CN115403635A - C-H sulphonation reaction of DNA (deoxyribonucleic acid) coding aromatic compound - Google Patents
C-H sulphonation reaction of DNA (deoxyribonucleic acid) coding aromatic compound Download PDFInfo
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- C40B50/14—Solid phase synthesis, i.e. wherein one or more library building blocks are bound to a solid support during library creation; Particular methods of cleavage from the solid support
- C40B50/16—Solid phase synthesis, i.e. wherein one or more library building blocks are bound to a solid support during library creation; Particular methods of cleavage from the solid support involving encoding steps
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Abstract
A C-H sulphonation reaction of DNA coding aromatic hydrocarbon compound. The present patent provides a method for synthesizing DNA-encoding compounds based on a photo-promoted, ion-pair complex electron transfer, free radical coupling reaction. The method adopts DNA coding sulfonium salt activated arene as an electron acceptor, sodium sulfinate as an electron donor, and adds alkali into an organic solvent to complete a diradical coupling reaction under the promotion of certain wavelength light so as to synthesize the DNA coding sulfone compound. The method has the advantages of no transition metal photocatalyst, mild conditions, convenient operation, good substrate universality and high product yield, greatly expands the structure type and the drug-like property of the DNA coding compound by the participation of the bioactive compound, provides a research basis for the construction and the later structural modification of a DNA coding bioactive compound library, and has important industrial application prospects.
Description
Technical Field
The invention belongs to the field of organic synthesis and pharmaceutical chemistry, and particularly relates to a method for synthesizing a DNA (deoxyribonucleic acid) coding sulfone compound based on ion-pair compound electron transfer free radical coupling reaction.
Background
Late structural modification (late functionalization) of biologically active compounds is of crucial importance in drug development. The strategy can directly carry out structure diversification modification on the bioactive molecules, avoid de novo synthesis and quickly obtain a target product. Transition metal catalyzed C-H functionalization at specific sites is the main means for late structural modification of currently bioactive compounds, and has been implemented to introduce functional groups (such as fluorine, cyano, amine or short-chain alkane) with small volume into complex molecules. However, the currently developed late-stage structure modification method basically adopts a transition metal catalyst, and the application of the late-stage structure modification method in the pharmaceutical field is influenced by the problem of metal residue. In 2019, the Ritter group reported a method of site-selective aromatic C-H functionalization that did not require a directing group or a pre-activated functional group (Nature 2019, 567, 223-228). The reaction is carried out by forming more stable sulfonium salt, thereby further completing subsequent multiple chemical transformations and preparing the later-stage structure modified product of the bioactive compound.
By using the relative stability and detectability of DNA, professor Sydney Brenner and Richard Lerner of Scripps research in the United states of America put forward the concept of DNA coding compound libraries, the technology enables each compound to be connected with a specific DNA fragment on a molecular level to record the structure-related information of the compound, and the structure of an active compound can be rapidly determined in the screening of a lead compound. The concept of libraries of DNA-encoding compounds has been proposed, and great progress has been made in both library construction strategies and target screening. The development of DNA compatible chemistry remains a bottleneck that limits this technology. How to improve the diversity of compound structures is also an urgent problem to be solved by DEL technology.
The invention aims to provide a method for synthesizing a DNA (deoxyribonucleic acid) coding sulfone compound based on an ion pair compound electron transfer free radical coupling reaction. The method adopts DNA coding sulfonium salt activated aromatic hydrocarbon as an electron acceptor, sodium sulfinate as an electron donor, adds alkali into an organic solvent, and generates a diradical coupling reaction under the promotion of certain wavelength light to complete the synthesis of the DNA coding sulfone compound. The method has the advantages of no transition metal photocatalyst, mild conditions, convenient operation, good substrate universality and high product yield, greatly expands the structure type and the drug-like property of the DNA coding compound by the participation of the bioactive compound, provides a research basis for the construction and the later structural modification of a DNA coding bioactive compound library, and has important industrial application prospects.
Disclosure of Invention
The invention aims to provide a synthesis method of a DNA coding sulfone compound based on ion-pair complex electron transfer free radical reaction, which is promoted by light and is shown in the formula (I), and is characterized in that:
1) Immobilizing a DNA-encoded sulfonium salt compound having the structure of formula (II) on a resin, and washing with an organic solvent;
2) Adding the immobilized DNA coding sulfonium salt compound with the structure of formula (II), sodium sulfinate with the structure of formula (III) and alkali into an organic solvent, reacting for 2-24 hours at 0-80 ℃ under the irradiation of light with a certain wavelength, removing the reaction solvent, and washing for multiple times;
3) Adding an Elute buffer to Elute the DNA coding sulfone compound with the structure of formula (I), precipitating and centrifuging the product to obtain the DNA coding sulfone compound with the structure of formula (I).
