CN107880063B - Method for synthesizing subprostrate sophora - Google Patents
Method for synthesizing subprostrate sophora Download PDFInfo
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- CN107880063B CN107880063B CN201711269291.4A CN201711269291A CN107880063B CN 107880063 B CN107880063 B CN 107880063B CN 201711269291 A CN201711269291 A CN 201711269291A CN 107880063 B CN107880063 B CN 107880063B
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- dauricine
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- 238000000034 method Methods 0.000 title claims abstract description 9
- 241000219784 Sophora Species 0.000 title abstract description 6
- 230000002194 synthesizing effect Effects 0.000 title abstract 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000010189 synthetic method Methods 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- HUKSJTUUSUGIDC-ZBEGNZNMSA-N (-)-maackiain Chemical compound O1C2=CC=3OCOC=3C=C2[C@H]2[C@@H]1C1=CC=C(O)C=C1OC2 HUKSJTUUSUGIDC-ZBEGNZNMSA-N 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- HUKSJTUUSUGIDC-UHFFFAOYSA-N Trifolirhizin-aglykon Natural products O1C2=CC=3OCOC=3C=C2C2C1C1=CC=C(O)C=C1OC2 HUKSJTUUSUGIDC-UHFFFAOYSA-N 0.000 claims description 14
- AQASRZOCERRGBL-UHFFFAOYSA-N Dauricine Natural products CN1CCC2=CC(OC)=C(OC)C=C2C1CC1=CC=C(O)C(OC2=CC=C(C=C2)CC2N(C)CCC=3C=C(C(=CC=32)OC)OC)=C1 AQASRZOCERRGBL-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- AQASRZOCERRGBL-ROJLCIKYSA-N dauricine Chemical compound CN1CCC2=CC(OC)=C(OC)C=C2[C@H]1CC1=CC=C(O)C(OC2=CC=C(C=C2)C[C@H]2N(C)CCC=3C=C(C(=CC=32)OC)OC)=C1 AQASRZOCERRGBL-ROJLCIKYSA-N 0.000 claims description 12
- XCDMHEXDCIXKLK-UHFFFAOYSA-N Anhydrosophorol Natural products O1C2=CC=3OCOC=3C=C2C2=C1C1=CC=C(O)C=C1OC2 XCDMHEXDCIXKLK-UHFFFAOYSA-N 0.000 claims description 11
- YLZYAUCOYZKLMA-UHFFFAOYSA-N O-Methyl-maackiain Natural products O1C2=CC=3OCOC=3C=C2C2C1C1=CC=C(OC)C=C1OC2 YLZYAUCOYZKLMA-UHFFFAOYSA-N 0.000 claims description 11
- 239000003480 eluent Substances 0.000 claims description 10
- 229930008564 C01BA04 - Sparteine Natural products 0.000 claims description 9
- SLRCCWJSBJZJBV-UHFFFAOYSA-N alpha-isosparteine Natural products C1N2CCCCC2C2CN3CCCCC3C1C2 SLRCCWJSBJZJBV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 9
- SLRCCWJSBJZJBV-AJNGGQMLSA-N sparteine Chemical compound C1N2CCCC[C@H]2[C@@H]2CN3CCCC[C@H]3[C@H]1C2 SLRCCWJSBJZJBV-AJNGGQMLSA-N 0.000 claims description 9
- 229960001945 sparteine Drugs 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002012 dioxanes Chemical class 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 238000012805 post-processing Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 1
- ANJTVLIZGCUXLD-BDAKNGLRSA-N (-)-Cytisine Natural products C1NC[C@@H]2CN3C(=O)C=CC=C3[C@H]1C2 ANJTVLIZGCUXLD-BDAKNGLRSA-N 0.000 abstract description 5
- ANJTVLIZGCUXLD-DTWKUNHWSA-N cytisine Chemical compound C1NC[C@H]2CN3C(=O)C=CC=C3[C@@H]1C2 ANJTVLIZGCUXLD-DTWKUNHWSA-N 0.000 abstract description 5
- ANJTVLIZGCUXLD-UHFFFAOYSA-N ent-cytisine Natural products C1NCC2CN3C(=O)C=CC=C3C1C2 ANJTVLIZGCUXLD-UHFFFAOYSA-N 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 3
- 229930017327 cytisine Natural products 0.000 abstract description 2
- 229940027564 cytisine Drugs 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 230000006837 decompression Effects 0.000 description 6
- JXSLKTOGVPMPCS-UHFFFAOYSA-N tonkinensine B Natural products C1C(C2)C3=CC=CC(=O)N3CC1CN2CC1=C2OCC3C4=CC(OCO5)=C5C=C4OC3C2=CC=C1O JXSLKTOGVPMPCS-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- -1 alkaloid compound Chemical class 0.000 description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- LZEPVVDVBJUKSG-UHFFFAOYSA-N pterocarpan Chemical group C1=CC=C2C3COC4=CC=CC=C4C3OC2=C1 LZEPVVDVBJUKSG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 244000046101 Sophora japonica Species 0.000 description 1
- 235000010586 Sophora japonica Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003592 biomimetic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for synthesizing subprostrate sophora shown in formula (III) comprises the following steps: mixing cytisine shown in formula (I), Korean sophoricine shown in formula (II), formaldehyde and 4-dimethylamino pyridine in an organic solvent, reacting for 2-3 h at 85-95 ℃, and then carrying out post-treatment on a reaction solution to obtain a subprostrate shown in formula (III); the preparation process method is simple, short in time consumption and high in yield; the experimental result shows that the yield of the synthetic method can reach more than 73 percent;(I)(II)
