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C3-substituted tetrahydroisoquinoline derivative and preparation method and application thereof

A technology of tetrahydroisoquinoline and derivatives, which can be used in drug combinations, blood diseases, extracellular fluid diseases, etc., can solve problems such as treatment cost burden, and achieve the effects of good biological activity, novel structure and simple preparation method.

Inactive Publication Date: 2017-06-13
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no cure for this type of disease on the market, and it can only alleviate the disease when it occurs, (Chinese Journal of Lung Diseases (Electronic Edition). 2014, 5, 573). Therefore, the cost of treatment also brings an economic burden to patients.

Method used

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  • C3-substituted tetrahydroisoquinoline derivative and preparation method and application thereof
  • C3-substituted tetrahydroisoquinoline derivative and preparation method and application thereof
  • C3-substituted tetrahydroisoquinoline derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0066] Example 1: 7-cyclopentyloxy-8-methoxy-1,5,10,10a-tetrahydro-2-p-trifluoromethoxybenzoyl[3,4-b]isoquinoline- Preparation of ethyl 3-formate (5)

[0067] Using vanillin as a starting material, undergo substitution, addition elimination, reduction, acylation, Bischler-Napieralski reaction and acylation reaction to obtain tetrahydroisoquinoline and carbamate compounds. The preparation process is as follows:

[0068]

[0069] Reagents and conditions: a.K 2 CO 3 ,DMF; b.NO 2 CH 2 COOEt, (CH 3 ) 2 NH·HCl, KF; c.H 2 ,10%Pd / C; d.HCOOH,EDC,DMAP; e.I.POCl 3 , toluene; II.H 2 , 10% Pd / C, MeOH, EtOAc; f.dry CH 2 Cl 2 ,Et 3 N, DMAP; g MeONa / MeOH; h 4N NaOH, THF / MeOH; I K 2 CO 3 , n-PentylBr, DMF; j EDC-HCl, DMAP, CH 2 Cl 2

[0070] (1) Preparation of 4-cyclopentyloxy-3-methoxybenzaldehyde (I-A)

[0071] Dissolve (25g, 0.164mol) vanillin in 80mL DMF, add (33g, 0.239mol) potassium carbonate solid, stir at room temperature for half an hour, then add (22mL, 0.193mol)...

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PUM

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Abstract

The invention discloses a C3-substituted tetrahydroisoquinoline derivative. A structure formula of the derivative is shown in formula I or formula II, wherein an R1 group is hydrogen, a naphthenic group, an alkyl group, a phenyl group or a substituted phenyl group; an R2 group is hydrogen or an alkyl group; a R3 group is an alkyl group; the substituted group is an alkyl group with 1 to 3 carbon atoms. The invention also provides a preparation method of the derivative and application in preparing phosphodiesterase II inhibitors. The preparation method comprises the following steps of using vanilline as raw material, and sequentially performing substituting reaction, addition and elimination reaction, reduction reaction, condensation reaction, Bischler-Napieralski reaction, acylation reaction, hydrolysis reaction and amidation reaction, so as to obtain the derivative. The derivative has stronger inhibition function on phosphodiesterase II, and has potential preventing and treatment effect on asthma and chronic pulmonary thromboembolism diseases.

Description

technical field [0001] The invention belongs to the technical field of preparation of heterocyclic compounds, and more specifically relates to a C3-substituted tetrahydroisoquinoline derivative, a preparation method and application thereof. Background technique [0002] At present, there are about 300 million people suffering from asthma in the world, and the incidence rate is on the rise. (Journal of Clinical Medicine Literature. 2016, 22, 4513) Asthma is a chronic airway inflammatory disease that often occurs in childhood and is related to allergies and eosinophils. Chronic obstructive pneumonia is similar to asthma, but often occurs in middle age; (Journal of Difficult and Difficult Diseases. 2015, 7,759) The two have common clinical manifestations, but belong to two different diseases, (Chinese Journal of Respiratory and Critical Care. 2014, 2, 219 ) In 2014, relevant organizations proposed the concept of asthma-chronic obstructive pneumonia overlap syndrome (ACOS), but...

Claims

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Application Information

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IPC IPC(8): C07D217/26A61P11/06A61P11/00A61P7/02
CPCC07D217/26
Inventor 宋高鹏崔紫宁宋秀红崔志方蔡乃峻刘星宇
Owner SOUTH CHINA AGRI UNIV
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