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Aryl 1,2,4-triazole nucleoside compounds as well as preparation method and application thereof

A ribavirin compound and compound technology are applied in the preparation of sugar derivatives, chemical instruments and methods, drug combinations, etc., and can solve the problems of poor water solubility and high onset concentration, and achieve low cost, mild reaction conditions, and high yield. high rate effect

Active Publication Date: 2020-01-21
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this kind of aryl 1,2,4-triazazole ribavirin analogue has the defects of poor water solubility and high effective concentration like most nucleoside analogues

Method used

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  • Aryl 1,2,4-triazole nucleoside compounds as well as preparation method and application thereof
  • Aryl 1,2,4-triazole nucleoside compounds as well as preparation method and application thereof
  • Aryl 1,2,4-triazole nucleoside compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Prepare intermediate compound II-1-1 according to the following reaction formula:

[0045]

[0046] With substituent R 2 for Compound II-1-1-1 prepares intermediate compound II-1-1, according to the substituent R 2 Differently named it as II-1-1a~II-1-1i, where the substituent R 4 The relationship with each compound involved in the reaction is shown in Table 1.

[0047] Table 1 Substituent R 2 in accordance with R 4 Corresponding relationship of different preparations of corresponding intermediates II-1-1

[0048] R 4

-H -CH 3

-C 3 h 7

-C 4 h 9

-C 5 h 11

-C 7 h 15

-OCH 3

-CF 3

-F II-1-1-1 II-1-1-1a II-1-1-1b II-1-1-1c II-1-1-1d II-1-1-1e II-1-1-1f II-1-1-1g II-1-1-1h II-1-1-1i II-1-1-2 II-1-1-2a II-1-1-2b II-1-1-2c II-1-1-2d II-1-1-2e II-1-1-2f II-1-1-2g II-1-1-2h II-1-1-2i II-1-1 II-1-1a II-1-1b II-1-1c II-1-1d II-1-1e II-1-1f II-1-1...

Embodiment 2

[0054] Prepare intermediate compound II-1-2 according to the following reaction formula, adopt substituent R 2 for The compound II-1-2-1 (wherein the difference between compound II-1-2-1 and compound II-1-1-1 is R 2 different substitution positions) to prepare intermediate compound II-1-2, according to substituent R 2 Differently named it as II-1-2a~II-1-2i, where the substituent R 4 The relationship with each compound involved in the reaction is shown in Table 2:

[0055]

[0056] Table 2 Substituent R 2 in accordance with R 4 Correspondence of different preparations of corresponding intermediates II-1-2

[0057] R 4

-H -CH 3

-C 3 h 7

-C 4 h 9

-C 5 h 11

-C 7 h 15

-OCH 3

-CF 3

-F II-1-2-1 II-1-2-1a II-1-2-1b II-1-2-1c II-1-2-1d II-1-2-1e II-1-2-1f II-1-2-1g II-1-2-1h II-1-2-1i II-1-2-2 II-1-2-2a II-1-2-2b II-1-2-2c II-1-2-2d II-1-2-2e II-1-2-2f II-1-2-2g II-1-2-...

Embodiment 3

[0062] Prepare intermediate compound II-1-3 according to the following reaction formula:

[0063]

[0064] With substituent R 2 for Compound II-1-3-1 prepares intermediate compound II-1-3, according to the substituent R 4 Differently named it as II-1-3a~II-1-3i, where the substituent R 4 The relationship with each compound involved in the reaction is shown in Table 3.

[0065] Table 3 Substituent R 2 in accordance with R 4 Corresponding relationship of different preparations of corresponding intermediates II-1-3

[0066] R 4

-H -CH 3

-C 3 h 7

-C 4 h 9

-C 5 h 11

-C 7 h 15

-OCH 3

-CF 3

-F II-1-3-1 II-1-3-1a II-1-3-1b II-1-3-1c II-1-3-1d II-1-3-1e II-1-3-1f II-1-3-1g II-1-3-1h II-1-3-1i II-1-3-2 II-1-3-2a II-1-3-2b II-1-3-2c II-1-3-2d II-1-3-2e II-1-3-2f II-1-3-2g II-1-3-2h II-1-3-2i II-1-3 II-1-3a II-1-3b II-1-3c II-1-3d II-1-3e II-1-3f II-1-3...

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Abstract

The invention relates to aryl 1,2,4-triazole nucleoside compounds as well as a preparation method and application thereof, and belongs to the field of compound synthesis. According to the method, thearyl 1,2,4-triazole nucleoside is adopted as a lead compound, aryl and 1,2,4-triazole are connected by adopting alkynyl or 1,2,3-triazole as a connecting group, and then different amino groups are utilized to replace terminal hydroxyl of the aryl 1,2,4-triazole nucleoside glycosyl part to obtain a series of novel triazole nucleoside compounds shown as a general formula I. The anticancer and antibacterial effects of the synthesized compounds are tested and prove that the aryl 1,2,4-triazole nucleoside compounds disclosed by the invention have good anticancer and antibacterial effects.

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to an aryl 1,2,4-ribavirin compound and its preparation method and application. Background technique [0002] Nucleoside analogs are an important class of drug molecules used clinically. These compounds generally participate in important life regulation processes in the body by simulating the structure of natural nucleosides, such as inhibiting the synthesis of DNA or RNA, or affecting the activation of key enzymes in cells. activity, thereby achieving the effect of inhibiting the growth of tumor cells or microorganisms. At present, nucleoside analogs are widely used in the treatment of cancer, virus, bacteria, fungal infection and other diseases. Common nucleoside drugs include Gemcitabine, Capecitabine, Decitabine and Ribavirin. The use of these nucleoside drugs can treat various diseases that endanger human health, but the long-term use of drugs also brings problem...

Claims

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Application Information

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IPC IPC(8): C07D249/10C07H19/056C07H1/00A61P35/00A61P31/04
CPCC07D249/10C07H19/056C07H1/00A61P35/00A61P31/04Y02A50/30
Inventor 夏熠张燕华刘茜罗碧瑶陈迷谜
Owner CHONGQING UNIV