Description
(1) technical field
The present invention relates to a kind of synthetic methods of alkaloid, and in particular to one kind has Cytisine-Pterocarpan bone
The synthetic method of the dauricine (Tonkinensine B) of frame.
(2) background technique
Dauricine (Tonkinensine B) is the alkaloid component being present in subprostrate sophora, chemical formula C28H26N2O6,
It is with Cytisine-Pterocarpan skeleton, and content is low in subprostrate sophora, and largely separation preparation has not been most from plant
Good selection.Pass through our early-stage study and Literature Consult, thus it is speculated that TonkinensineB this with Cytisine-
The biosynthesis precursor of the compound of Pterocarpan skeleton is respectively sparteine [(-)-cytisine] and maackiain
[(-)-maackiain], compound (-)-cytisine pass through methylation and oxidative coupling reaction and compound (-)-
Maackiain is connected, and the two precursor compounds content in subprostrate sophora is larger, largely isolated.
Pharmacological research finds that the alkaloid compound in subprostrate sophora has preferable pharmacological activity.It is traditional separation, pure
There are the shortcomings such as time-consuming, heavy workload in change method；Again because Structures of Natural Products is more complicated, if with total synthesis method
Synthetic route is long, and product yield is low, while being also possible to will use more noble metal catalyst, and the three-dimensional selection in reaction
Property often becomes very big obstacle, and the yield of final products is lower, is unfavorable for large scale preparation.With Cytisine-
The compound structure of Pterocarpan skeleton is more complicated, and chiral carbon is more, therefore fully synthetic extremely difficult.
(3) summary of the invention
Based on problems of the prior art, by the present invention in that with sparteine [(-)-cytisine] and Koryo
Chinese scholartree element [(-)-maackiain] is reactant, right using comparatively gentle reaction condition, as far as possible shortening reaction route
Cytisine-Pterocarpan skeleton carries out bio-mimetic syntheses, to realize a large amount of acquisition target compound dauricine
(Tonkinensine B) provides convenience for the further further investigation of the type compound.
Technical scheme is as follows:
A kind of synthetic method of dauricine shown in formula (III), the synthetic method carry out as follows:
Maackiain shown in sparteine shown in formula (I), formula (II), formaldehyde, 4-dimethylaminopyridine (DMAP) are being had
It is mixed in solvent, in 85~95 DEG C (preferably 93 DEG C) 2~3h of reaction, reaction solution is post-treated later, obtains product formula (III)
Shown dauricine.
Sparteine shown in the formula (I), maackiain, formaldehyde shown in formula (II), 4-dimethylaminopyridine the object that feeds intake
The ratio between amount of matter is 1.5~2:1:1.5~2:0.02~0.03；
The quality dosage of the organic solvent is 25~35 times of maackiain quality shown in formula (II)；
The formaldehyde is fed intake in the form of 37wt% aqueous solution；
The organic solvent is isopropanol or dioxanes；
The method of the reaction solution post-processing are as follows: after reaction, reaction solution is concentrated under reduced pressure, then with 200~300 mesh silicon
Glue carries out column chromatography for separation, using the methylene chloride/methanol mixed liquor of volume ratio 30:1 as eluant, eluent, collects containing target compound
Eluent, evaporating solvent under reduced pressure are simultaneously dry to get target product.
cytisine
maackiain
Tonkinensine B
The beneficial effects of the present invention are: compared with traditional extraction method, process of preparing of the present invention is simple, time-consuming
It is short, high income.The experimental results showed that synthetic method of the present invention, yield is up to 73% or more.
