CN108395426B - Schiff base derivative containing thiadiazole and quinoline structure and preparation application thereof - Google Patents
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Abstract
The invention provides a Schiff base derivative containing thiadiazole and quinoline structures, and a preparation method and application thereof, wherein the Schiff base derivative containing thiadiazole and quinoline structures has a chemical structural general formula as follows:
Description
Technical Field
The invention relates to the technical field of drug synthesis, in particular to a Schiff base derivative containing thiadiazole and quinoline structures, and a preparation method and application thereof.
Background
So far, a great deal of research documents about Schiff base compounds have been reported, and particularly, the synthesis and application of the Schiff base compounds are remarkably advanced, and the Schiff base compounds can be substituted by different groups or various functional groups are introduced according to structural composition characteristic analysis of the Schiff base per se, so that the Schiff base compounds have very important chemical and biological meanings.
The Schiff base compound can be prepared by flexibly selecting reactants, namely, Schiff base derivatives with rich structures and properties are designed and synthesized by changing the types and positions of substituents. The Schiff base compound is used as a ligand molecule, and can form a stable coordination compound by a plurality of elements. The complexes have important significance in the disciplines of analytical chemistry, electrochemistry, molecular self-assembly, supermolecular chemistry, bionics science, catalysis, materials and the like.
Researches show that the quinoline compound has stronger biological and pharmacological activities, such as biological activities of resisting cancer, bacteria, inflammation, viruses and the like, and quinoline is not only an important drug but also a good drug intermediate and is widely concerned in the research and development of drugs. The thiadiazole compound and Schiff base compound also have high biological activity, and are particularly prominent in antibacterial aspect. However, in the prior art, quinoline compounds, thiadiazole compounds and Schiff base compounds are not applied together.
In view of the above, the present invention is particularly proposed.
Disclosure of Invention
The first purpose of the invention is to provide a Schiff base derivative containing thiadiazole and quinoline structures, wherein the Schiff base derivative contains a thiadiazole structure and a quinoline structure at the same time, and the Schiff base derivative with a specific structure is a compound which is screened by an inventor according to actually detected antibacterial activity and has a good antibacterial curative effect.
The second purpose of the invention is to provide the preparation method of the Schiff base derivatives, which has the advantages of mild reaction conditions, no need of harsh conditions such as high pressure, inert environment and the like, convenient operation, non-flammable and non-explosive reaction raw materials, no severe toxicity, safer synthetic route, no by-products, simple reaction route and wide popularization and application value.
The third purpose of the invention is to provide further application of the Schiff base derivatives, which can be better applied to the field of antibacterial drug preparation.
In order to solve the technical problems, the invention provides the following technical scheme:
the embodiment of the invention provides a Schiff base derivative containing thiadiazole and quinoline structures, which has a chemical structural general formula as follows:
wherein, R is one of H, Cl, Me and OMe.
In the prior art, Schiff base compounds can be prepared by flexibly selecting reactants, namely Schiff base derivatives with rich structures and properties are designed and synthesized by changing the types and positions of substituents. The Schiff base compound is used as a ligand molecule, and can form a stable coordination compound by a plurality of elements. The complexes have important significance in the disciplines of analytical chemistry, electrochemistry, molecular self-assembly, supermolecular chemistry, bionics science, catalysis, materials and the like.
Researches show that the quinoline compound has stronger biological and pharmacological activities, such as biological activities of resisting cancer, bacteria, inflammation, viruses and the like, and quinoline is not only an important drug but also a good drug intermediate and is widely concerned in the research and development of drugs. The thiadiazole compound and Schiff base compound also have high biological activity, and are particularly prominent in antibacterial aspect. However, in the prior art, quinoline compounds, thiadiazole compounds and Schiff base compounds are not applied together.
In order to solve the technical problems, the invention provides a Schiff base derivative with a brand-new structure and containing thiadiazole and quinoline structures, and the Schiff base derivative is used for detecting the antibacterial activity of the Schiff base derivative and searching a compound with a better antibacterial curative effect. The compound has good antibacterial effect, stable structure, convenient synthesis and wide application, and is worthy of expanding popularization.
The embodiment of the invention also provides a preparation method of the Schiff base derivative containing thiadiazole and quinoline structures, which comprises the following steps:
(A) will be provided with
Heating and refluxing thiosemicarbazide and phosphorus oxychloride,cooling after reaction, adjusting pH, and concentrating to obtain
(B) Mixing the obtained substance with
Dissolving in solvent, reacting for 2-3h to obtain;
wherein, R is one of H, Cl, Me and OMe.
