CN114773354B - Simple synthesis method of Trisphaeridine - Google Patents
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Abstract
The invention relates to a simple synthesis method of Trisphaeridine, which comprises the following specific steps: s1, dissolving 6-bromo-3, 4-methylene dioxybenzaldehyde and phenylboronic acid in a solvent, and adding K 2 CO 3 In N at 2 Adding Pd (OAC) under atmosphere 2 Performing Suzuki coupling reaction, purifying to obtain 6-phenylbenzo [ d][1,3]Dioxolane-5-carbaldehyde; s2, reacting 6-phenylbenzo [ d][1,3]Adding dioxolane-5-formaldehyde and ammonium formate into a photoreaction bottle, then adding 1, 3-hexafluoro-2-propanol, stirring to dissolve, then carrying out 6 pi electrocyclic reaction under the irradiation of visible light, and purifying after the reaction is finished to obtain the Trisphaeridine. The synthesis method disclosed by the invention is mild in reaction conditions, short in synthesis route, low in cost of required raw materials, free of toxic wastes and high in overall yield.
Description
Technical Field
The invention belongs to the technical field of heterocyclic compounds, and particularly relates to a simple synthesis method of Trisphaeridine.
Background
Cancer is one of the major diseases threatening human health at present, and it is counted that cancer is the second cause of death among residents of various countries worldwide, and thus, the development of drugs for treating cancer is urgently needed.
The benzophenanthridine natural alkaloid has wide physiological activity, and due to the fact that the special plane structure of the benzophenanthridine natural alkaloid can act on topoisomerase, the activity of the benzophenanthridine natural alkaloid in the aspect of tumor resistance is greatly concerned, and researches show that the benzophenanthridine natural alkaloid has wide anti-tumor activity and strong activity. Wherein Trisphaeridine is a relatively representative benzophenanthridineThe alkaloid can be isolated from Narcissus astricus (Narcissus asturiensis) belonging to Amaryllidaceae. Researchers find that the alkaloid has good inhibitory activity on human lung cancer cells A-549, human liver cancer cells hepg and human colon cancer cells ht-29 in the research process of the antitumor activity of the alkaloid, and the IC50 of the alkaloid is more than 40 mu mol.L -1 Indicating that Trisphaeridine has potential application in the treatment of these three types of cancer.
Therefore, a plurality of scientific researchers carry out synthetic research on Trisphaeridine so as to develop a simple, convenient, green and efficient synthetic route. At present, the synthetic methods of the alkaloid are many, but most of the methods need complicated steps, and the post-treatment is complex and is not environment-friendly. The method can synthesize the alkaloid through two simple reaction steps, has cheap and easily obtained raw materials, simple and convenient post-treatment, environmental protection, higher yield and lower comprehensive cost.
Disclosure of Invention
The invention aims to solve the technical problem of providing a simple synthesis method of Trisphaeridine aiming at the defects in the prior art, and the method has the advantages of being green, efficient, simple and convenient.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
the simple synthesis method of Trisphaeridine is provided, and the specific steps are as follows:
s1, dissolving 6-bromo-3, 4-methylenedioxybenzaldehyde (compound 1) and phenylboronic acid (compound 2) in a solvent, and adding K 2 CO 3 (for activating boric acid or boric acid ester to perform metal transfer reaction), stirring uniformly, and introducing N 2 In N at 2 Adding Pd (OAC) under atmosphere 2 Performing Suzuki coupling reaction, washing the reaction solution after the reaction is finished, extracting with ethyl acetate, collecting the organic phase, drying, concentrating, and purifying by column chromatography to obtain 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3);
s2, adding the 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde (compound 3) obtained in the step S1 and ammonium formate into a photoreaction bottle, then adding 1, 3-hexafluoro-2-propanol (HFIP, solvent), stirring and dissolving, then carrying out 6 pi electrocyclic reaction under visible light irradiation, concentrating the reaction solution after the reaction is finished, and purifying by column chromatography to obtain Trisphaeridine.
