodiment
Following examples are intended to illustrate the present invention rather than to further qualification of the present invention.
The preparation of embodiment 1 trifoliate jewelvine ring propionic acid amide I A
1) preparation of oxygen sulfur ylide: add 2g NaH and 10mL sherwood oil in the there-necked flask, nitrogen protection is stirred 10min down, topples over then sherwood oil, repeats to wash twice again, revolves steaming, removes fully until sherwood oil.Add the 0.05mol Trimethylsulfoxonium Iodide, nitrogen protection is stirred 4h under the room temperature, gets milky white emulsion, i.e. oxygen sulfur ylide.
2) the preparation 0.02mol tubatoxin of compound 2 is dissolved among the 20mLDMF, under nitrogen protection, joins in the homemade oxygen sulfur ylide, and 20 ℃ are reacted 30min down, and reaction solution is washed with saturated common salt, crosses to filter thick product; The dehydrated alcohol recrystallization, product, yield 85.5%, m.p.132～134 ℃,
(c=0.2, CHCl
3);
1HNMR (CDCl
3, 400MHz) δ: 1.33 (d, 1H, 1a-CH
3), 1.76 (s, 3H, 9-CH
3), 1.93 (b, 2H, 1-CH
2), 3.01 (m, 1H, 3-CH
2), 3.36 (m, 1H, 3-CH
2), 3.63 (s, 3H, OCH
3), 3.83 (s, 3H, OCH
3), 4.21 (d, 1H, J=11.6Hz, 2-CH
2), 4.35 (d, 1H, J=11.6Hz, 2-CH
2), 4.94 (s, 1H ,=CH
2), 5.08 (s, 1H ,=CH
2), 5.32 (t, 1H, J=8.0Hz, 2-CH), 6.26 (d, 1H, J=8.4Hz, 7-H), 6.44 (s, 1H, 4-H), 6.49 (s, 1H, 7-H), 7.64 (d, 1H, J=8.4Hz, 6-H), 12.7 (d, 1H, J=10.4Hz, OH).
3) the preparation 0.01mol 2 of compound 3 is dissolved in the 40mL methylene dichloride, 0.35g four butyl bromation amine, the sodium hydroxide solution of 2mL 30%; Stirring and refluxing 30min; Add the 2g methyl-sulfate, stirring and refluxing 4h, reaction solution washing; Dichloromethane extraction; Anhydrous sodium sulfate drying revolves dried faint yellow solid 4.00g, yield 94.2%; M.p.53～55 ℃
(c=0.2, CHCl
3);
1H NMR (CDCl
3, 400MHz) δ: 1.26 (m, 1H, 1a-CH), 1.73 (s, 3H, 9-CH
3), 2.01 (m, 1H, 1-CH
2), 2.35 (m, 1H, 1-CH
2), 3.03 (m, 1H, 3-CH
2), 3.38 (m, 1H, 3-CH
2), 3.44 (d, 3H, J=3.6Hz, 6-OCH
3), 3.53 (d, 3H, J=8.4Hz, 4-OCH
3), 3.79 (d, 3H, J=2.4Hz, 5-OCH
3), 4.21 (d, 1H, J=10.8Hz, 2-CH
2), 4.31 (d, 1H, J=9.6Hz, 2-CH
2), 4.92 (s, 1H ,=CH
2), 5.05 (d, 1H, J=3.6Hz ,=CH
2), 5.17 (q, 1H, J=8.0Hz, 2-CH), 6.38 (d, 1H, J=7.6Hz, 7-H), 6.43 (s, 1H, 4-H), 6.55 (dd, 1H, J=12Hz, J=8.0Hz, 7-H), 7.64 (d, 1H, J=4.2Hz, J=7.6Hz, 6-H).
4) the preparation 0.01mol 3 of compound 4 is dissolved in the 50mL ethanol solution, adds the 0.04mol oxammonium hydrochloride, back flow reaction 24h, the reaction solution washing is filtered, drying, column chromatography, white solid 2.43g, yield 55.5%, m.p.99～101 ℃;
1H NMR (CDCl
3, 400MHz) δ: 1.14 (m, 1H, 1-CH
2), 1.45 (m, 1H, 1-CH
2), 1.70 (m, 1H, 1a-CH
2), 1.78 (d, J=5.6Hz, 3H, isopropenyl-CH
3), 3.44 (m, 1H, dihydrofuran ring 3-CH
2), 3.49 (m, 1H, dihydrofuran ring 3-CH
2), 3.66 (d, J=15.6Hz, 3H, 6-OCH
3), 3.79 (s, 3H, 4-OCH
3) 3.82 (s, 3H, 5-OCH
3), 3.99 (dd, 1H, J=4Hz, J=10Hz, 2-CH
2), 4.28 (d, 1H, J=9.6Hz, 2-CH
2), 4.94 (s, 1H, isopropenyl=CH
2), 5.10 (d, J=5.2Hz, 1H, isopropenyl=CH
2), 5.21 (dt, 1H, dihydrofuran ring 2-CH), 6.47 (s, 1H, 4-H), 6.51 (dd, 1H, J=0.8Hz, J=8.4Hz, 7-H) 6.55 (d, J=6.4Hz, 1H, 7-H), 7.40 (dd, J=5.2Hz, J=8.4Hz, 1H, 6-H).