The chemical process route of the preparation method is as follows:
preferably, in the step (A), the pH is adjusted to 7-9, and the pH value is controlled in a relatively proper range, so that the ordered reaction is more facilitated, and the ordered performance of the subsequent concentration step is also facilitated.
Preferably, in the step (A), the pH is adjusted by using an organic base or an inorganic base, and in general, the pH is directly adjusted by using an alkali solution, such as sodium hydroxide, in practical operation.
Preferably, in the step (a), after the reaction is cooled to room temperature, the reaction solution is poured into ice water for further cooling.
Preferably, in the step (a), the concentration method comprises: vacuum filtering, drying, and recrystallizing.
Preferably, ethanol is used for recrystallization.
Preferably, in the step (B), the solvent is methanol or ethanol, more preferably methanol.
Preferably, in the step (B),
and
the amount of material between the two is equal.
The Schiff base derivative containing thiadiazole and quinoline structures provided by the embodiment of the invention has good application in the aspect of preparing antibacterial drugs.
Compared with the prior art, the invention achieves the following technical effects:
(1) the Schiff base derivative simultaneously contains a thiadiazole structure and a quinoline structure, and is a compound with a specific structure and a good antibacterial effect, which is screened by an inventor according to the actually detected antibacterial activity;
(2) the preparation method of the Schiff base derivatives has mild reaction conditions, does not need harsh conditions such as high pressure, inert environment and the like, is convenient to operate, has non-flammable and explosive reaction raw materials, has no severe toxicity, safer synthetic route, no by-product and simple reaction route, and is worthy of wide popularization and application.
(3) The Schiff base derivative can be well applied to the field of antibacterial drug preparation, and provides a brand new technology for the preparation of antibacterial drugs.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following detailed description, but those skilled in the art will understand that the following described examples are some, not all, of the examples of the present invention, and are only used for illustrating the present invention, and should not be construed as limiting the scope of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The structural formula of compound a in the following examples is:
the structural formula of the compound B is as follows:
example 1
The preparation method of 8- (1, 3, 4-thiadiazole benzimide) quinoline (compound 1) is as follows:
the structural formula of the compound is as follows:
1) a 50ml flask was charged with 3.26g of compound a, 2.74g of thiosemicarbazide, and 20ml of phosphorus oxychloride, heated under reflux, followed by TLC, the reaction was cooled to room temperature, and the reaction mixture was poured into ice water and adjusted to pH 8 with a base.
2) And (3) carrying out vacuum filtration to obtain a yellow solid, drying, and recrystallizing by using ethanol to obtain a yellow solid B.
3) 2.28 g of the compound B and 1.062g of benzaldehyde with the same mass are taken to be added into methanol for dissolving, the mixture is stirred and reacted for 2 to 3 hours at normal temperature, yellow solid is separated out, and the yellow solid is recrystallized by methanol to obtain the target product.
The appearance of the target product is yellow powder, the yield of the preparation method can reach 62 percent through detection, and Mp is 152-154 ℃;1HNMR(300MHz，DMSO-d6)：δ9.05-9.04(d,J＝3Hz,1H),8.38(s,1H),8.27-8.26(d,J＝3Hz,1H),7.95-7.92(m,2H),7.70-7.67(m,1H),7.55-7.44(m,6H),MS(ESI:317.08(C18H13N4S，[M+H]+).Anal.Calcd for C17H18N4s is C, 68.33; h, 3.82; n, 17.71%. Found: c, 68.39; h, 3.76; n, 17.82%, the nuclear magnetic data can achieve the purpose of confirming the structure of the compound.
Example 2
The preparation method of 8- (1, 3, 4-thiadiazole p-toluidine) quinoline (compound 2) comprises the following steps:
the structural formula of the compound is as follows:
the other procedure was identical to example 1 except that benzaldehyde was replaced by methylbenzaldehyde and the pH was adjusted to 7.
The appearance of the target product is yellow powder, the yield of the preparation method can reach 67 percent through detection, and the Mp is 136-138 ℃;1HNMR(300MHz，DMSO-d6)：δ9.05-9.04(d,J＝3Hz,1H),8.27-8.26(d,J＝3Hz,1H),8.19(s,1H),7.95-7,92(m,2H),7.70-7.67(m,1H),7.54-7.47(m,3H),7.24-7.23(d,J＝3Hz,2H),2.30(s,3H)MS(ESI:331.09(C19H15N4S，[M+H]+).Anal.Calcd for C19H14N4s, C, 69.07; h, 4.27; n, 16.96%. Found: c, 69.13; h, 4.25; n, 16.92%, the nuclear magnetic data can achieve the purpose of confirming the structure of the compound.