The synthetic route is as follows:
according to the scheme, the molar ratio of the 6-bromo-3, 4-methylenedioxybenzaldehyde described in S1 to phenylboronic acid is 1:0.9 to 1.4.
According to the scheme, the solvent in S1 is a mixed solution of N, N-Dimethylformamide (DMF) and water, and the volume ratio of the N, N-dimethylformamide to the water is 2-3: 1, the concentration of the 6-bromo-3, 4-methylenedioxybenzaldehyde in the solvent is 0.2-0.5 mol/L.
According to the scheme, S1 refers to K 2 CO 3 The molar ratio of the 6-bromo-3, 4-methylenedioxybenzaldehyde to the compound is 1:0.9 to 1.4.
According to the scheme, the Suzuki coupling reaction conditions of S1 are as follows: reacting for 3-5 hours at 20-30 ℃.
Following the above protocol, pd (OAC) as described in S1 2 The mol ratio of the formaldehyde to 6-bromo-3, 4-methylenedioxybenzaldehyde is 0.01-0.06: 1.
according to the scheme, the molar ratio of the 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde to the ammonium formate in S2 is 1:6 to 11.
According to the scheme, the concentration of the 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde in the 1, 3-hexafluoro-2-propanol S2 is 0.05-0.3 mol/L.
According to the scheme, the visible light source of S2 is a purple LED lamp, the power is 3-20W, and the wavelength is 400-420 nm.
According to the scheme, the 6 pi electrocyclization reaction condition of S2 is as follows: reacting for 10-12 hours at 20-35 ℃.
The invention has the beneficial effects that: the synthesis method of the invention has mild reaction conditions, short synthesis route, cheap raw materials, no toxic waste and high overall yield (the total yield is 27.3-46%).
Drawings
FIG. 1 is a NMR chart of Trisphaeridine prepared in example 1 of the present invention;
FIG. 2 is a Trisphaeridine NMR spectrum prepared in example 1.
Detailed Description
In order to make the technical solutions of the present invention better understood, the present invention is further described in detail below with reference to the accompanying drawings.
Example 1
A simple synthesis method of Trisphaeridine (reaction scale is milligram level) comprises the following specific steps:
1) Preparation of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (Compound 3):
6-bromo-3, 4-methylenedioxybenzaldehyde (458.0mg, 2.0mmol) and phenylboronic acid (244.0mg, 2.0mmol) were weighed and added into a 20mL three-necked reaction flask, and 6mL of DMF/H was added 2 O mixture (volume ratio DMF: H) 2 O = 2) 2 CO 3 (276.0 mg,2.0 mmol) was added to the reaction solution, and the reaction solution was stirred at room temperature for 2 to 5 minutes, followed by addition of N 2 Purge for 5 minutes at N 2 Pd (OAc) under atmosphere 2 (22.5mg, 0.1mmol), adding into the reaction solution, sealing, reacting at 25 deg.C for 4 hr, monitoring reaction condition by Thin Layer Chromatography (TLC), adding 48mL water to quench after aldehyde raw material has reacted completely, extracting the mixed solution with ethyl acetate (3 × 20 mL), washing the collected ethyl acetate layer with saturated NaCl solution to remove water, and using anhydrous Na 2 SO 4 Drying, filtering, collecting filtrate, and removing solvent by rotary evaporation instrument to obtain crude product, and separating and purifying the crude product by column chromatography to obtain 380.5mg6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3) as a white solid in 84.1% yield, eluting with Petroleum Ether (PE)/Ethyl Acetate (EA) with a polarity of 20;
2) Preparing Trisphaeridine:
weighing 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (compound 3) (45.2mg, 0.2mmol) and ammonium formate (126.1mg, 2.0mmol), adding the mixture into a dry photoreaction bottle, adding 2mL of HFIP, stirring, dissolving, sealing, placing the obtained solution at room temperature under a 20W purple LED lamp (400-420 nm) for 12 hours at 25 ℃, monitoring the reaction condition by using Thin Layer Chromatography (TLC), stopping the reaction after the reaction is completed, distilling off the solvent by using a rotary evaporator to obtain a crude product, separating the crude product by using column chromatography to obtain 23.2mg of yellow solid Trisphaeridine, wherein the yield is 52%, an eluent is Petroleum Ether (PE)/Ethyl Acetate (EA), and the polarity is 8.