5) add the 0.4g ketoxime in the preparation 100mL there-necked flask of trifoliate jewelvine ring propionic acid amide I A, the 20mL methylene dichloride stirs under the room temperature, adds Acetyl Chloride 98Min.; Continue reaction 30min, reaction solution washing, extraction, drying; The ether recrystallization gets white solid 0.31g, 138～140 ℃ of fusing points, yield 77.5%;
1H-NMR (CDCl
3, 400MHz) δ: 0.96 (m, 1H, 1a-CH
2), 1.75 (d, 3H, J=6.4Hz, 9-CH
3), 2.04 (m, 1H, 1-CH
2), 2.18 (dd, 1H, J=4,4Hz, J=8.8Hz, 1-CH
2), 3.11 (m, 1H, 3-CH
2), 3.46 (m, 1H, 3-CH
2), 3.71 (s, 3H, OCH
3), 3.80 (dd, 1H, J=5.6Hz, J=11.6Hz, 2-CH
2), 3.86 (s, 6H, 2 * OCH
3), 4.55 (m, 1H, 2-CH
2), 4.91 (s, 1H ,=CH
2), 5.07 (s, 1H ,=CH
2), 5.13 (t, 1H, J=8.8Hz, 2-CH), 6.50 (d, 1H, J=8.8Hz, 7-H), 6.56 (s, 1H, 7-H), 7.02 (s, 1H, 4-H), 8.05 (d, 1H, J=8.8Hz, 6-H), 8.09 (s, 1H, NH).
The crystalline structure of embodiment 2 trifoliate jewelvines ring propionic acid amide I A
The X-ray structure is measured
Select 0.46mm × 0.40mm × 0.34mm single crystal, in BRUKER? SMART? APEX1000? CCD diffractometer diffraction data collected using graphite monochromated The Mo? Kα radiation (λ = 0.71073?
), in 298K under ω-?
Scanning diffraction data collected at 2.1 ° ≤ θ ≤ 26.0 ° range of collecting 8754 data, independent reflections 4353, point 3415 can be observed.The SAINTPLUS program of using Bruker then uses the SADABS program to carry out the experience absorption correction reduction of data simultaneously.Application SHELXS-97 and SHELXL-97 program [Sheldrick, GMSHELXS97? And? SHELXL97, University? Of?
Germany, 1997] direct method structure solution and refinement.All non-hydrogen atoms adopt the complete matrix method of least squares to carry out structure refinement.All non-hydrogen atoms are all done the anisotropy refine.Theoretical hydrogenation, the correction of hydrogen atom isotropy thermal parameter.The molecular formula of trifoliate jewelvine ring propionic acid amide I A is C
25H
27NO
6, molecular weight 437.48, crystal belongs to triclinic(crystalline)system, spacer P1; A=9.5772 (5)
B=10.6591 (6)
C=13.0112 (7)
Z=2, V=1134.29 (11)
D
c=1.281g/cm
3, F (000)=464, μ=0.092mm
-1, 3415 considerable measuring points [I＞2 σ (I)], the final discrepancy factor R=0.038 of considerable measuring point refine, wR=0.111.Crystal data and structural parameter are seen table 1.
Crystal data and the structural parameter of table 1. trifoliate jewelvine ring propionic acid amide I A
Trifoliate jewelvine ring propionic acid amide I A crystalline molecular structure as shown in Figure 1; The structure cell accumulation graph as shown in Figure 2.
The anti-tumor activity of embodiment 3 trifoliate jewelvines ring propionic acid amide
1. anti-tumor activity principle
The mtt assay biological activity test is claimed the MTT colorimetry again, is a kind of method that detects cell survival and growth.The MTT analytical method is with viable cell metabolite reductive agent tetrazolium bromide [3-(4,5-dimethyl-2-thiazole)-2,5-phenylbenzene bromination tetrazole; 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide, MTT] be the basis.MTT is a kind of dyestuff that can accept hydrogen atom.Desaturase relevant with NADP in the viable cell plastosome can change into xanchromatic MTT insoluble hepatic first a ceremonial jade-ladle, used in libation (formazon) in cell, dead cell does not then have this function.Behind DMSO dissolving formazon, under certain wavelength, measure optical density value with microplate reader, both can quantitatively measure the survival rate of cell.According to the variation observation sample of optical density value restraining effect to tumour cell.
2. anti-tumor activity experiment
Sample: trifoliate jewelvine ring propionic acid amide.
