CN115819436A - Process for producing quinolino-sulfolane derivative - Google Patents
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Abstract
The invention discloses a preparation method of a quinosulfolane derivative, which comprises the steps of mixing 2- (N-phenyl propynyl-N-sulfonyl) aminophenylacetylene, aryl diazonium tetrafluoroborate and 1, 4-diazabicyclo [2.2.2]]Octane and Sulfur dioxide Complex (DABCO.2SO) 2 ) 1, 4-diazabicyclo [2.2.2]And putting octane and a solvent into a reactor, removing the solvent after the reaction is finished, washing the obtained mixture with water, and extracting, drying and carrying out column chromatography separation to obtain a pure product of the quinoline sulfolane derivative. The process flow is simple, the efficient construction of the pyridine ring and the sulfolane ring can be realized through one-step efficient conversion process, and the synthesis efficiency and the step economy are high. Functional groups such as nitro, chlorine, fluorine and the like in the target product of the preparation method can be subjected to further conversion and functionalization reaction, so that the target product can be conveniently subjected to diversified structural modification, and the preparation method has good antitumor activity.
Description
Technical Field
The invention relates to the technical field of organic compound synthesis, in particular to a preparation method of a quinoline sulfolane derivative.
Background
Quinolines are an important class of nitrogen-containing organic heterocyclic compounds with a broad spectrum of physiological and pharmacological activities (Journal of physiological chemistry,2007,50,21, journal of physiological chemistry,2005,48, 2243). The cyclic sulfones compounds are important sulfur-containing Organic heterocyclic compounds and have important biological activity (Organic & Biomolecular Chemistry,2017,15, 5000). Quinolinosulfulfones are important nitrogen-containing and sulfur-containing Organic heterocyclic compounds, and have important biological activities such as adenine ribonucleotide phosphodiesterase inhibitory activity (The Journal of Organic Chemistry,1979,44, 2977).
A preparation method of a quinosulfolane derivative is reported in the literature: the method adopts a palladium catalyst, and under the action of the palladium catalyst, substituted aminophenylboronic acid and substituted thiophene derivatives undergo coupling reaction and intramolecular cyclization reaction to generate quinothiophene derivatives; the generated quinophthalone derivative generates the quinosulfolane derivative under the action of a subsequent oxidant m-chloroperoxybenzoic acid.
The method needs to be carried out step by step, and the operation is relatively complicated; the raw material is substituted for thiophene derivative, which is not easy to obtain; the palladium complex used in the reaction is an expensive catalyst and is difficult to recover; meanwhile, m-chloroperoxybenzoic acid is used as an oxidant in the method, and certain potential safety hazards exist in the operation.
Therefore, the method for synthesizing the compound by developing a simple, convenient and efficient method has very important significance for the development and research of new drugs and new materials.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention aims to provide a preparation method of a quinoline sulfolane derivative, which has a simple process flow and high conversion efficiency.
A process for producing a quinosulfolane derivative, characterized by comprising: putting 2- (N-phenyl propynyl-N-sulfonyl) aminophenylacetylene, aryltetrafluoroborate diazonium salt, 1, 4-diazabicyclo [2.2.2] octane, sulfur dioxide complex (DABCO.2SO 2), 1, 4-diazabicyclo [2.2.2] octane and a solvent into a reactor, and reacting at 50 ℃; and after the reaction is finished, removing the solvent, washing the obtained mixture with water, and performing extraction, drying and column chromatography separation to obtain a pure product of the quinoline sulfolane derivative.
Preferably, the solvent is one of 1, 2-dichloroethane, methanol, ethanol, isopropanol and chloroform.
Preferably, the aryl tetrafluoroborate diazonium salt is selected from one of 4-methylphenyl tetrafluoroborate diazonium salt, 3-methylphenyl tetrafluoroborate diazonium salt, 2-methylphenyl tetrafluoroborate diazonium salt, 4-chlorophenyl tetrafluoroborate diazonium salt, 4-nitrophenyltetrafluoroborate diazonium salt and 4-fluorophenyl tetrafluoroborate diazonium salt.