Characterization data for Trisphaeridine compounds prepared in this example:
1 H NMR(500MHz,CDCl 3 )δ9.10(s,1H),8.38(dd,J＝8.2,1.5Hz,1H),8.15(dd,J＝8.3,1.5Hz,1H),7.92(s,1H),7.69(ddd,J＝8.3,7.0,1.5Hz,1H),7.63(ddd,J＝8.2,7.0,1.4Hz,1H),7.35(s,1H),6.18(s,2H).
13 C NMR(126MHz,CDCl 3 )δ151.82,151.51,148.23,144.14,130.28,130.07,128.03,126.71,124.30,123.11,122.02,105.53,101.94,99.98.
the nmr hydrogen spectrum and nmr carbon spectrum of Trisphaeridine prepared in this example are shown in fig. 1 and 2.
Example 2
A simple synthesis method of Trisphaeridine (reaction scale is milligram level) comprises the following specific steps:
1) Preparation of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (Compound 3):
6-bromo-3, 4-methylenedioxybenzaldehyde (458.0mg, 2.0mmol) and phenylboronic acid (341.4mg, 2.8mmol) were weighed and added into a 20mL three-necked reaction flask, and 4mL of DMF/H was added 2 O mixture (volume ratio DMF: H) 2 O = 2) 2 CO 3 (386.4 mg,2.8 mmol) was added to the reaction solution, and the reaction solution was stirred at room temperature for 3 minutes, followed by addition of N 2 Purge for 5 minutes at N 2 Pd (OAc) under atmosphere 2 (27.0 mg, 0.12mmol) was added to the reaction mixture, the mixture was sealed and reacted at 25 ℃ for 4 hours, and thin layer chromatography (T)LC) monitoring the reaction condition, adding 48mL water to quench after the aldehyde raw material is basically completely reacted, extracting the mixed solution with ethyl acetate (3X 20 mL), washing the collected ethyl acetate layer with saturated NaCl solution to remove water, and using anhydrous Na 2 SO 4 Drying, filtering, collecting filtrate, and removing solvent by rotary evaporation instrument to obtain crude product, and separating and purifying by column chromatography to obtain 316.4mg 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3) as a white solid in 70.1% yield, eluting with Petroleum Ether (PE)/Ethyl Acetate (EA) with a polarity of 20;
2) Preparation of Trisphaeridine:
weighing 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (compound 3) (45.2mg, 0.2mmol) and ammonium formate (210.0mg, 1.2mmol), adding the mixture into a dry photoreaction bottle, adding 4mL of HFIP, stirring, dissolving, sealing, placing the obtained solution at room temperature under a 20W purple LED lamp (400-420 nm) at 25 ℃ for 12 hours, monitoring the reaction condition by using Thin Layer Chromatography (TLC), stopping the reaction after the reaction is completed, distilling off the solvent by using a rotary evaporator to obtain a crude product, separating the crude product by using column chromatography to obtain 17.4mg of yellow solid Trisphaeridine, wherein the yield is 39%, an eluent is Petroleum Ether (PE)/Ethyl Acetate (EA), and the polarity is 8.