Wherein:
the DNA coding sulfonium salt compound with the structure of formula (II) is a DNA coding compound obtained by connecting an amine compound containing a DNA sequence with a sulfonium salt containing a carboxyl group through an amide bond;
the DNA is a double-stranded nucleotide sequence obtained by polymerizing artificially modified/unmodified nucleotide monomers.
Ar group in the sulfonium salt shown in the formula (II) is aryl, substituted aryl, heteroaryl and substituted heteroaryl; the aromatic ring in the aryl and heteroaryl is selected from benzene, naphthalene, furan, thiophene, pyrrole, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrimidine, indole, quinoline, diazine and triazine; the substituted aryl or substituted heteroaryl group can be a mono-substituted aryl or heteroaryl group or a poly-substituted aryl or heteroaryl group; the substituent is selected from methyl, ethyl and C 3 ～C 6 Alkyl radical, C 3 ～C 6 Cycloalkyl, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, nitrile, aldehyde, acetyl, alkyl ketone, ester, amide, methoxy, amine, hydroxyl, mercapto, alkenyl, alkynePhenyl, phenyl; the Ar group can be a natural product or a medicament containing the functional group;
in the sulfonium salt shown in the formula (II), X group is selected from oxygen, sulfur, nitrogen, selenium and CH 2 、CH 2 -CH 2 Or, it may be a single bond;
the sodium sulfinate R group shown in the formula (III) is selected from aryl, substituted aryl, heteroaryl, substituted heteroaryl and C 1 ～C 6 Alkyl radical, C 3 ～C 6 Cycloalkyl, wherein aryl and heteroaryl are selected from phenyl, naphthyl, indolyl, furyl, thienyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, pyridyl, pyrimidinyl, quinolinyl, diazinyl, triazinyl; the substituted aryl or heteroaryl can be mono-substituted aryl or heteroaryl and can also be poly-substituted aryl or heteroaryl, and the substituent is selected from methyl, ethyl and C 3 ～C 6 Alkyl radical, C 3 ～C 6 Cycloalkyl, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, nitrile, aldehyde, acetyl, alkyl ketone, ester, amide, methoxy, amine, hydroxyl, mercapto, alkenyl, alkynyl and phenyl; the alkyl is methyl, ethyl, benzyl, hydroxymethyl, C 3 ～C 10 Straight chain alkyl group of (1), C 3 ～C 10 Branched alkyl of C 3 ～C 6 Cycloalkyl groups of (a);
the alkali is DBU (1,8-diazabicycloundec-7-ene), DABCO (1,4-diazabicyclo [2.2.2] octane), TMG (tetramethylguanidine), DMAP (4-dimethylaminopyridine), triethylamine, N-diisopropylethylamine, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium fluoride and sodium phosphate; preferably, the base is cesium carbonate.
The organic solvent is one or a mixture of more of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, methanol, ethanol, isopropanol, acetone, 1,4-dioxane, acetonitrile, tetrahydrofuran, toluene, dichloromethane, 1,2-dichloroethane, chloroform and an inorganic salt buffer solution; preferably, the reaction solvent is DMSO.
The molar concentration of the sodium sulfinate is 0.2M, 0.5M, 0.8M, 1.0M and 1.5M; preferably, the molar concentration of sodium sulfinate is 1.0M.
The molar concentration of the alkali is 0.1M, 0.2M, 0.4M, 0.8M, 1.0M and 1.5M; preferably, the molar concentration of the base is 0.4M.
The light with certain wavelength is as follows: 13wCFL light, white light, 365nm light, 390nm light, 427nm light, 455nm light, 530nm light; preferably, the light source is 365nm light.
The reaction temperature is room temperature, 20 ℃, 30 ℃, 40 ℃, 60 ℃ and 80 ℃; preferably, the reaction temperature is room temperature.
The reaction time is 2 hours, 4 hours, 6 hours, 8 hours, 12 hours, 18 hours, 20 hours and 24 hours; preferably, the reaction time is 18 hours.
Detailed Description
The present invention is further illustrated by the following examples, which are not intended to limit the scope of the invention.
Example 1
Step 1: synthesis of DNA-encoded sulfonium salt Compound (II)
Reacting DNA-NH 2 (4. Mu. Mol), DMTMM (1M, 3mL), p-methoxyphenylacetic acid sulfonium salt (1M, 0.4 mL) were added to a borax buffer solution (pH =9.5, 100mM, 3mL), reacted at room temperature for 2h, and after completion of the reaction, ethanol (15 mL) and NaCl solution (5M, 0.4 mL) were added to precipitate DNA. Water, acetonitrile and DIPEA were added to a sample tube containing the obtained precipitate, and the reaction was carried out at 70 ℃ for 12 hours. After the reaction was completed, ethanol (15 mL) and NaCl solution (5M, 0.4 mL) were added to precipitate the DNA-encoding sulfonium salt compound (II-a), and the structure of the compound was determined by LC-MS at a conversion of 74%.