Clone: hepatoma cell line Bel 7402; Lung cancer cell line A549 (the Xiangya Medical College, Zhongnan Univ cell bank provides).
Reagent: tetrazolium bromide (MTT), RPMI RPMI-1640, new-born calf serum, microbiotic (U.S. hero Life Technologies, Inc.); Pancreatin (U.S. AMRESCO company); 96 well culture plates (U.S. hero Life Technologies, Inc.); Dimethyl sulfoxide (DMSO) (U.S. Sigma company).
Instrument: HFsafe-1500 type Bechtop, HF151UV type CO
2Incubator (Shanghai Lishen Scientific Equipment Co., Ltd.); XSP-15C type inverted microscope (the rectangular opticinstrument in Shanghai company limited); MultiskanMK3 type microplate reader (U.S. Thermo company); Ultrapure water preparing instrument (U.S. Milli-Q company).
Experimental implementation: sample is for the test of Bel7402 cell and A549 cell.The experimental implementation process of every kind of cell is identical; In the experimentation; Per sample (p.s.) is provided with 5 concentration gradients (0.025mmol/L, 0.05mmol/L, 0.1mmol/L, 0.25mmol/L and 0.5mmol/L); Four parallel samples of each concentration; Test parallel 3 times for every group, and reach a conclusion through the blank control group contrast.Microplate reader detects each hole OD value, detects wavelength 570nm.
3. anti-tumor activity evaluation
1) cell inhibitory rate calculates:
2) IC
50Value is calculated
Sample solution concentration logarithmic value and cell inhibitory rate linear regression utilize the half-inhibition concentration IC of computed in software sample pair cell
50Value.Trifoliate jewelvine ring propionic acid amide is for the IC of Bel 7402 cells and A549 cell
50Be respectively 0.103mmol/L and 0.122mmol/L.
Test result shows that trifoliate jewelvine ring propionic acid amide to be tested has the activity of inhibition for human lung carcinoma cell (A549 cell) or human liver cancer cell (Bel 7402 cells), can be used for preparing anti-people's lung cancer or people's liver-cancer medicine.
Claims (4)
1. the trifoliate jewelvine shown in the chemical structural formula I encircles propionic acid amide:
Wherein, R is selected from: hydrogen, methyl or ethyl.
2. the preparation method of the ring of the trifoliate jewelvine shown in chemical structural formula I A propionic acid amide is characterized in that tubatoxin and the open loop of oxygen sulfur ylide rearrangement, and again through the methyl-sulfate etherificate, oxammonium hydrochloride oximate and acyl chlorides catalysis Beckmann rearrangement obtain; The preparation feedback formula is following:
The chemical name of the trifoliate jewelvine ring propionic acid amide shown in the I A is 5,6-dimethoxy-N-[(R)-4-methoxyl group-2-(propylene-2-yl)-2,3-Dihydrobenzofuranes-5-yl]-1,1a, 2,7b-tetrahydrochysene ring third is [c] chromene-7b-acid amides also.
3. the crystalline structure of the ring of trifoliate jewelvine shown in the said I A of claim 2 propionic acid amide is characterized in that it belongs to triclinic(crystalline)system, spacer P1; A=9.5772 (5)
B=10.6591 (6)
C=13.0112 (7)
Z=2, V=1134.29 (11)
D
c=1.281g/cm
3, F (000)=464, μ=0.092mm
-1, 3415 considerable measuring points [I＞2 σ (I)], the final discrepancy factor R=0.038 of considerable measuring point refine, wR=0.111.
4. the application of claim 1 said trifoliate jewelvine ring propionic acid amide in the anti-people's lung cancer of preparation or people's liver-cancer medicine.
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| CN103588760A (en) * | 2013-10-22 | 2014-02-19 | 湖南大学 | N-[1-(benzofuran-5-yl)alkyl]benzopyran-4-amide as well as preparation method and application of N-[1-(benzofuran-5-yl)alkyl]benzopyran-4-amide |
| CN103588761A (en) * | 2013-10-22 | 2014-02-19 | 湖南大学 | Preparation and application of N-[1-(benzofuran-5-yl)-2-oxoethyl]benzopyran-4-amide |
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| CN104642314A (en) * | 2015-02-04 | 2015-05-27 | 宁波工程学院 | Application of N-furan phenol methyl ether-5-yl) chromene-4-amide as sterilizing agent |
| CN104642314B (en) * | 2015-02-04 | 2017-05-17 | 宁波工程学院 | Application of N-furan phenol methyl ether-5-yl) chromene-4-amide as sterilizing agent |
| CN105198866A (en) * | 2015-06-01 | 2015-12-30 | 宁波工程学院 | Cyclopropyl derris hydrazide and application thereof to preparation of neuraminidase inhibitor |
| CN105198866B (en) * | 2015-06-01 | 2018-03-16 | 宁波工程学院 | Ring the third trifoliate jewelvine hydrazides and its application as neuraminidase inhibitor |
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