Example 3
The preparation method of 8- (1, 3, 4-thiadiazole p-methoxybenzene imine) quinoline (compound 3) comprises the following steps:
the structural formula of the compound is as follows:
the other steps were identical to those of example 1, except that benzaldehyde was replaced by p-methoxybenzaldehyde, and the pH was adjusted to 9.
The appearance of the target product is yellow powder, the yield of the preparation method can reach 65 percent through detection, and Mp is 132-134 ℃;1HNMR(300MHz，DMSO-d6)：δ9.05-9.04(d,J＝3Hz,1H),8.27-8.26(d,J＝3Hz,1H),8.19(s,1H),7.95-7,92(m,2H),7.70-7.67(m,1H),7.54-7.47(m,3H),7.24-7.23(d,J＝3Hz,2H),3.84(s,3H)MS(ESI:347.09(C19H15N4OS，[M+H]+).Anal.Calcd for C19H14N4OS C, 65.88; h, 4.07; n, 16.17%. Found: c, 65.83; h, 4.09; n, 16.21%, the nuclear magnetic data can achieve the purpose of confirming the structure of the compound.
Example 4
The preparation method of 8- (1, 3, 4-thiadiazole p-chlorobenzeneimine) quinoline (compound 4) comprises the following steps:
the structural formula of the compound is as follows:
the other procedure was identical to example 1 except that benzaldehyde was replaced by p-chlorobenzaldehyde, followed by replacing the methanol solvent by ethanol.
The appearance of the target product is yellow powder, the yield of the preparation method can reach 60 percent through detection, and Mp189-191 ℃;1HNMR(300MHz，DMSO-d6)：δ9.05-9.04(d,J＝3Hz,1H),8.27-8.26(d,J＝3Hz,1H),8.19(s,1H),7.95-7,92(m,2H),7.70-7.67(m,1H),7.54-7.47(m,3H),7.24-7.23(d,J＝3Hz,2H),MS(ESI:351.04(C18H12ClN4S，[M+H]+).Anal.Calcd for C18H11ClN4s, C, 61.63; h,3, 16; n, 15.97%. Found: c, 61.59; h, 4.12; n, 15.83%, the nuclear magnetic data can achieve the purpose of confirming the structure of the compound.
Experimental example 1 study on antibacterial activity of Schiff base derivatives containing thiadiazole and quinoline structures
1.1 drugs and reagents:
Mueller-Hinton medium (beef extract powder 5g, casein hydrolysate 17.5g, starch 1.5g, agar 12.5g, added to 1000mL of distilled water), kanamycin, penicillin, DMSO, MTT (3- (4, 5-dimethylthiazole-2) -2, 5-diphenyltetrazolium bromide, trade name thiazole blue), isopropanol, hydrochloric acid, all of the analytical reagents, synthesized compounds 1-4 (compounds in examples 1-4), PBS buffer (phosphate buffer 0.01mol/L, pH7.4, Na, pH 7.4)2HPO4.12H2O 2.9g，KH2PO40.2g, NaCl8.0g, KCl 0.2g, and distilled water 1000 mL).
1.2 strains:
escherichia coli (e.coli), staphylococcus aureus (s.aureus), bacillus subtilis (b.subtilis), pseudomonas aeruginosa (p.aeruginosa)
1.3 Experimental methods:
1.3.1 preparation of culture Medium:
adding 5g of beef extract powder, 17.5g of casein hydrolysate, 1.5g of starch and 12.5g of agar into 1000mL of distilled water, heating to boil and dissolve, subpackaging, and autoclaving at 121 ℃ for 15 minutes for later use.
1.3.2 culture of test bacteria:
taking four test strains of escherichia coli, staphylococcus aureus, bacillus subtilis and pseudomonas aeruginosa in a sterile room, scraping a small amount of slant lawn on slants of the four test strains by using an inoculating needle under an alcohol lamp, preparing bacterial suspension by using a certain amount of sterile water, then adding a certain amount of the bacterial suspension into a molten MH culture medium cooled to about 50 ℃, shaking uniformly, immediately pouring the mixture into a sterile culture dish, sealing the culture dish by using a rubber plug after full condensation, and culturing the mixture for 18-24 hours at 37 ℃ for later use. Sucking 1mL of bacterial liquid, and diluting the bacterial liquid with MH culture medium according to the ratio of 1: 1000 to ensure that the concentration of the bacterial liquid is about 105 cfu/mL.