Step 2: free radical coupling reaction of DNA encoding sulfonium salt (II-a) with sodium sulfinate (III-a)
DNA-encoded sulfonium salt compound (II-a, 10 nmol) was immobilized on a resin, washed with DMSO, and DMSO (0.2 mL), sodium p-tolylsulfinate (III-a, 1M), and Cs were added to the resin, respectively 2 CO 3 (0.4M), irradiating by a 365nm light source, reacting for 18h at room temperature, removing a reaction solvent after the reaction is finished, washing for multiple times, finally adding Elutebauffer (0.25 mL) for elution, adding NaCl solution (5M, 0.025 mL) and ethanol (1.5 mL) into eluent to precipitate the DNA coding sulfone compound (I-a), wherein the conversion rate is 58%.
Example 2
The same procedure as in example 1 was followed, and DMSO was replaced with DMA as the reaction solvent in the reaction of step 2, to obtain a DNA-encoding sulfone compound (I-a) in a yield of 40%.
Example 3
The same method as that of example 1 is adopted, and the light source in the step 2 reaction is 455nm instead of 365nm, so that the DNA coding sulfone compound (I-a) is obtained with the yield of 39%.
Example 4
The same procedure as in example 1 was used, except that cesium carbonate was replaced with cesium fluoride as the base in the reaction of step 2, to obtain a DNA-encoding sulfone compound (I-a) in a yield of 30%.
Example 5
By adopting the same method as the example 1, the sodium sulfinate in the step 2 takes III-b to replace III-a as the raw material to obtain the DNA coding sulfone compound (I-b) with the yield of 83 percent.
Example 6
Using the same procedure as in example 1, the sulfonium phenylacetate in the reaction of step 1 was substituted for the sulfonium p-methoxyphenylacetate as a starting material to give a DNA-encoded sulfonium salt compound (II-b) in a yield of 74%.
Using the same method as in example 1, the sulfonium salt reacted in step 2 was replaced with II-b and sodium sulfinate was replaced with III-c and the DNA encoded the sulfone compound (I-c) at a conversion of 58%.
Example 7
Using the same method as in example 1, the sulfonium salt reacted in step 2 was replaced with II-b and sodium sulfinate was replaced with III-b and III-a, to give a DNA-encoding sulfone compound (I-d) at a conversion of 86%.
Example 8
Using the same method as in example 1, the o-methylbenzoate sulfonium salt in the reaction of step 1 was used as a starting material in place of the p-methoxyphenylacetic acid sulfonium salt to obtain a DNA-encoded sulfonium salt compound (II-c) in a yield of 84%.
Using the same method as in example 1, the sulfonium salt reacted in step 2 was replaced with II-c and sodium sulfinate was replaced with III-c to obtain DNA-encoding sulfone compound (I-e) with a conversion of 86%.
Example 9
Using the same method as in example 1, the sulfonium salt reacted in step 2 was replaced with II-c and the sodium sulfinate was replaced with III-d to obtain DNA-encoded sulfone compound (I-f) with a conversion of 92%.
Example 10
Using the same procedure as in example 1, the flurbiprofen carboxylic acid-derived sulfonium salt in the reaction of step 1 was used in place of the p-methoxyphenylacetic acid sulfonium salt as a starting material to obtain DNA-encoded sulfonium salt compound (II-d) in a yield of 81%.
Using the same method as in example 1, the sulfonium salt reacted in step 2 was replaced with II-d and sodium sulfinate was replaced with III-c to obtain DNA-encoding sulfone compound (I-g) at a conversion of 27%.
The specific structural formula of the DNA-header is as follows:
Claims (9)
1. a synthesis method of a DNA coding sulfone compound based on ion pair compound electron transfer free radical reaction promoted by light, which is shown in formula (I), is characterized in that:
1) Immobilizing a DNA-encoded sulfonium salt compound having the structure of formula (II) on a resin, and washing with an organic solvent;
2) Adding the immobilized DNA coding sulfonium salt compound with the structure of formula (II), sodium sulfinate with the structure of formula (III) and alkali into an organic solvent, reacting for 2-24 hours at 0-80 ℃ under the irradiation of light with a certain wavelength, removing the reaction solvent, and washing for multiple times;
3) Adding an Elute buffer to Elute the DNA coding sulfone compound with the structure of formula (I), precipitating and centrifuging the product to obtain the DNA coding sulfone compound with the structure of formula (I).