Example 3
A simple synthesis method of Trisphaeridine (reaction scale is milligram level) comprises the following specific steps:
1) Preparation of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (Compound 3):
6-bromo-3, 4-methylenedioxybenzaldehyde (458.0mg, 2.0mmol) and phenylboronic acid (219.4mg, 1.8mmol) were weighed and added into a 20mL three-necked reaction flask, and 10mL of DMF/H was added 2 O mixture (volume ratio DMF: H) 2 O = 2) 2 CO 3 (248.7mg, 1.8mmol) was added to the reaction solution, and the reaction solution was stirred at room temperature for 3 minutes, followed by addition of N 2 Purge for 5 minutes at N 2 Pd (OAc) under atmosphere 2 (4.5 mg, 0.02mmol) in a reaction solution, sealing, reacting at 25 ℃ for 4 hours, and usingMonitoring the reaction by Thin Layer Chromatography (TLC), adding 48mL water to quench after the aldehyde raw material is basically reacted completely, extracting the mixed solution with ethyl acetate (3X 20 mL), washing the collected ethyl acetate layer with saturated NaCl solution to remove water, and removing water with anhydrous Na 2 SO 4 Drying, filtering, collecting filtrate, and removing solvent by rotary evaporation instrument to obtain crude product, which is separated and purified by column chromatography to obtain 339.4mg 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3) as a white solid in 75.1% yield, using an eluent of Petroleum Ether (PE)/Ethyl Acetate (EA) with a polarity of 20;
2) Preparing Trisphaeridine:
weighing 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (compound 3) (45.2mg, 0.2mmol) and ammonium formate (138.8mg, 2.2mmol), adding into a dry photoreaction bottle, adding 0.7mL of HFIP, stirring for dissolving, sealing, placing the obtained solution at room temperature under a 20W purple LED lamp (400-420 nm) for reacting at 25 ℃ for 12 hours, monitoring the reaction condition by using Thin Layer Chromatography (TLC), stopping the reaction after the reaction is completed, distilling off the solvent by using a rotary evaporator to obtain a crude product, separating the crude product by using column chromatography to obtain 19.1mg of yellow solid Trisphaeridine with the yield of 42.9%, using an eluent of Petroleum Ether (PE)/Ethyl Acetate (EA), and having the polarity of 8.
Example 4
A simple synthesis method of Trisphaeridine (the reaction scale is gram level) comprises the following specific steps:
1) Preparation of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde (Compound 3):
6-bromo-3, 4-methylenedioxybenzaldehyde (1832.0mg, 8.0mmol) and phenylboronic acid (9760mg, 8.0mmol) were weighed and added to a 50mL three-necked reaction flask, and 24mL of DMF/H was added 2 O mixture (volume ratio DMF: H) 2 O = 2), adding clean magnetons, stirring to dissolve, and weighing K 2 CO 3 (1104.0 mg,8.0 mmol) was added to the reaction solution, and the reaction solution was stirred at room temperature for 2 to 5 minutes, followed by addition of N 2 Purge for 5 minutes at N 2 Pd (OAc) under atmosphere 2 (89.8 mg,0.4 mmol) was added to the reaction mixture, followed by sealingReacting at 25 deg.C for 4 hr, monitoring reaction condition by Thin Layer Chromatography (TLC), adding 190mL water to quench after aldehyde raw material is basically reacted completely, extracting the mixed solution with ethyl acetate (3 × 80 mL), washing the collected ethyl acetate layer with saturated NaCl solution to remove water, and adding anhydrous Na 2 SO 4 Drying, filtering, collecting filtrate, and removing solvent by rotary evaporation instrument to obtain crude product, which is separated and purified by column chromatography to obtain 1517.1mg 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde (compound 3) as a white solid in 83.9% yield, eluting with Petroleum Ether (PE)/Ethyl Acetate (EA) with a polarity of 20;
2) Preparing Trisphaeridine:
weighing 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde (compound 3) (1131.2mg, 5.0 mmol) and ammonium formate (3150mg, 50.0 mmol), adding into a dry photoreaction bottle, adding 50mL of HFIP, stirring for dissolving, sealing, placing the obtained solution at room temperature under a 20W purple LED lamp (400-420 nm) for 12 hours at 25 ℃, monitoring the reaction condition by using Thin Layer Chromatography (TLC), stopping the reaction after the reaction is completed, distilling off the solvent by using a rotary evaporator to obtain a crude product, separating the crude product by using column chromatography to obtain 613.4mg of yellow solid Trisphaeridine with the yield of 55%, using an eluent of Petroleum Ether (PE)/Ethyl Acetate (EA) and the polarity of 8.
From the above examples, it can be seen that the yield of the reaction is higher when the reaction conditions for each reaction are within the listed ranges than when they are outside the listed ranges, the yield is not adversely affected in gram-scale reactions, and the improvement is achieved, and it can be used for the mass production of Trisphaeridine compounds on gram-scale.