1.3.3 antibacterial experiments:
the substance prepared in the invention example 1 is dissolved in DMSO to prepare a solution of 2mg/mL, and then the medicine is diluted into a certain concentration gradient (50 mug/mL, 25 mug/mL, 12.5 mug/mL, 3.125 mug/mL) and DMSO by a double dilution method. mu.L of the medium was added to the first strip of the sterilized microtiter plate, and 100. mu.L of the bacterial suspension was added to the second strip, which was a positive control. The remaining wells were filled with 90. mu.L of the bacterial suspension and 10. mu.L of the drug solution. Each drug solution concentration was replicated 3 times. The bacterial name is indicated at the bottom of the microtiter plate. The treated dishes were incubated at 37 ℃ for 24 hours and observed.
1.3.4 determination of MIC:
after each microtiter plate was visually assayed for its MIC, 50. mu.L PBS buffer (0.01 mol/L phosphate buffer, pH7.4, Na2HPO4.2H2O 2.9g, KH2PO40.2g, NaCl8.0g, KCl 0.2g, distilled water 1000mL) containing 2mg MTT/mL was added to each well of the plate. Incubation was continued at room temperature for 4-5 h. The contents of the wells were removed and 100. mu.L of isopropanol containing 5% 1mol/L HCl was added to extract the dye. Incubation was continued at room temperature for 12h, and the absorbance (OD value) of each well was measured with a microplate reader, and the wavelength was measured at 550 nm. The minimum inhibitory concentration of drug on bacterial growth was calculated from the OD values of each well.
Minimum Inhibitory Concentration (MIC): after 24 hours of incubation in a specific environment, the minimum inhibitory concentration which is the lowest drug concentration capable of inhibiting the obvious growth of a certain microorganism is prepared, a standard curve of the bacterial growth inhibition rate is prepared according to the measured optical density (OD value), and the corresponding drug concentration is obtained on the standard curve. The measured MICs are shown in Table 1.
TABLE 1 MIC values (μ g/mL) for inhibition of bacteria by Schiff base derivatives containing thiadiazole and quinoline structures according to the present invention
Positive control: chloramphenicol; penicillin
The results show that: the Schiff base derivatives containing thiadiazole and quinoline structures in the embodiment of the invention have different degrees of inhibition effects on Escherichia coli (E.coli), staphylococcus aureus (S.aureus), bacillus subtilis and pseudomonas aeruginosa, and have the same result when being measured on Schiff base derivatives in other embodiments.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (11)
1. A Schiff base derivative containing thiadiazole and quinoline structures is characterized in that the chemical structural general formula of the Schiff base derivative is as follows:
wherein, R is one of H, Cl, Me and OMe.
2. The preparation method of the Schiff base derivatives containing thiadiazole and quinoline structure as claimed in claim 1, which comprises the following steps:
(A) will be provided with
Heating and refluxing thiosemicarbazide and phosphorus oxychloride, cooling after reaction, adjusting pH, and concentrating to obtain the final product
(B) Mixing the obtained substance with
Dissolving in solvent, reacting for 2-3h to obtain;
wherein, R is one of H, Cl, Me and OMe.
3. The method according to claim 2, wherein in the step (A), the pH is adjusted to 7 to 9.
4. The production method according to claim 2 or 3, wherein in the step (A), the pH is adjusted using an organic base or an inorganic base.
5. The method according to claim 2, wherein in the step (A), after the reaction is cooled to room temperature, the reaction solution is poured into ice water and further cooled.
6. The method according to claim 2, wherein in the step (A), the concentration method comprises: vacuum filtering, drying, and recrystallizing.
7. The method according to claim 6, wherein ethanol is used for recrystallization.
8. The method according to claim 2, wherein in the step (B), the solvent is methanol or ethanol.
9. The method according to claim 8, wherein the solvent in the step (B) is methanol.
10. The production method according to claim 2, wherein in the step (B),
and
the amount of material between the two is equal.
11. The use of the Schiff base derivatives containing thiadiazole and quinoline structure according to claim 1 in the preparation of antibacterial agents.
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Patent Citations (2)
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| CN102675302A (en) * | 2011-03-17 | 2012-09-19 | 南京大学 | Thiadiazole derivative containing 1,4-benzdioxanand preparation method and antibacterial activity thereof |
| CN103664910A (en) * | 2012-09-14 | 2014-03-26 | 南京大学 | 1,2,4-triazole derivatives containing 1,4-benzodioxane, and preparation method and antibacterial activity thereof |
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