Corynantheine compound and preparation method thereof

A technology of conanne bases and analogues, applied in the field of conanne base compounds and their preparation, to achieve the effects of high yield, convenient mass production, and good stability

Inactive Publication Date: 2014-05-21
FUDAN UNIV
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Problems solved by technology

In recent years, studies on alkaloids in Uncaria have shown that such alkaloids have the characteristics of high efficiency and low toxici...

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  • Corynantheine compound and preparation method thereof
  • Corynantheine compound and preparation method thereof
  • Corynantheine compound and preparation method thereof

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Embodiment Construction

[0038] 1: Chemical synthesis and preparation

[0039] All solvents, raw materials and reagents used in the present invention are analytically pure or chemically pure unless otherwise specified; the anhydrous treatment of solvents is carried out according to conventional methods.

[0040] Instruments and methods for product separation and identification: Thin-layer chromatography silica gel GF 254 , column chromatography coarse-pore silica gel (200-300 mesh), all produced by Qingdao Ocean Chemical Factory; TLC was detected by 154nm ultraviolet; NMR was measured by Varian VXR-500 NMR instrument, hydrogen spectrum, carbon spectrum with TMS as internal standard .

[0041] 1.1 Synthesis of 1-ethoxycarbonylmethyl-1,2,3,4-tetrahydrocarboline (Formula 2)

[0042] In a 500ml round bottom flask, add 200ml of dichloromethane dissolved with 8g (50mmol) of tryptamine and 30ml of ethyl 3,3-diethoxypropionate successively, and then slowly add 12ml of trifluoroacetic acid dropwise under sti...

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Abstract

The invention belongs to the field of medicines and relates to a corynantheine compound and a preparation method thereof. The corynantheine compound has a structure as shown in formulas (1) and (2). The preparation method comprises the step: with tryptamine as an initial raw material, carrying out Pictet-Spengler reaction, butyl lithium aluminum hydride reduction, cascade reaction of Knoevenagel/hetero-Diels+/-Alder, hydrogenation reaction and other multi-step reactions to obtain a corynantheine analogue with the general formulas (1) and (2). The corynantheine analogue disclosed by the invention is a novel compound with direct vasodilative activity and has the advantages of simple and convenient synthesis method, easiness for control, high synthesized product quantity, high purity and the like; the prepared corynantheine compound is good in self-stability and wide in modification range, can be used for preparing a candidate drug for dilating peripheral vessels and treating hypertension, and can be used as a potential pharmacological tool.

Description

technical field [0001] The invention belongs to the field of medicine, and relates to conanin base compounds and a preparation method thereof. The present invention uses tryptamine as a starting material, and through multi-step reactions, synthesizes conanine analogues and derivatives thereof; the preparation method has the advantages of strong operability, simple reaction conditions, easy control, and high product purity; The obtained product has good self-stability, can be used to prepare antihypertensive drug candidates for expanding peripheral blood vessels, and can be used as a potential pharmacological tool. Background technique [0002] Uncaria (Ucaria) is a traditional Chinese medicine for lowering blood pressure. After research, its main antihypertensive component is the alkaloid it contains. In recent years, studies on alkaloids in Uncaria have shown that such alkaloids have the characteristics of high efficiency and low toxicity, and corynantheine is one of the a...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D471/14A61P9/08A61P9/12
CPCC07D471/04C07D471/14
Inventor 朱依谆鲍光植古险峰朱依纯
Owner FUDAN UNIV
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