While the foregoing is directed to the preferred embodiment of the present invention, it will be apparent to those skilled in the art that various changes in the form and details of the solvents, catalysts, and reactants used in the reaction may be made without departing from the spirit of the invention and these changes are intended to be within the scope of the invention.
Claims (10)
1. A simple synthesis method of Trisphaeridine is characterized by comprising the following specific steps:
s1, dissolving 6-bromo-3, 4-methylene dioxybenzaldehyde and phenylboronic acid in a solvent, and adding K 2 CO 3 After stirring evenly, N is introduced 2 In N at 2 Adding Pd (OAc) under atmosphere 2 Performing Suzuki coupling reaction, washing the reaction solution after the reaction is finished, extracting with ethyl acetate, collecting the organic phase, drying, concentrating, and purifying by column chromatography to obtain 6-phenylbenzo [ d ]][1,3]Dioxolane-5-carbaldehyde;
s2, adding the 6-phenylbenzo [ d ] [1,3] dioxolane-5-formaldehyde obtained in the step S1 and ammonium formate into a photoreaction bottle, then adding 1, 3-hexafluoro-2-propanol, stirring and dissolving, then carrying out 6 pi electrocyclic reaction under the irradiation of visible light, concentrating the reaction solution after the reaction is finished, and purifying by column chromatography to obtain Trisphaeridine.
2. The simplified synthesis method of Trisphaeridine according to claim 1, wherein the molar ratio of 6-bromo-3, 4-methylenedioxybenzaldehyde to phenylboronic acid in S1 is 1:0.9 to 1.4.
3. The simple synthesis method of Trisphaeridine according to claim 1, wherein the solvent S1 is a mixture of N, N-Dimethylformamide (DMF) and water, and the volume ratio of the DMF to the water is 2-3: 1, the concentration of the 6-bromo-3, 4-methylenedioxybenzaldehyde in the solvent is 0.2-0.5 mol/L.
4. The method for the facile synthesis of Trisphaeridine of claim 1, wherein S1 said K 2 CO 3 The molar ratio of the 6-bromo-3, 4-methylenedioxybenzaldehyde to the compound is 1:0.9 to 1.4.
5. The simplified synthesis method of Trisphaeridine according to claim 1, wherein the Suzuki coupling reaction conditions of S1 are as follows: reacting for 3-5 hours at 20-30 ℃.
6. The simplifications of Trisphaeridine according to claim 1A synthetic method, wherein S1 represents Pd (OAc) 2 The mol ratio of the compound to 6-bromo-3, 4-methylene dioxybenzaldehyde is 0.01-0.06: 1.
7. the simplified synthesis method of Trisphaeridine according to claim 1, wherein the molar ratio of 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde to ammonium formate in S2 is 1:6 to 11.
8. The simplified process for the synthesis of Trisphaeridine according to claim 1, wherein the concentration of S2 said 6-phenylbenzo [ d ] [1,3] dioxolane-5-carbaldehyde in 1, 3-hexafluoro-2-propanol is 0.05 to 0.3mol/L.
9. The simple synthesis method of Trisphaeridine according to claim 1, wherein the visible light source of S2 is a purple LED lamp, the power is 3-20W, and the wavelength is 400-420 nm.
10. The simple synthesis method of Trisphaeridine according to claim 1, wherein the 6 pi electrocyclization reaction conditions of S2 are as follows: reacting for 10-12 hours at 20-35 ℃.
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| CN105153172A (en) * | 2015-10-13 | 2015-12-16 | 遵义医学院 | Synthesis method of trisphaeridine |
| CN114232013A (en) * | 2021-11-12 | 2022-03-25 | 华南理工大学 | Method for synthesizing indoloquinoline compound under electrochemical condition |
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| CN105153172A (en) * | 2015-10-13 | 2015-12-16 | 遵义医学院 | Synthesis method of trisphaeridine |
| CN114232013A (en) * | 2021-11-12 | 2022-03-25 | 华南理工大学 | Method for synthesizing indoloquinoline compound under electrochemical condition |
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