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Preparation method of semiprotic compound and product and application of semiprotic compound

A compound and organic compound technology, applied in the field of compound preparation, to achieve the effect of simple product purification and simple preparation method

Active Publication Date: 2021-11-09
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports on the synthesis and functional studies of compounds with semi-protonated structures in vitro from small molecular monomers.

Method used

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  • Preparation method of semiprotic compound and product and application of semiprotic compound
  • Preparation method of semiprotic compound and product and application of semiprotic compound
  • Preparation method of semiprotic compound and product and application of semiprotic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Prepare the nitrate of semi-protonic compound imidazole-imidazole, concrete method is as follows:

[0033] Dissolve 1 g of white imidazole in 10 mL of water, then add excess NH 4 NO 3 Aqueous solution (NH 4 NO 3 The molar ratio with imidazole is 2:1). Stir the reaction at room temperature for 12 hours, add excess chloroform to dissolve the product after freeze-drying, and separate the product by column chromatography to obtain light brown semi-protic imidazole-imidazole nitric acid with a melting point of 174-176°C.

[0034] 1H NMR (400MHz, Deuterium Oxide): δ7.68(s, 2H), 6.39(s, 1H), 3.59(t, J=7.4Hz, 1H), 1.13(t, J=7.1Hz, 2H). HRMS: [C 6 h 9 N 4 ]NO 3 , molecular ion peak 137.2. Its structure is as follows:

[0035]

Embodiment 2

[0037] Preparation of semi-protic compound thiophene-thiophene hexafluorophosphoric acid, the specific method is as follows:

[0038] Dissolve 1 g of thiophene in 10 mL of ethanol solution, then add excess NH 4 PF 6 Alcoholic solution (wherein NH 4 PF 6 The molar ratio to thiophene is 1.5:1), mix well at room temperature, add appropriate amount of acetonitrile to dissolve the product after freeze-drying, filter the supernatant, and dry to obtain a light yellow product with a melting point of 89-91°C.

[0039] 1H NMR(400MHz,DMSO-d6):δ8.33-8.23(m,5H),8.03-7.94(m,5H),7.23(s,1H),7.10(s,1H),6.98(s,1H) . HRMS: [C 8 h 9 S 2 ]PF 6 , molecular ion peak 169.3. Its structure is as follows:

[0040]

Embodiment 3

[0042] Preparation of semi-protic compound purine-pyrimidine hexafluorophosphate, the specific method is as follows:

[0043]Dissolve 1 g of white purine and white pyrimidine (the molar ratio of purine to pyrimidine is 1:1) in 10 mL of water, stir at room temperature for 2 h, and then add NH with a molar ratio of 3:1 4 PF 6 Aqueous solution (where NH 4 PF 6 The molar ratio to purine is 3:1), after lyophilization, add an appropriate amount of acetonitrile to dissolve the product, filter the supernatant, and dry to obtain light yellow semi-protic purine-pyrimidine hexafluorophosphate, with a melting point of 228-230°C.

[0044] 1H NMR (400MHz, Deuterium Oxide) δ9.10(d, J=1.9Hz, 1H), 8.92(s, 1H), 8.57(s, 1H), 4.74(s, 8H), 4.63(s, 5H). HRMS: [C 9 h 9 N 6 ]PF 6 , molecular ion peak 201.2. Its structure is as follows:

[0045]

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Abstract

The invention relates to a preparation method of a semiprotic compound and a product and application thereof, and belongs to the technical field of compound preparation. The invention discloses the preparation method of a semiprotic compound, which comprises the following step: reacting a heteroalkyl organic compound or a heterocyclic organic compound under the action of ammonium salt to prepare the semiprotic compound. The synthesis method of the compound is shown in the general formula. The preparation method of the semi-protic compound is simple, and the obtained semi-protic compound has biological activities such as reducibility, antibiosis and antineoplastic activity.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, and relates to a preparation method of a semi-protic compound and its product and application. Background technique [0002] A semi-protonated compound is a protonated molecule that interacts with another unprotonated molecule through hydrogen bonding to form a stable semi-protonated structure. The structure of the semi-protic compound appears in a DNA repeat fragment (i-motif structure) rich in cytosine (Cytosine, C) bases, two C and N + -H … N hydrogen bonds to become C-C + , this unique structure has functions such as regulating telomere length and gene expression. However, there are no reports on the synthesis and functional studies of compounds with semi-protonated structures in vitro from small molecular monomers. [0003] The H in the semi-protic compound can be used as an active proton donor for the reduction reaction of other substances; at the same time, biological func...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/58C07D333/10C07D239/26C07D487/04C07D213/22C07D471/22C07D215/06C07D241/12C07D473/34C07D233/64C07D209/20C07D241/46C07H19/173C07H1/00C07D471/04C07C211/05C07C209/00A61P35/00A61P39/06A61P31/04A61P31/10
CPCC07D233/58C07D333/10C07D239/26C07D487/04C07D213/22C07D471/22C07D215/06C07D241/12C07D473/34C07D233/64C07D209/20C07D241/46C07H19/173C07H1/00C07D471/04C07C211/05C07C209/00A61P35/00A61P39/06A61P31/04A61P31/10
Inventor 付爱玲赵梓圳付琛
Owner SOUTHWEST UNIV