(4) Detailed description of the invention
Fig. 1: the hydrogen nuclear magnetic resonance spectrogram of Tonkinensine B prepared by embodiment 1.
(5) specific embodiment
Below by specific embodiment, the invention will be further described, but protection scope of the present invention is not limited in
This.
Embodiment 1
Maackiain (56.8mg, 0.2mmol) is dissolved in isopropanol (2ml), sparteine is sequentially added
(57.1mg, 0.3mmol), 37% formaldehyde (30ul contains formaldehyde 0.4mmol), DMAP (0.5mg, 0.004mmol), are returned in 85 DEG C
3h is flowed, after reaction, reaction solution decompression is spin-dried for, is separated with 200-300 mesh silicagel column, eluant, eluent is methylene chloride:
The mixed solvent of methanol=30:1 (volume ratio) collects the eluent containing target compound, and decompression is spin-dried for obtaining beige solid,
Product quality is 60.8mg, yield 62.5%.
1H-NMR (CDCl3,600MHz) δ: 7.28 (dd, J1=6.8Hz, J2=9.2Hz), 7.21 (d, J=8.4Hz),
6.70 (s), 6.52 (dd, J1=1.2Hz, J2=9.2Hz), 6.44 (d, J=8.4Hz), 6.40 (s), 5.98 (dd, J1=
1.2Hz, J2=6.8), 5.90 (d, J=1.6Hz), 5.88 (d, J=1.6Hz), 5.42 (d, J=6.4Hz), 5.29 (s),
4.17 (dd, J1=4.8Hz, J2=11.2Hz), 4.13 (br d, J=16.0Hz), 3.89 (dd, J1=6.4Hz, J2=
16.0Hz), 3.70 (d, J=14.4Hz), 3.66 (d, J=14.4 Hz), 3.55 (t, J=11.2Hz), 3.40 (m), 3.10
(br d, J=11.2Hz), 3.02 (m), 2.99 (m), 2.50 (br s), 2.44 (m), 2.39 (br d, J=11.2Hz),
1.95 (br, d, J=12.8Hz), 1.84 (br, d, J=12.8Hz)
Embodiment 2
Maackiain (56.8mg, 0.2mmol) is dissolved in dioxanes (2ml), sparteine is sequentially added
(57.1mg, 0.3mmol), 37% formaldehyde (30ul contains formaldehyde 0.4mmol), DMAP (0.5mg, 0.004mmol), are returned in 93 DEG C
2h is flowed, after reaction, reaction solution decompression is spin-dried for, is separated with 200-300 mesh silicagel column, eluent is methylene chloride:
The mixed solvent of methanol=30:1 (volume ratio) collects the eluent containing target compound, and decompression is spin-dried for obtaining beige solid,
Product quality is 67.8mg, yield 69.7%.
1H-NMR (CDCl3,600MHz) δ: 7.28 (dd, J1=6.8Hz, J2=9.2Hz), 7.21 (d, J=8.4Hz),
6.70 (s), 6.52 (dd, J1=1.2Hz, J2=9.2Hz), 6.44 (d, J=8.4Hz), 6.40 (s), 5.98 (dd, J1=
1.2Hz, J2=6.8), 5.90 (d, J=1.6Hz), 5.88 (d, J=1.6Hz), 5.42 (d, J=6.4Hz), 5.29 (s),
4.17 (dd, J1=4.8Hz, J2=11.2Hz), 4.13 (br d, J=16.0Hz), 3.89 (dd, J1=6.4Hz, J2=
16.0Hz), 3.70 (d, J=14.4Hz), 3.66 (d, J=14.4 Hz), 3.55 (t, J=11.2Hz), 3.40 (m), 3.10
(br d, J=11.2Hz), 3.02 (m), 2.99 (m), 2.50 (br s), 2.44 (m), 2.39 (br d, J=11.2Hz),
1.95 (br, d, J=12.8Hz), 1.84 (br, d, J=12.8Hz)
Embodiment 3
Maackiain (56.8mg, 0.2mmol) is dissolved in dioxanes (2ml), sparteine is sequentially added
(76.1mg, 0.4mmol), 37% formaldehyde (30ul contains formaldehyde 0.4mmol), DMAP (0.5mg, 0.004mol), are returned in 93 DEG C
2.5h is flowed, after reaction, reaction solution decompression is spin-dried for, is separated with 200-300 mesh silicagel column, eluent is dichloromethane
Alkane: the mixed solvent of methanol=30:1 (volume ratio) collects the eluent containing target compound, and it is solid that decompression is spin-dried for obtaining rice white
Body, product quality 71.6mg, yield 73.6%.