Preferably, the 2- (N-phenylpropynyl-N-sulfonyl) aminophenylacetylene, aryltetrafluoroborate diazonium salt, 1, 4-diazabicyclo [2.2.2]Octane and Sulfur dioxide Complex (DABCO.2SO) 2 ) 1, 4-diazabicyclo [2.2.2]The molar ratio between the octanes was 1.0:1.0-3.0:2.0-4.0:0.25-0.75.
Preferably, the reaction time is 2 hours.
The technical scheme has the following beneficial effects: the process flow is simple, the efficient construction of the pyridine ring and the sulfolane ring can be realized through one-step efficient conversion process, and the synthesis efficiency and the step economy are high. Functional groups such as nitro, chlorine, fluorine and the like in the target product of the preparation method can be subjected to further conversion and functionalization reaction, so that the target product can be conveniently subjected to diversified structural modification, and the preparation method has good antitumor activity.
Drawings
FIG. 1 is a NMR chart of a target compound of example 1 of the present invention.
FIG. 2 shows the NMR spectrum of the target compound of example 2 of the present invention.
FIG. 3 is a NMR spectrum of a target compound of example 3 of the present invention.
FIG. 4 is a NMR chart of a target compound of example 4 of the present invention.
FIG. 5 shows the NMR spectrum of the target compound of example 5 of the present invention.
FIG. 6 is a NMR chart of a target compound of example 6 of the present invention.
FIG. 7 is a graph showing a comparison of the inhibition of Ketr-3 cytotoxicity by the target compound of example 6 of the present invention.
Detailed Description
The following description of the embodiments of the present invention is provided for illustrative purposes, and other advantages and effects of the present invention will become apparent to those skilled in the art from the present disclosure.
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of example embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to provide a thorough understanding of embodiments of the invention. One skilled in the relevant art will recognize, however, that the invention may be practiced without one or more of the specific details, or with other methods, components, devices, steps, and so forth. In other instances, well-known technical solutions have not been shown or described in detail to avoid obscuring aspects of the invention.
Example 1: a preparation method of a quinoline sulfolane derivative I.
2- (N-phenylpropynyl-N-sulfonyl) aminophenylacetylene (0.2 mmol), 4-methylphenyltetrafluoroborate diazonium salt (0.2-0.6 mmol) and 1, 4-diazabicyclo [2.2.2] are added to a reaction tube]Octane and sulfur dioxide complex, i.e. DABCO.2SO 2 (DABSO) (0.4-0.8 mmol), 1, 4-diazabicyclo [2.2.2]Octane (DABCO) (0.05-0.15 mmol) and 2mL of 1, 2-dichloroethane are reacted at 50 ℃ under the protection of argon 2And (4) hours.
And after the reaction is finished, removing the solvent, washing the obtained mixture with water, and performing extraction, drying and column chromatography separation to obtain a pure product of the quinoline sulfolane derivative I:2, 2-dioxo-1, 5-bis (4-tosyl) -3-phenyl-4, 5-dihydrothieno [3,4-c ] quinoline, of the formula:
yield: 55 percent; a yellow solid;
as shown in FIG. 1, the target compound showed a hydrogen nuclear magnetic resonance spectrum (CDCl 3,400 MHz) (delta, ppm): 8.32 (d, J =8.0Hz, 1H), 7.97 (d, J =8.4Hz, 2H), 7.81 (d, J =8.0Hz, 1H), 7.70-7.65 (m, 1H), 7.57-7.39 (m, 8H), 7.05 (s, 4H), 4.63 (s, 2H), 2.48 (s, 3H), 2.45 (s, 3H).
The target compound of the quinoline sulfolane compound can be used for inhibiting the activity of tumor cell growth.
Example 2: a process for producing a quinolinosulfone derivative II.
2- (N-phenylpropynyl-N-sulfonyl) aminophenylacetylene (0.2 mmol), 3-methylphenyltetrafluoroboric acid diazonium salt (0.2-0.6 mmol), and 1, 4-diazabicyclo [2.2.2] in a reaction tube]Octane and sulfur dioxide complex, i.e. DABCO.2SO 2 (DABSO) (0.4-0.8 mmol), 1, 4-diazabicyclo [2.2.2]Octane (DABCO) (0.05-0.15 mmol) and 2mL of 1, 2-dichloroethane were reacted at 50 ℃ for 2 hours under protection of argon.
