Coumarin-dithiocarbamate derivative and synthesizing method thereof

A synthetic method and dimethylformamide technology, applied in the field of coumarin-dithiocarbamate derivatives and their synthesis, can solve the problem of undiscovered coumarin-dithiocarbamate derivatives The synthetic method cannot fundamentally improve the disease state, terminate the disease and other problems, and achieve the effect of easy operation, high yield and stable quality of the synthetic method

Active Publication Date: 2018-01-19
广西壮族自治区肿瘤防治研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these drugs can relieve AD symptoms, they cannot fundamentally improve the disease state or stop the disease process
However, there are no relevant reports on coumarin-dithiocarbamate derivatives and their synthesis methods and their application in the treatment of AD.

Method used

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  • Coumarin-dithiocarbamate derivative and synthesizing method thereof
  • Coumarin-dithiocarbamate derivative and synthesizing method thereof
  • Coumarin-dithiocarbamate derivative and synthesizing method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0050] Embodiment 1: the preparation of intermediate 2 (7-hydroxyl-4-methylcoumarin)

[0051] Measure 15ml of dioxane (which can also be methanol or ethanol), add resorcinol (10mmol, 1.1g) to it, and add 4ml of concentrated sulfuric acid dropwise under ice bath conditions. Add ethyl acetoacetate (10mmol, 1.3g) into the solution, stir and heat to 60°C, and react for 4h. Recrystallized from methanol to obtain white needle-like solid crystals with a yield of 91%. 1 H NMR (600MHz, acetone-d 6 )δ7.61 (1H, d, J = 9.0Hz), 6.85 (1H, dd, J = 9.0, 2.5Hz), 6.75 (1H, d, J = 2.5Hz), 6.09 (1H, s), 2.40 ( 3H,s).ESI-MS m / z:175.0[M-H] - .

Embodiment 2

[0052] Example 2: General procedure for the preparation of intermediates 3a-f

[0053] Add 5.0mmol of intermediate 2 and 50mmol of dibromoalkane while stirring in acetone (also can be DMF, acetonitrile or tetrahydrofuran), and then add anhydrous K 2 CO 3 (1.4g, 10mmol) to adjust the pH of the system to 9-11, react at room temperature for 4 hours, then filter with suction after cooling, collect the filter residue, and purify the filter residue through a silica gel column (petroleum ether:ethyl acetate=15:1, volume ratio) , finally affording 3a-f as white solids.

Embodiment 3

[0054] Embodiment 3: The yield of intermediate 7-(8-bromoethoxy)-4-methylcoumarin (3a), NMR data and mass spectrometry data

[0055] Yield 86%; 1 H NMR (600MHz, CDCl 3 )δ7.53(d, J=8.8Hz, 1H), 6.91(dd, J=8.8, 2.5Hz, 1H), 6.83(d, J=2.5Hz, 1H), 6.17(s, 1H), 4.37( t,J=6.1Hz,2H),3.70(t,J=6.1Hz,2H),2.40(s,3H); ESI-MS m / z:283.1[M+H] + .

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Abstract

The invention discloses a coumarin-dithiocarbamate derivative and a synthesizing method thereof. The synthesizing method of the derivative comprises the following steps: 1) utilizing concentrated sulfuric acid as a catalyst, taking resorcinol and ethyl acetoacetate and putting into a first organic solvent to react to obtain an intermediate 2; 2) taking the intermediate 2 and dibromoalkane, puttinginto a second organic solvent and performing reaction under the condition that a pH is larger than or equal to 8 to obtain an intermediate 3; 3) taking the intermediate 3, carbon disulfide and secondary amine, putting into a third organic solvent and performing reaction under the condition that a pH is larger than or equal to 8 to obtain a corresponding target compound crude product. The synthesizing method disclosed by the invention has the advantages of simpleness and easiness in operation, high yield and stable quality; the synthesized coumarin-dithiocarbamate derivative has better acetylcholine esterase inhibiting activity; a lead compound is provided for developing novel AD treating medicine.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a coumarin-dithiocarbamate derivative and a synthesis method thereof. Background technique [0002] Alzheimer's disease (AD), also known as senile dementia, is a common neurodegenerative disease in the elderly. With the advent of an aging society, the problem of dementia is becoming more and more serious. Current drugs for the treatment of AD mainly rely on acetylcholinesterase (AChE) inhibitors (donepezil, galantamine, rivastigmine) and N-methyl-D-aspartate (NMDA) receptor antagonists (memantine) . Although these drugs can alleviate AD symptoms, they cannot fundamentally improve the disease state or terminate the disease process. [0003] Alzheimer's disease has a complex pathogenic mechanism. Although the pathogenesis of Alzheimer's disease is not fully understood, multiple interacting factors have been identified to be involved in the onset and progression of the disease....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C07D405/12A61P25/28
Inventor 蒋能梁宁生谢赛赛黄其春张小英潘文李艳雷宇
Owner 广西壮族自治区肿瘤防治研究所
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