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Six-ring indole alkaloid and preparation method thereof

A compound and C1-C12 technology, applied in the field of hexacyclic indole alkaloids and their preparation, can solve the problems of single product, destruction of ecology, low yield and the like

Inactive Publication Date: 2013-04-10
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Indole alkaloids A, B, and C are derived from the leaves of natural plants. However, the extraction of these compounds by this method is limited by the characteristics of low yield, single product, and ecological destruction.

Method used

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  • Six-ring indole alkaloid and preparation method thereof
  • Six-ring indole alkaloid and preparation method thereof
  • Six-ring indole alkaloid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1. Preparation of six-ring indole alkaloids of formula VII (as shown in formula (33))

[0073]

[0074] 1) Dissolve 1.82 g of the compound represented by formula (28) (corresponding to the compound represented by formula II) in 200 mL of ether, and slowly add 6.26 mL of a strong basic compound of tert-butyl lithium in n-pentane solution in an inert atmosphere at -40°C (In this system, the molar ratio of the compound represented by formula (28) to tert-butyl lithium is 1.0:3.0), the reaction is stirred at -40°C for 0.5 hours and then moved to room temperature and 25°C for 1 hour; add to the system 0.25mL of secondary water, followed by 0.82g of compound b paraformaldehyde (the compound represented by formula (28) in the system, the molar ratio of secondary water to paraformaldehyde with a molecular weight of 303.0g / mol is 1.0:5.0: 10.0), the reaction was stirred at room temperature and 25°C for 2.5 hours. The reaction was quenched by adding water twice, extracted wi...

Embodiment 2

[0079] Example 2. Preparation of compound represented by formula VIII, formula (34)

[0080]

[0081] 1) 0.06 g of the compound represented by formula (33) prepared in Example 1 was dissolved in 2 mL of tetrahydrofuran, and added to 30 mL of liquid ammonia, and the reaction was carried out in a nitrogen atmosphere at -76°C. 0.055 g of sodium (the molar ratio of the compound represented by formula (33) to sodium in the system is 1.0:23.5) was added to the above system part by part until a blue solution was formed, and the reaction was stirred for 15 minutes. The reaction was quenched with solid ammonium chloride, heated to room temperature to volatilize ammonia gas, added twice with water, extracted with dichloromethane (4x10mL), and the organic phase was washed with MgSO 4 It is dried, filtered, concentrated, and purified by flash chromatography to obtain 0.031 g of the compound represented by formula (34) (that is, the compound represented by formula VIII) (yield 68%). Brown sol...

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Abstract

The present invention discloses a six-ring indole alkaloid and a preparation method thereof. The six-ring indole alkaloid is shown in formula I. The method provided by the invention is simple in preparation steps, cheap in raw materials, mild in reaction conditions, high in yield, simple in operation, easy to amplify, and easy to derive the product, and has large potential for industrial production.

Description

Technical field [0001] The invention relates to a six-ring indole alkaloid and a preparation method thereof. Background technique [0002] In 2010, Hao Xiaojiang’s research team extracted a class of indole alkaloids (A1), (B2) and (C3) with new carbon skeleton compounds from the leaves of Trigonostemon Lii collected in Yunnan, China. Trigonoliimines A, B and C) (Org. Lett. 2010, 12, 2370-2373). The biological activity test of indole alkaloids A and C showed that: A showed strong anti-AIDS activity (EC50=0.95μg / mL, TI=7.9), its biological activity and the activity of clinical drug AZT (EC50=0.02μg) / mL, TI=59924) is similar. The same test C did not show any activity, and there is no relevant test information for B activity in the original report. The change and adjustment of the small structure can cause huge differences in the activity of such alkaloids, so its research and transformation is expected to be used as a lead compound for the development of new anti-AIDS clinical d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C07F7/10
Inventor 史一安冯鹏举范玉凯
Owner INST OF CHEM CHINESE ACAD OF SCI
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