And after the reaction is finished, removing the solvent, washing the obtained mixture with water, and performing extraction, drying and column chromatography separation to obtain a pure product of the quinoline sulfolane derivative II:2, 2-dioxo-1- (3-methylbenzenesulfonyl) -3-phenyl-5- (4-toluenesulfonyl) -4, 5-dihydrothieno [3,4-c ] quinoline, having the following structural formula:
yield: 68 percent; a yellow solid;
as shown in FIG. 2, the nuclear magnetic resonance hydrogen spectrum (CDCl3, 400MHz) (delta, ppm) of the target compound was 8.28 (d, J =7.6Hz, 1H), 7.94 (s, 1H), 7.87 (d, J =8.0Hz, 1H), 7.80 (d, J =8.0Hz, 1H), 7.67 (d, J =8.4Hz, 1H), 7.59-7.41 (m, 9H), 7.03 (d, J =2.4Hz, 4H), 4.62 (s, 2H), 2.46 (s, 3H), 2.43 (s, 3H).
The target compound of the quinoline sulfolane compound can be used for inhibiting the activity of tumor cell growth.
Example 3: a preparation method of a quinoline sulfolane derivative III.
2- (N-phenylpropynyl-N-sulfonyl) aminophenylacetylene (0.2 mmol), 2-methylphenyltetrafluoroboric acid diazonium salt (0.2-0.6 mmol), and 1, 4-diazabicyclo [2.2.2] in a reaction tube]Octane and sulfur dioxide complex, i.e. DABCO.2SO 2 (DABSO) (0.4-0.8 mmol), 1, 4-diazabicyclo [2.2.2]Octane (DABCO) (0.05-0.15 mmol) and 2mL of 1, 2-dichloroethane were reacted at 50 ℃ for 2 hours under protection of argon.
And after the reaction is finished, removing the solvent, washing the obtained mixture with water, and performing extraction, drying and column chromatography separation to obtain a pure product of the quinoline sulfolane derivative III:2, 2-dioxo-1- (2-methylbenzenesulfonyl) -3-phenyl-5- (4-toluenesulfonyl) -4, 5-dihydrothieno [3,4-c ] quinoline, having the following structural formula:
yield: 84%; a yellow solid;
as shown in FIG. 3, the nuclear magnetic resonance hydrogen spectrum (CDCl3, 400MHz) (delta, ppm) of the target compound was 8.32 (d, J =8.0Hz, 1H), 8.01 (d, J =8.0Hz, 1H), 7.83 (d, J =7.6Hz, 1H), 7.66 (d, J =8.0Hz, 1H), 7.59 (d, J =7.2Hz, 1H), 7.57-7.48 (m, 5H), 7.43 (d, J =8.0Hz, 3H), 7.17 (s, 4H), 4.70 (s, 2H), 2.67 (s, 3H), 2.45 (s, 3H).
The target compound of the quinoline sulfolane compound can be used for inhibiting the activity of tumor cell growth.
Example 4: a process for producing a quinolinesulfonane derivative IV.
Adding 0.2mmol of 2- (N-phenyl propynyl-N-sulfonyl) aminophenylacetylene into a reaction tube,4-chlorophenyl Tetrafluoroboronic acid diazonium salt (0.2-0.6 mmol), 1, 4-diazabicyclo [2.2.2]Octane and sulfur dioxide complex, i.e. DABCO.2SO 2 (DABSO) (0.4-0.8 mmol), 1, 4-diazabicyclo [2.2.2]Octane (DABCO) (0.05-0.15 mmol) and 2mL of 1, 2-dichloroethane were reacted at 50 ℃ for 2 hours under protection of argon.
