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(1Z, 4Z, 5Z) ¿C 6 N alkyl ¿C 6 ¿C aza ¿C2 ¿C oxo ¿C 3 ¿C oxa ¿C 4 ¿C methoxy ¿C dicyclo [3, 1, 0] hexane and preparation method

An aziridine and methoxy technology, applied in (1Z,4Z,5Z)-6-N-alkyl-6-aza-2-oxo-3-oxa-4-methoxy - Bicyclo[3.1.0]hexane and its preparation and application fields, can solve the problems of low yield and no anticancer activity, and achieve the effects of reducing cost, improving yield and simplifying experimental operation

Inactive Publication Date: 2007-12-26
BEIJING NORMAL UNIVERSITY
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

As in Document 1: Li Senlan, Guo Jinbo, Yu Zhaolian, Chen Qinghua Chinese Chemistry 2004, 22 (4), 384 discloses a kind of use of 5-methoxy-3-bromo-2 (5H)-furanone as raw material, in A method of synthesizing racemic aziridine derivatives by reacting with primary amines under phase transfer catalysis conditions, but the yield of this method is low, only one of the enantiomers can be obtained and there is no anticancer activity

Method used

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  • (1Z, 4Z, 5Z) ¿C 6 N alkyl ¿C 6 ¿C aza ¿C2 ¿C oxo ¿C 3 ¿C oxa ¿C 4 ¿C methoxy ¿C dicyclo [3, 1, 0] hexane and preparation method
  • (1Z, 4Z, 5Z) ¿C 6 N alkyl ¿C 6 ¿C aza ¿C2 ¿C oxo ¿C 3 ¿C oxa ¿C 4 ¿C methoxy ¿C dicyclo [3, 1, 0] hexane and preparation method
  • (1Z, 4Z, 5Z) ¿C 6 N alkyl ¿C 6 ¿C aza ¿C2 ¿C oxo ¿C 3 ¿C oxa ¿C 4 ¿C methoxy ¿C dicyclo [3, 1, 0] hexane and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] The synthesis of embodiment 1, hydroxybutene lactone (compound 2)

[0037] Dissolve 236g (2.46mol) of freshly steamed furfural (compound 1) in 2300mL of 95% ethanol, add 2g of rose bengal (Rose Bengal) as a photosensitizer, pass in oxygen, irradiate with a 1000W iodine tungsten lamp, and keep the temperature at 23-27 ℃, magnetic stirring, TLC (thin layer chromatography) tracking reaction, the reaction takes about 40h; after the reaction is stopped, the ethanol is evaporated on a rotary evaporator to obtain a wine-red thick liquid, and a yellow solid is precipitated after freezing, which is quickly filtered by suction , dried to give a light yellow solid; recrystallized from petroleum ether to obtain hydroxybutenolactone (compound 2), 158 g of white needle-like crystals, yield 64%, m.p.54-55°C.

Embodiment 2

[0038] The synthesis of embodiment 2,5-methoxyl group-2(5H)-furanone (compound 3)

[0039] Dissolve 20g (200mmol) of hydroxybutene lactone (compound 2) in 80mL of methanol, heat to reflux in an oil bath (about 72h), and track the reaction by TLC; after the reaction, remove methanol by rotary evaporation on a rotary evaporator to obtain crude product ; Distillation under reduced pressure or flash column chromatography (petroleum ether / acetone=20:1) to obtain 5-methoxy-2(5H)-furanone (compound 3), colorless liquid, 16g, yield 70%.

Embodiment 3

[0040] Embodiment 3, the synthesis of 5-methoxy-3-bromo-2 (5H)-furanone (compound 4)

[0041] Dissolve 16g (140.4mmol) of 5-methoxy-2(5H)-furanone (compound 3) in 140mL of benzene, then slowly add Br 2 , stir evenly at room temperature, cool the ice-water bath to 0°C, and slowly add pyridine dropwise. After the addition, remove the ice-water bath, stir at room temperature, and react for about 1.5 hours; Dissolve, separate the organic layer, wash with saturated brine, then add anhydrous magnesium sulfate to dry; filter, evaporate the solvent under reduced pressure to obtain the crude product by vacuum distillation or flash column chromatography (petroleum ether / acetone=20:1) , to obtain 5-methoxy-3-bromo-2(5H)-furanone (compound 4), light yellow liquid, 20 g, yield 73.8%.

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Abstract

This invention relates to aziridine derivatives, i.e., (1Z, 4Z,5Z)-6-N-n-hexadecyl / octadecyl-6-aza-2-oxo-3-oxa-4-methoxy-bicyclo[3.1.0]hexane, as shown in chemical formulae I and II. This invention also provides a method for preparing the aziridine derivatives. The preparation method comprises: synthesizing 5-methoxy-3-bromo-2(5H)-furanone, reacting with hexadecylamine / octadecylamine, and Et3N in DMSO to obtain the aziridine derivatives. The aziridine derivatives have good inhibitive effects on colon cancer cells, human gastric cancer cells and human ovarian cancer cells, and can be used in drugs for treating colon cance, gastric cancer and ovarian cancer. The preparation method avoids traditional phase transfer catalysis and water / oxygen-free operation, and adopts room temperature homogeneous catalytic condition, thus has such advantages as simple operation, low cost and high target compound yield. Besides, another diasteromer can be obtained.

Description

technical field [0001] The present invention relates to an aziridine derivative, in particular to a (1Z, 4E, 5Z)-6-N-n-hexadecyl-6-aza2-oxo-3-oxa -4-methoxy-bicyclo[3.1.0]hexane, and (1Z,4E,5Z)-6-N-n-octadecyl-6-aza-2-oxo-3-oxa- 4-methoxy-bicyclo[3.1.0]hexane, its preparation method and use. Background technique [0002] Aziridine derivatives are an important class of compounds. Many natural products with physiological activity, such as mitomycin, porgiromycin, nitrogen serine, etc., contain components of aziridine structure. In order to study the structure and pharmacological relationship of these natural products, a series of model compounds of various aziridine derivatives containing quinone and ethyleneimine were synthesized. [0003] In addition, aziridine derivatives are an important class of organic synthesis intermediates, often used to synthesize alkaloids, amino acids, β-amino alcohols, β-lactams, pyrrolidine polymers, and chiral auxiliary reagents or chiral Li...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/048A61K31/396A61P35/00
Inventor 吴建平裴强周东新何兰石建功赵和平
Owner BEIJING NORMAL UNIVERSITY
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