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Chromone-containing benzimidazole bifurazan compound with Cy-FBP/SBPase inhibition effect and preparation method of chromone-containing benzimidazole bifurazan compound

A benzimidazole and inhibition technology, applied in the field of chromone-containing benzimidazole bifurazan compounds and their preparation

Pending Publication Date: 2020-08-25
JIANGXI SCI & TECH NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention aims at the technical defects of the prior art, and provides a chromone-containing benzimidazole-bifurazan compound with Cy-FBP / SBPase inhibitory effect and a preparation method thereof, so as to solve the problems that do not exist in the prior art. Technical Problems of Structural Compounds

Method used

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  • Chromone-containing benzimidazole bifurazan compound with Cy-FBP/SBPase inhibition effect and preparation method of chromone-containing benzimidazole bifurazan compound
  • Chromone-containing benzimidazole bifurazan compound with Cy-FBP/SBPase inhibition effect and preparation method of chromone-containing benzimidazole bifurazan compound
  • Chromone-containing benzimidazole bifurazan compound with Cy-FBP/SBPase inhibition effect and preparation method of chromone-containing benzimidazole bifurazan compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Intermediate MAOC

[0043] Preparation of 4-amino-1,2,5-oxadiazole-3-methoxyamidine (referred to as MAOC)

[0044]

[0045] Take 3.75g (57mmol) of malononitrile, 4.3g (62mmol) of sodium nitrite and 10mL of water and mix evenly and dissolve completely. Keeping at 0°C, slowly add 0.8mL of acetic acid dropwise, then stir at room temperature for 6 hours, the reaction solution turns from light yellow to orange red. Dissolve 9g (130mmol) of hydroxylamine hydrochloride in 14mL of water, and slowly add it dropwise, keeping the temperature below 20°C, a large amount of yellow foam is formed. The pH of the reaction solution was adjusted to 10 with 25% sodium hydroxide solution, and the reaction solution turned red and clear. Keep the reaction at 30°C for 10 hours, and then heat to reflux for 3 hours. After cooling, a yellow substance precipitated out. Suction filtration, washing, and drying gave 3.89 g (yield 45%) of light yellow powder 3-amino-4-amidoxime furoxan (AAOF). ...

Embodiment 2

[0050] Intermediate II

[0051] Preparation of 3-(2-(4-amino-1,2,5-oxadiazole-3-)-1hydro-benzo[d]imidazole-1-)propionhydrazide (Intermediate II)

[0052]

[0053] Take 2.24g (20mmol) of o-phenylenediamine and dissolve it in 15mL of ethanol, add 1.43g (10mmol) of K 2 CO 3 , 3.76g (20mmol) ethyl bromopropionate, stirred at room temperature for 50 hours. Suction filtration, the filtrate was rotary evaporated to obtain a black mixture. With PE:EtOAc=1:1 column chromatography, one of the pure components was obtained as a red oily substance 3-((2-aminophenyl)amino) ethyl propionate (intermediate K) 0.88g (yield 20% ). 1 H NMR (400MHz, CDCl 3 )δ6.88-6.60 (m, 4H, ArH), 4.15 (q, J=7.2Hz, 2H, O-CH 2 ), 3.44(t, J=6.0Hz, 2H, N-CH 2 ), 2.66(t, J=6.0Hz, 2H, O=C-CH 2 ), 1.26(t, J=7.2Hz, 3H, CH 3 ).

[0054] Take 0.88g (4.2mmol) ethyl 3-((2-aminophenyl)amino)propionate (Intermediate K), 0.60g (4.2mmol) 4-amino-1,2,5-oxadiazole-3 - Place methoxyamidine (MAOC) in a round bottom fl...

Embodiment 3

[0058] Compound I-1

[0059] Preparation of 3-[2-(4-aminofurazan-3-)-benzimidazole-1-]-propionic acid (4-oxo-4hydro-chromone-3-methylene)-hydrazide

[0060]

[0061] Take 287mg (1mmol) of Intermediate II and 1mmol of 3-formylchromone, mix and dissolve in 25ml of ethanol, add 3 drops of HOAc dropwise, and stir r.t. for 2h, a large amount of insoluble matter is formed. TLC monitors that the reaction is almost complete. Suction filtration, and wash with a large amount of ethanol several times, dry, obtain white powder, 3-[2-(4-aminofurazan-3-)-benzimidazole-1-]-propionic acid (4-oxo -4hydro-chromone-3-methylene)-hydrazide, 83% yield, m.p.218-220°C.

[0062] Molecular formula: C 22 h 17 N 7 o 4 ;

[0063] 1 H NMR (600MHz, DMSO-d 6 )δ11.60-11.31(m,1H,NH),8.81–7.21(m,10H,=CH-O,CH=N,ArH),7.12-6.80(m,2H,NH 2 ),5.13–4.78 (m,2H,CH 2 ),3.24-2.71(m,2H,CH 2 ); HR-MS (ESI): m / z=444.1356, calcd for C 22 h 17 N 7 o 4 [M+H] + :444.1342.

[0064] Compounds 2-11 were all pre...

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Abstract

The invention provides a chromone-containing benzimidazole bifurazan compound with a Cy-FBP / SBPase inhibition effect and a preparation method of the chromone-containing benzimidazole bifurazan compound. The molecular structure of the compound is shown as a formula I, wherein R is selected from hydrogen, halogen, nitro, hydroxyl, carboxyl or C1-C4 alkyl. On the basis, the invention further discloses a preparation method of the compound. The preparation method comprises the following steps of: firstly, synthesizing an intermediate 4-amino-1, 2, 5-oxadiazole-3-methoxyamidine by taking malononitrile as an initial raw material; synthesizing an intermediate 3-(2-(4-amino-1, 2, 5-oxadiazole-3-)-1H-benzo [d] imidazole-1-) propanohydrazide by taking o-phenylenediamine as an initial raw material; and finally carrying out aldehyde-hydrazine condensation reaction on the intermediates and 3-formylchromone or substitutes thereof so as to generate the chromone-containing benzimidazole bifurazan compound of the invention. The compound of the invention has a good inhibition effect on Cy-FBP / SBPase; the IC50 value of the compound is within the range of 5.36-36.61 microns; and the compounds can be used for inhibiting growth of blue-green algae or preparing related algistat.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a chromone-containing benzimidazole bifurazan compound with Cy-FBP / SBPase inhibitory effect and a preparation method thereof. Background technique [0002] In recent years, with the expansion of human life and production activities, a large amount of waste water has been discharged into rivers and lakes, the eutrophication of water bodies has become increasingly serious, and blue-green algae have exploded and reproduced, forming algal blooms. After the cyanobacteria die, they will release algal toxins, which are very stable, water-soluble and heat-resistant. Algae toxins are not easy to decompose when boiled in water at high temperature, and general tap water treatment processes (such as coagulation sedimentation, filtration, and chlorine addition) cannot decompose it. Algae toxin is a strong cancer-promoting agent, which can cause liver cancer. It is very toxic and a...

Claims

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Application Information

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IPC IPC(8): C07D413/14A01N43/82A01P13/00
CPCC07D413/14A01N43/82
Inventor 涂其冬宋伏冰刘米米王莹周庭辉郭辉陈道驹向鹏李琪陈凤
Owner JIANGXI SCI & TECH NORMAL UNIV
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