And after the reaction is finished, removing the solvent, washing the obtained mixture with water, and performing extraction, drying and column chromatography separation to obtain a pure product of the quinoline sulfolane derivative IV:2, 2-dioxo-1- (4-chlorobenzenesulfonyl) -3-phenyl-5- (4-toluenesulfonyl) -4, 5-dihydrothieno [3,4-c ] quinoline, having the following structural formula:
yield: 64 percent; a yellow solid;
as shown in FIG. 4, the nuclear magnetic resonance hydrogen spectrum (CDCl3, 400MHz) (delta, ppm) of the target compound was 8.22 (d, J =8.4Hz, 1H), 8.02 (d, J =8.8Hz, 2H), 7.83 (d, J =8.0Hz, 1H), 7.69 (d, J =7.6Hz, 1H), 7.57 (d, J =8.4Hz, 5H), 7.47 (d, J =8.4Hz, 3H), 7.08 (s, 4H), 4.66 (s, 2H), 2.44 (s, 3H).
The target compound of the quinoline sulfolane compound can be used for inhibiting the activity of tumor cell growth.
Example 5: a process for producing a quinonesulfolane derivative V.
2- (N-phenylpropynyl-N-sulfonyl) aminophenylacetylene (0.2 mmol), 4-nitrophenyltetrafluoroborate diazonium salt (0.2-0.6 mmol) and 1, 4-diazabicyclo [2.2.2] are added to a reaction tube]Octane and sulfur dioxide complex, i.e. DABCO.2SO 2 (DABSO) (0.4-0.8 mmol), 1, 4-diazabicyclo [2.2.2]Octane (DABCO) (0.05-0.15 mmol) and 2mL of 1, 2-dichloroethane were reacted at 50 ℃ for 2 hours under protection of argon.
And (3) after the reaction is finished, removing the solvent, washing the obtained mixture with water, and performing extraction, drying and column chromatography separation to obtain a pure product of the quinoline sulfolane derivative V:2, 2-dioxo-1- (4-nitrobenzenesulfonyl) -3-phenyl-5- (4-toluenesulfonyl) -4, 5-dihydro [3,4-c ] quinoline, having the following structural formula:
yield: 55 percent; a yellow solid;
as shown in FIG. 5, the nuclear magnetic resonance hydrogen spectrum (CDCl3, 400MHz) (delta, ppm) of the target compound was 8.43 (d, J =8.8Hz, 2H), 8.30 (d, J =8.8Hz, 2H), 8.06 (d, J =8.0Hz, 1H), 7.83 (d, J =8.0Hz, 1H), 7.71 (d, J =8.4Hz, 1H), 7.61-7.43 (m, 6H), 7.19-7.07 (m, 4H), 4.68 (s, 2H), 2.46 (s, 3H).
The target compound of the quinoline sulfolane compound can be used for inhibiting the activity of tumor cell growth.
Example 6: a preparation method of a quinoline sulfolane derivative VI.
2- (N-phenylpropynyl-N-sulfonyl) aminophenylacetylene (0.2 mmol), 4-fluorophenyltetrafluoroboric acid diazonium salt (0.2-0.6 mmol), and 1, 4-diazabicyclo [2.2.2] are added to a reaction tube]Octane and sulfur dioxide complex, i.e. DABCO.2SO 2 (DABSO) (0.4-0.8 mmol), 1, 4-diazabicyclo [2.2.2]Octane (DABCO) (0.05-0.15 mmol) and 2mL of 1, 2-dichloroethane were reacted at 50 ℃ for 2 hours under protection of argon.
And 2) after the reaction is finished, removing the solvent, washing the obtained mixture with water, and performing extraction, drying and column chromatography separation to obtain a pure product of the quinoline sulfolane derivative VI:2, 2-dioxo-1- (4-fluorobenzenesulfonyl) -3-phenyl-5- (4-toluenesulfonyl) -4, 5-dihydrothieno [3,4-c ] quinoline having the following structural formula:
yield: 60 percent; a yellow solid;
as shown in FIG. 5, the nuclear magnetic resonance hydrogen spectrum (CDCl3, 400MHz) (delta, ppm) of the target compound was 8.27 (d, J =8.0Hz, 1H), 8.11 (d, J =5.2Hz, 2H), 7.83 (d, J =8.4Hz, 1H), 7.69 (d, J =8.0Hz, 1H), 7.61-7.51 (m, 3H), 7.48 (d, J =8.0Hz, 3H), 7.30 (d, J =8.4Hz, 2H), 7.10 (s, 4H), 4.65 (s, 2H), 2.45 (s, 3H).
