2-mercapto-1,3,4-thiadiazole derivative, and preparation method and application thereof

A technology of thiadiazole derivatives and thiadiazoles, applied in the directions of botanical equipment and methods, applications, biocides, etc., to achieve the effects of mild conditions, broad-spectrum antibacterial activity and high yield

Inactive Publication Date: 2014-02-19
XINXIANG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Thiol groups can also be used as hydrogen bond donors, but there is no literature report

Method used

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  • 2-mercapto-1,3,4-thiadiazole derivative, and preparation method and application thereof
  • 2-mercapto-1,3,4-thiadiazole derivative, and preparation method and application thereof
  • 2-mercapto-1,3,4-thiadiazole derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0027] Example 1

[0028] Synthesis of N,N'-bis((2'-mercapto-1',3',4'-thiadiazole)-5')-5-nitro-1,3-dimethylaminobenzene

[0029] 2-Mercapto-5-amino-1,3,4-thiadiazole (2mmol, 266mg) was dissolved in absolute ethanol (20mL), and 3 drops of glacial acetic acid were added under magnetic stirring, 5-nitro-1,3- Phthalaldehyde (1 mmol, 179 mg) was added dropwise to the above solution. In a nitrogen atmosphere, the mixture was heated to reflux for 12 h. After the reaction was completed, cooled and filtered with suction to obtain a yellow target product, which was recrystallized from absolute ethanol, washed with ether, and dried in vacuo to obtain a yellow solid. Yield: 87%. 1 H NMR (400MHz, DMSO-d 6 , 298K) δ13.17 (s, 2H, SH), 10.64 (s, 2H, CH), 7.09 (s, 3H, ph-H). Elemental Analysis: Calculated Value C 12 h 7 N 7 o 2 S 4 : C, 35.20; H, 1.72; N, 23.94; Experimental values: C, 35.51; H, 1.29; N, 24.18. ESI-MS(m / z):407.8(M-H) - .

Example Embodiment

[0030] Example 2

[0031] UV-Vis Absorption Spectroscopy Experiment

[0032] The compound N,N'-bis((2'-mercapto-1',3',4'-thiadiazole)-5')-5-nitro-1,3-dimethylamine synthesized by the present invention Base benzene is the main body dubbed 1×10 -3 mol / L dimethyl sulfoxide solution, the anion tetrabutylammonium salts are tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium Ammonium acetate and tetrabutyl ammonium dihydrogen phosphate are both made into 2×10 -3 mol / L dimethyl sulfoxide solution. Pipette 0.2mL of the main body solution into a series of 5mL colorimetric tubes, add a certain volume of anion tetrabutylammonium salt solution to each colorimetric tube, and then dilute to the mark with dimethyl sulfoxide solvent to obtain a series of main body For solutions with constant concentration and different anion concentrations, the absorption spectrum is measured after mixing evenly, and the dimethy...

Example Embodiment

[0038] Example 3

[0039] Fluorescence emission spectroscopy experiments

[0040] The compound N,N'-bis((2'-mercapto-1',3',4'-thiadiazole)-5')-5-nitro-1,3-dimethylamine synthesized by the present invention Base benzene is the main body dubbed 1×10 -3 mol / L dimethyl sulfoxide solution, the anion tetrabutylammonium salts are tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium iodide, tetrabutylammonium Ammonium acetate and tetrabutyl ammonium dihydrogen phosphate are both made into 2×10 -3 mol / L dimethyl sulfoxide solution. Pipette 0.2mL of the main body solution into a series of 5mL colorimetric tubes, add a certain volume of anionic tetrabutylammonium salt solution to each colorimetric tube, and then dilute to the mark with dimethyl sulfoxide to obtain a series of compound concentrations For solutions with constant and different anion concentrations, measure their fluorescence emission spectra after mixing evenly, and us...

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Abstract

The invention discloses a 2-mercapto-1,3,4-thiadiazole derivative having a general formula I and a preparation method and application thereof. According to the method, meta-substituted phthalaldehyde reacts with 2-mercapto-5-amino-1,3,4-thiadiazole in ethanol so as to prepare a compound having the general formula I. The prepared 2-mercapto-1,3,4-thiadiazole derivative has broad-spectrum antibacterial activity, is capable of selectively recognizing dihydrogen phosphate ions, provides a critical basis for screening of lead compounds and has an application value in quantitative determination of dihydrogen phosphate ions in biological, environmental and medicinal samples and the like.

Description

technical field [0001] The invention relates to the fields of chemical synthesis, molecular recognition and biological activity, in particular to a preparation method of 2-mercapto-1,3,4-thiadiazole derivatives, and the invention also discloses that the thiadiazole derivatives are used in anion detection and antibacterial active use. Background technique [0002] As we all know, thiadiazole derivatives are an important class of heterocyclic compounds, which have various biological activities such as anticancer, antibacterial, and antifungal. In particular, the "carbon nitrogen sulfur" structure of 1,3,4-thiadiazole derivatives can be used as an active center to chelate certain metal ions in organisms, and has better cell tissue permeability. Moreover, the introduction of heterocyclic rings with different skeletons into the thiadiazole core will affect its biological activity. Therefore, the synthesis of thiadiazole compounds with novel structures has become one of the hot ...

Claims

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Application Information

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IPC IPC(8): C07D285/135G01N21/64G01N24/08G01N21/33A61P31/04
CPCA01N43/82C07D285/135G01N21/33G01N21/64G01N24/08G01N2021/3155Y02A50/30
Inventor 尚学芳程迪王煜霞王雷杜锦阁付志远魏晓芳
Owner XINXIANG MEDICAL UNIV
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