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A kind of total synthesis method of amide alkaloid

A technology of alkaloids and amides, which is applied in the field of total synthesis of amide alkaloids, can solve the problems of unsatisfactory research needs, limited sources of Taibai Aconitum, high cost requirements, etc., to overcome the cumbersome extraction and separation process, high yield, Simple and easy to operate effect

Active Publication Date: 2017-02-01
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Based on its good activity, our research group plans to conduct in-depth research on it, but the source of Taibai Aconitum is limited, and the separation is cumbersome, the cost is high, and the cycle is long, which cannot meet the needs of research.

Method used

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  • A kind of total synthesis method of amide alkaloid
  • A kind of total synthesis method of amide alkaloid
  • A kind of total synthesis method of amide alkaloid

Examples

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Embodiment 1

[0038] The total synthesis method of 3-isopropyl-tetrahydropyrrole [1,2-a] pyrimidine-2,4 (1H, 3H)-dione comprises the following steps:

[0039] 1. Preparation of diethyl isopropylmalonate

[0040] Sodium ethoxide (5.61g, 82.5mmoL) was dissolved in 80mL of absolute ethanol, and diethyl malonate (12g, 75mmoL) was added dropwise thereto under constant stirring, and after the addition was completed, the temperature was raised and refluxed for 2 hours; the temperature was lowered and stirred continuously Isopropyl bromide (13.84 g, 112.5 mmol) was added dropwise, and after the addition was completed, the temperature was raised and the mixture was refluxed for 6 hours. TLC tracking, after the completion of the reaction, the temperature was lowered, filtered with suction, and the filtrate was collected. The pH was adjusted down to 5-6 in ice bath, and the solvent was removed by rotary evaporation. Dissolve in 100mL ethyl acetate, wash with 100mL saturated sodium chloride three tim...

Embodiment 2

[0055] The total synthesis method of 3-tert-butyl-tetrahydropyrrole [1,2-a] pyrimidine-2,4 (1H, 3H)-dione comprises the following steps:

[0056] 1. Preparation of diethyl tert-butylmalonate

[0057] Sodium ethoxide (5.61g, 82.5mmoL) was dissolved in 80mL of absolute ethanol, and diethyl malonate (12g, 75mmoL) was added dropwise thereto under constant stirring, and after the addition was completed, the temperature was raised and refluxed for 2 hours; the temperature was lowered and stirred continuously Bromo-tert-butane (15.41 g, 112.5 mmol) was added dropwise, and after the dropwise addition was completed, the temperature was raised and the mixture was refluxed for 6 hours. TLC tracking, after the completion of the reaction, the temperature was lowered, filtered with suction, and the filtrate was collected. The pH was adjusted down to 5-6 in ice bath, and the solvent was removed by rotary evaporation. Dissolve in 100mL ethyl acetate, wash with 100mL saturated sodium chlorid...

Embodiment 3

[0063] The total synthesis method of 3-cyclopropyl-tetrahydropyrrole [1,2-a] pyrimidine-2,4 (1H, 3H)-dione comprises the following steps:

[0064] 1. Preparation of dimethyl cyclopropylmalonate

[0065] Sodium ethoxide (5.61g, 82.5mmoL) was dissolved in 80mL absolute ethanol, and dimethyl malonate (9.9g, 75mmoL) was added dropwise thereto under constant stirring, and the temperature was raised and refluxed for 2 hours after the dropwise addition; Bromocyclopropane (13.61 g, 112.5 mmol) was added dropwise with stirring, and after the dropwise addition was completed, the temperature was raised and the mixture was refluxed for 6 hours. TLC tracking, after the completion of the reaction, the temperature was lowered, filtered with suction, and the filtrate was collected. The pH was adjusted down to 5-6 in ice bath, and the solvent was removed by rotary evaporation. Dissolve in 100mL ethyl acetate, wash with 100mL saturated sodium chloride three times, combine the organic phases, ...

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Abstract

The invention discloses a total synthesis method of amides alkaloid, and belongs to the technical field of the chemistry of natural products. The total synthesis method comprises the following steps: carrying out the synthesis by adopting malonate and 2-bromopropane or 2-bromopropane derivative as raw materials, thereby obtaining isopropyl malonate; (2) carrying out the synthesis by adopting 2-aminopyrrolidine as a raw material, thereby obtaining mid-body 2-amino tetralin pyrrolidine; and (3) synthesizing amides alkaloid 3-isopropyl-nafoxidine[1,2-alpha]pyrimidine-2,4(1H,3H)-diketone and a derivative by adopting the isopropyl malonate and the 2-2-amino tetralin pyrrolidine as a raw material. By adopting the total synthesis method, the defect that the extraction separation process in the natural product is complicated and the yield is low can be overcome, and the demand of perople for further researching the natural product can be satisfied; moreover, the synthesis method is simple in route, raw materials are cheap and easy to obtain, and the yield is relatively high.

Description

technical field [0001] The invention belongs to the technical field of natural product chemistry, and relates to a method for the total synthesis of amide alkaloids, in particular to 3-isopropyl-tetrahydropyrrole[1,2-a]pyrimidine-2,4(1H,3H)- Total synthesis of diketones and their derivatives. Background technique [0002] 3-Isopropyl-tetrahydropyrrole[1,2-a]pyrimidine-2,4(1H,3H)-dione is extracted and isolated from Taibai Aconitum, a unique plant of the genus Aconitum in Taibai County, Shaanxi Province, my country A kind of novel small molecular amide alkaloid obtained, structural formula is as follows: [0003] [0004] It is reported that amide alkaloids have a unique effect on anti-leukemia. Our research group chose human promyelocytic leukemia cell line HL-60 and human erythroleukemia cell line K562 to study the inhibition of this small molecule amide alkaloid The results show that: 3-isopropyl-tetrahydropyrrole[1,2-a]pyrimidine-2,4(1H,3H)-dione has a good inhibitory...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 郭增军李丹丹张杰张卉刘霞李梦怡席可
Owner XI AN JIAOTONG UNIV
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