The target compound of the quinoline sulfolane compound can be used for inhibiting the activity of tumor cell growth. The growth inhibitory activity of Compound VI of interest of this example on human renal carcinoma cells Ketr-3 was determined by the CCK8 method. The target compound VI is diluted by dimethyl sulfoxide into three concentrations of 1, 10 and 100ng/mL, and after 24 hours of action, the cytotoxicity of the target compound VI on Ketr-3 is respectively determined. As a result, as shown in FIG. 7, the inhibition rate of Ketr-3 in human renal cancer cells was 9.48% at a concentration of 1 ng/mL; when the concentration is 10ng/mL, the inhibition rate of human renal cancer cell Ketr-3 is 9.26%; and at a concentration of 100ng/mL, the inhibition rate of Ketr-3 of human renal cancer cells is 23.40%.
The research results show that the quinoline sulfolane compounds such as the target compound and the like in the patent embodiment have good activity of inhibiting the growth of tumor cells, and have important guiding significance and application prospect for finding novel efficient antitumor drugs.
The process flow is simple, the efficient construction of the pyridine ring and the sulfolane ring can be realized through one-step efficient conversion process, and the synthesis efficiency and the step economy are high. Functional groups such as nitro, chlorine, fluorine and the like in the target product of the preparation method can be subjected to further conversion and functionalization reaction, so that the target product can be conveniently subjected to diversified structural modification, and the preparation method has good antitumor activity.
The foregoing embodiments are merely illustrative of the principles and utilities of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or change the above-mentioned embodiments without departing from the spirit and scope of the present invention. Accordingly, it is intended that all equivalent modifications or changes which can be made by those skilled in the art without departing from the spirit and technical spirit of the present invention be covered by the claims of the present invention.
Claims (6)
1. A method for producing a quinosulfolane derivative, comprising the steps of:
2- (N-phenyl propynyl-N-sulfonyl) aminophenylacetylene, aryltetrafluoroborate diazonium salt, 1, 4-diazabicyclo [2.2.2]Octane and Sulfur dioxide Complex (DABCO.2SO) 2 ) 1, 4-diazabicyclo [2.2.2]Putting octane and a solvent into a reactor for reaction; and after the reaction is finished, removing the solvent, washing the obtained mixture with water, and performing extraction, drying and column chromatography separation to obtain a pure product of the quinoline sulfolane derivative.
2. The process for producing a quinolinesulfonane derivative according to claim 1, wherein: the solvent is one of 1, 2-dichloroethane, methanol, ethanol, isopropanol and chloroform.
3. The process for producing a quinolinosulfone derivative according to claim 1, wherein: the aryl tetrafluoroborate diazonium salt is selected from one of 4-methylphenyl tetrafluoroborate diazonium salt, 3-methylphenyl tetrafluoroborate diazonium salt, 2-methylphenyl tetrafluoroborate diazonium salt, 4-chlorophenyl tetrafluoroborate diazonium salt, 4-nitrophenyltetrafluoroborate diazonium salt and 4-fluorophenyl tetrafluoroborate diazonium salt.
4. The process for producing a quinolinosulfone derivative according to claim 1, wherein: the 2- (N-phenylpropynyl-N-sulfonyl) aminophenylacetylene, aryltetrafluoroborate diazonium salt, 1, 4-diazabicyclo [2.2.2]Octane and Sulfur dioxide Complex (DABCO.2SO) 2 ) 1, 4-diazabicyclo [2.2.2]The molar ratio between the octanes was 1.0:1.0-3.0:2.0-4.0:0.25-0.75.
5. The process for producing a quinolinosulfone derivative according to claim 1, wherein: the reaction time was 2 hours.
6. The process for producing a quinolinosulfone derivative according to claim 1, wherein: the reaction temperature was 50 ℃.
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| WO1999015529A1 (en) * | 1997-09-23 | 1999-04-01 | Novo Nordisk A/S | MODULES OF PROTEIN TYROSINE PHOSPHATASES (PTPases) |
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