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Coumarin skeleton based Wittig reagent as well as preparation method and application thereof

A coumarin skeleton and reagent technology, applied in the field of biochemistry, can solve the problems of relying on large analytical instruments, complex and cumbersome sample pretreatment process, etc., and achieve the effects of excellent selectivity and sensitivity, low overall cost and mild reaction conditions

Active Publication Date: 2018-09-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Currently, chromatography-mass spectrometry [4] It is widely used to detect DNA oxidative damage, but this method involves complex and cumbersome sample pretreatment process and relies on expensive large-scale analytical instruments

Method used

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  • Coumarin skeleton based Wittig reagent as well as preparation method and application thereof
  • Coumarin skeleton based Wittig reagent as well as preparation method and application thereof
  • Coumarin skeleton based Wittig reagent as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0034] The preparation method of the Wittig reagent based on coumarin skeleton comprises the following steps:

[0035] a. Dissolve R-substituted salicylaldehyde and ethyl acetoacetate in an organic solvent, add piperidine, and reflux for 4 to 12 hours to prepare intermediate 1; the molar weight of the ethyl acetoacetate is R-substituted salicyl 1.5 to 2.5 times that of aldehyde, and the molar weight of piperidine is 0.1 to 1.6 times that of R-substituted salicylaldehyde; the organic solvent is any one of absolute ethanol, isopropanol, acetonitrile or dichloromethane.

[0036] b. Dissolve intermediate 1 in glacial acetic acid, add liquid bromine and hydrobromic acid, and stir overnight at room temperature to prepare intermediate 2; the molar weight of the liquid bromine is 1.5 to 2.0 times that of intermediate 1, and the hydrogen The molar amount of bromic acid is 3 to 5 times that of intermediate 1.

[0037] c. Intermediate 2, Ph 3 P (triphenylphosphine), KI (potassium iodid...

Embodiment 1

[0044] Example 1 Synthesis of 3-acetyl-7-(diethylamino)coumarin (compound 1):

[0045]

[0046] 4-(Diethylamino)salicylaldehyde (1.93g, 10mmol), ethyl acetoacetate (1.85g, 15mmol), piperidine (1mL, 39.5mmol) were dissolved in 200mL absolute ethanol, and refluxed at 80°C. After the reaction was complete, it was cooled to room temperature, filtered with suction, washed with ice ethanol, and dried in vacuo to obtain 2.15 g (8.3 mmol) of a shiny yellow solid with a yield of 83%.

[0047] 1 H NMR (400MHz, CDCl 3 )δ8.43(s,1H),7.39(d,J=9.0Hz,1H),6.61(dd,J=9.0,2.4Hz,1H),6.46(d,J=2.3Hz,1H),3.45( q,J=7.1Hz, 4H), 2.67(s,3H), 1.24(t,J=7.1Hz,6H).

Embodiment 2

[0048] Example 2 Synthesis of 3-(2-bromoacetyl)-7-(diethylamino)coumarin (compound 2):

[0049]

[0050] Compound 1 (1.5g, 5.78mmol), 50% hydrobromic acid aqueous solution (2.8g, 17.3mmol) were dissolved in 150mL glacial acetic acid, and liquid bromine (1.48g, 9.25mmol) was added dropwise under stirring conditions, and the dropwise , stirred overnight at room temperature. The solvent was removed under reduced pressure at 70°C, 100ml of water was added, the pH was adjusted to 8-9 with saturated sodium bicarbonate solution, extracted three times with dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and spin-dried. Chloroform was recrystallized to obtain 1.29 g (3.81 mmol) of an orange solid with a yield of 66%.

[0051] 1 H NMR (400MHz, CDCl 3 )δ8.53(s,1H),7.43(d,J=9.0Hz,1H),6.64(dd,J=9.0,2.5Hz,1H),6.48(d,J=2.4Hz,1H),4.77( s, 2H), 3.48 (q, J = 7.2Hz, 4H), 1.25 (t, J = 7.1Hz, 6H).

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Abstract

The invention belongs to the field of biochemistry and mainly relates to a coumarin skeleton based Wittig reagent as well as a preparation method and application thereof. The Wittig reagent disclosedby the invention is based on coumarin skeleton improvement, and a structural formula of the reagent is shown as a formula I. In addition, the invention further provides a preparation method of the compound and application thereof in a nucleic acid detection aspect. According to the coumarin skeleton based Wittig reagent designed in the invention, in an effective combination of a fluorescence sensing technology and a traditional Wittig reaction, high-sensitivity high-selectivity detection of 5-formyl uracil (5fU) is realized. Meanwhile, the reagent is simple in synthetic route, mild in reactionconditions and economic and readily available in raw materials, and provides a new thought for designing the conventional reactive 5-formyl uracil (5fU) fluorescence probe.

Description

technical field [0001] The invention belongs to the field of biochemistry, and in particular relates to a Wittig reagent based on a coumarin skeleton and a preparation method and application thereof. Background technique [0002] DNA damage is ubiquitous in cells [1] . 5-formyl uracil (5fU) is a kind of oxidative damage to DNA with a content comparable to that of 8-hydroxydeoxyguanosine (8-oxodGuo), which is obtained from thymine (T) through a series of oxidation processes [2] . Endogenous reactive oxygen species (ROS) in cells, exogenous ultraviolet radiation, ion radiation, Fenton's reagent, etc. will all increase the content of 5fU in cells. Compared with thymine with a methyl group at the C-5 position, 5-formyluracil (5fU) with an aldehyde group at the C-5 position has a significantly stronger acidity at the N-3 position, and it is easy to deprotonate and exist in an ionized form. The ionized form is easy to form mismatches with G, C, and T in the process of DNA repl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655C09K11/06G01N21/64
CPCC07F9/65522C09K11/06C09K2211/1007C09K2211/1088G01N21/6486
Inventor 余孝其李坤周倩
Owner SICHUAN UNIV
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