Wherein:
the DNA coding sulfonium salt compound with the structure of formula (II) is a DNA coding compound obtained by connecting an amine compound containing a DNA sequence with a sulfonium salt containing a carboxyl group through an amide bond;
the DNA is a double-stranded nucleotide sequence obtained by polymerizing artificially modified/unmodified nucleotide monomers.
Ar group in the sulfonium salt shown in the formula (II) is aryl, substituted aryl, heteroaryl and substituted heteroaryl; the aromatic ring in the aryl and heteroaryl is selected from benzene, naphthalene, furan, thiophene, pyrrole, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrimidine, indole, quinoline, diazine and triazine; the substituted aryl or substituted heteroaryl group can be a mono-substituted aryl or heteroaryl group or a poly-substituted aryl or heteroaryl group; the substituent is selected from methyl, ethyl and C 3 ～C 6 Alkyl radical, C 3 ～C 6 Cycloalkyl, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, nitrile, aldehyde, acetyl, alkyl ketone, ester, amide, methoxy, amine, hydroxyl, mercapto, alkenyl, alkynyl and phenyl; the Ar group can be a natural product or a medicament containing the functional group;
the X group in the sulfonium salt shown in the formula (II) is selected from oxygen, sulfur, nitrogen, selenium and CH 2 、CH 2 -CH 2 Or, it may be a single bond;
the sulfinic acid sodium R group shown in the formula (III) is selected from aryl, substituted aryl, heteroaryl, substituted heteroaryl and C 1 ～C 6 Alkyl radical, C 3 ～C 6 Cycloalkyl wherein aryl and heteroaryl are selected from phenyl, naphthyl, indolyl, furyl, thienyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, pyridyl, pyrimidinyl, quinolinyl, diazinyl, triazinyl; the substituted aryl or heteroaryl can be mono-substituted aryl or heteroaryl and can also be poly-substituted aryl or heteroaryl, and the substituent is selected from methyl, ethyl and C 3 ～C 6 Alkyl radical, C 3 ～C 6 Cycloalkyl, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, nitrile, aldehyde, acetyl, alkyl ketone, ester, amide, methoxy, amine, hydroxyl, mercapto, alkenyl, alkynyl and phenyl; alkyl is methyl, ethyl, benzyl, hydroxymethyl, C 3 ～C 10 Straight chain alkyl of (1), C 3 ～C 10 Branched alkyl of (5)Base, C 3 ～C 6 Cycloalkyl groups of (a);
the base is DBU (1,8-diazabicycloundec-7-ene), DABCO (1,4-diazabicyclo [2.2.2] octane), TMG (tetramethylguanidine), DMAP (4-dimethylaminopyridine), triethylamine, N-diisopropylethylamine, sodium bicarbonate, sodium carbonate, potassium carbonate, cesium fluoride, sodium phosphate;
the organic solvent is one or a mixture of more of N, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, methanol, ethanol, isopropanol, acetone, 1,4-dioxane, acetonitrile, tetrahydrofuran, toluene, dichloromethane, 1,2-dichloroethane, chloroform, water and an inorganic salt buffer solution;
the molar concentration of the sodium sulfinate is 0.2M, 0.5M, 0.8M, 1.0M and 1.5M;
the molar concentration of the alkali is 0.1M, 0.2M, 0.4M, 0.8M, 1.0M and 1.5M;
the light with certain wavelength is as follows: 13w CFL light, white light, 365nm light, 390nm light, 427nm light, 455nm light, 530nm light;
the reaction temperature is room temperature, 20 ℃, 30 ℃, 40 ℃, 60 ℃ and 80 ℃;
the reaction time is 2 hours, 4 hours, 6 hours, 8 hours, 12 hours, 18 hours, 20 hours and 24 hours.
2. The method of claim 1, wherein the Ar group is a natural product or drug containing the above functional groups, used for the synthesis of DNA encoding biologically active compounds.
3. The method of claim 1, wherein the solvent for the on-DNA reaction is DMSO.
4. The method of claim 1, wherein the base is cesium carbonate.
5. The method of claim 1, wherein the reaction light source is 365nm light.
6. The method of claim 1, wherein the molar concentration of sodium sulfinate is 1.0M.
7. The process of claim 1, preferably wherein the base is present at a molar concentration of 0.4M.
8. The process of claim 1, preferably, the reaction temperature is room temperature.
9. The process of claim 1, preferably the reaction time is 18 hours.
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| CN116239938A (en) * | 2023-03-30 | 2023-06-09 | 江苏海田电子材料有限公司 | High-adhesion solder resist coating and preparation process thereof |
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| CN116239938A (en) * | 2023-03-30 | 2023-06-09 | 江苏海田电子材料有限公司 | High-adhesion solder resist coating and preparation process thereof |
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