1H-NMR (CDCl3,600MHz) δ: 7.28 (dd, J1=6.8Hz, J2=9.2Hz), 7.21 (d, J=8.4Hz),
6.70 (s), 6.52 (dd, J1=1.2Hz, J2=9.2Hz), 6.44 (d, J=8.4Hz), 6.40 (s), 5.98 (dd, J1=
1.2Hz, J2=6.8), 5.90 (d, J=1.6Hz), 5.88 (d, J=1.6Hz), 5.42 (d, J=6.4Hz), 5.29 (s),
4.17 (dd, J1=4.8Hz, J2=11.2Hz), 4.13 (br d, J=16.0Hz), 3.89 (dd, J1=6.4Hz, J2=
16.0Hz), 3.70 (d, J=14.4Hz), 3.66 (d, J=14.4 Hz), 3.55 (t, J=11.2Hz), 3.40 (m), 3.10
(br d, J=11.2Hz), 3.02 (m), 2.99 (m), 2.50 (br s), 2.44 (m), 2.39 (br d, J=11.2Hz),
1.95 (br, d, J=12.8Hz), 1.84 (br, d, J=12.8Hz).
Claims (5)
1. a kind of synthetic method of dauricine shown in formula (III), which is characterized in that the synthetic method as follows into
Row:
Maackiain, formaldehyde, 4-dimethylaminopyridine shown in sparteine shown in formula (I), formula (II) are mixed in organic solvent
It closes, in 85~95 DEG C of 2~3h of reaction, reaction solution is post-treated later, obtains dauricine shown in product formula (III)；
Sparteine shown in the formula (I), maackiain, formaldehyde shown in formula (II), 4-dimethylaminopyridine the substance that feeds intake
The ratio between amount is 1.5~2:1:1.5~2:0.02~0.03；
The organic solvent is isopropanol or dioxanes；
2. the synthetic method of dauricine as described in claim 1, which is characterized in that reaction temperature is 93 DEG C.
3. the synthetic method of dauricine as described in claim 1, which is characterized in that the quality dosage of the organic solvent is formula
(II) 25~35 times of maackiain quality shown in.
4. the synthetic method of dauricine as described in claim 1, which is characterized in that the formaldehyde is with the shape of 37wt% aqueous solution
Formula feeds intake.
5. the synthetic method of dauricine as described in claim 1, which is characterized in that the method for the reaction solution post-processing are as follows:
After reaction, reaction solution is concentrated under reduced pressure, and then column chromatography for separation is carried out with 200~300 mesh silica gel, with the two of volume ratio 30:1
Chloromethanes/methyl alcohol mixed liquor is eluant, eluent, collects the eluent containing target compound, and evaporating solvent under reduced pressure is simultaneously dry to get mesh
Mark product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109970738A (en) * | 2019-02-27 | 2019-07-05 | 上海工程技术大学 | A kind of sparteine N- isoflavone compound and preparation method and application |
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| CN110804056B (en) * | 2019-11-06 | 2020-11-13 | 浙江工业大学 | Compound with cytisine-flavonoid skeleton and synthesis method and application thereof |
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2017
- 2017-12-05 CN CN201711269291.4A patent/CN107880063B/en active Active
Non-Patent Citations (1)
| Title |
|---|
| Tonkinensines A and B, two novel alkaloids from Sophora tonkinensis;Xing-Nuo Li et al.;《Tetrahedron Letters》;20080404;第49卷;第3797-3801页 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109970738A (en) * | 2019-02-27 | 2019-07-05 | 上海工程技术大学 | A kind of sparteine N- isoflavone compound and preparation method and application |
| CN109970738B (en) * | 2019-02-27 | 2021-07-09 | 上海工程技术大学 | Caragana N-isoflavone compound and preparation method and application thereof |
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