A kind of spiropyran-naphthalimide derivative and its synthesis method and application

A technology of naphthalimide and synthesis method, applied in the field of spiropyran derivatives, can solve problems such as unexplained mechanism of action

Active Publication Date: 2021-05-14
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the mechanism of action at the molecular level has not yet been elucidated

Method used

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  • A kind of spiropyran-naphthalimide derivative and its synthesis method and application
  • A kind of spiropyran-naphthalimide derivative and its synthesis method and application
  • A kind of spiropyran-naphthalimide derivative and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Preparation and characterization of NSPs

[0053] Mix 2,3,3-trimethyl-3H-indole (3.18g, 20mmol) and 3-bromopropionic acid (6.08g, 40mmol) in 30mL of anhydrous acetonitrile, and heat the mixture at 85°C for 12 hours After the reaction was completed, the solvent was removed under reduced pressure, and the residue obtained was washed three times with 20 mL of ether to remove unreacted raw materials, and the residue was recrystallized with dichloromethane (5 mL) and acetone (25 mL) by volume to obtain a light purple powder product (3.78 g, produced rate: 57.7%). 1 H NMR(600MHz,DMSO)δ12.69(s,1H),7.99(d,J=4.3Hz,1H),7.85(d,J=4.0Hz,1H),7.65–7.59(m,2H),4.66 (t,J=6.8Hz,2H),2.99(t,J=6.9Hz,2H),2.86(s,3H),1.53(s,6H). 13 C NMR (151MHz, DMSO) δ198.40(s), 172.01(s), 142.23(s), 141.32(s), 129.82(s), 129.39(s), 123.95(s), 116.04(s), 54.73 (s), 43.99(s), 31.57(s), 22.34(s), 14.82(s).

[0054] 1-(2-carboxyethyl)-2,3,3-trimethyl-3H-indole-1-bromide (3.27g, 10mmol), 5-nitrosalicylaldehyd...

Embodiment 2

[0059] Prepare PBS buffer solution with pH=7.4 and concentration of 10mM, prepare 2mM NSP in DMSO solution, prepare 2mM hydrogen sulfide aqueous solution; take 2mL C 2 h 5 Add OH / PBS (v / v=1:1, pH=7.4) solution and 10 μL NSP DMSO solution to a fluorescent cuvette, take the aqueous solution of hydrogen sulfide, and gradually add it to the cuvette with a micro-injector In the process, it was detected on a spectrophotometer while adding the sample. With the addition of hydrogen sulfide, the fluorescence intensity at 540nm gradually increased. Fluorescence emission map see Figure 4 .

Embodiment 3

[0061] Prepare PBS buffer solution with pH=7.4 and concentration of 10mM, prepare 2mM NSP in DMSO solution, prepare 2mM hydrogen sulfide aqueous solution; add 2mL of C 2 h 5 OH / PBS (v / v=1:1, pH=7.4) solution and 10 μL NSP in DMSO solution, then add 10 times the equivalent of other analytes and hydrogen sulfide: NSP, Cys, Hcy, GSH, SO 4 2- ,SCN - ,S 2 o 3 2- ,S 2 o 5 2- ,AcO - ,CO 3 2- ,NO 3 - , SO 3 2- ,S 2- , the aqueous solution is detected on a fluorescence spectrophotometer, and the fluorescence intensity histogram at 540nm corresponding to different analytes is drawn (see Figure 5 ). Hydrogen sulfide significantly increases the fluorescence intensity of the detection system at 540 nm, and other analytes basically do not cause changes in the fluorescence intensity of the detection system.

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Abstract

The invention provides a spiropyran-naphthalimide derivative and its synthesis method and application, the Chinese name of the derivative is N-(2-(6-azido-1,3-dioxo ‑1H‑benzo[de]isoquinoline‑2(3H)‑yl)ethyl)‑3‑(3',3'‑dimethyl‑6‑nitrospiro[chromene‑2,2'‑ Dihydroindoline]‑1'‑yl) propionamide, the English name is N‑(2‑(6‑azido‑1,3‑dioxo‑1H‑benzo[de]isoquinolin‑2(3H)‑yl)ethyl) ‑3‑(3',3'‑dimethyl‑6‑nitrospiro[chromene‑2,2'‑indolin]‑1'‑yl)propanamide, named NSP, which can be converted to its isomer by UV irradiation Bulk NMR. Assay method is in PBS‑C pH 7.4 2 h 5 In the buffer solution of OH (1:1, v / v), the contents of hydrogen sulfide and sulfur dioxide were quantitatively detected by fluorescence spectrophotometer, respectively. The detection process is simple, sensitive and fast, and the detection result is accurate.

Description

technical field [0001] The invention relates to a spiropyran derivative, in particular to a spiropyran-naphthalimide derivative and a synthesis method thereof, and the application of the derivative in distinguishing and detecting hydrogen sulfide and sulfur dioxide. Background technique [0002] Reactive sulfides (RSS) in organisms include sulfur dioxide (SO 2 ), hydrogen sulfide (H 2 S), biothiols (Cys, Hcy and GSH) and polysulfides (RS-SH), etc. Endogenous hydrogen sulfide has been proved to be related to many physiological and pathological processes, such as regulation of vascular tone, myocardial contraction, nerve conduction and insulin secretion, etc. Abnormal concentrations of hydrogen sulfide in cells can cause diseases such as arterial and pulmonary hypertension, Alzheimer's disease, gastric mucosal damage, and liver cirrhosis. However, the mechanism of action at the molecular level has not been elucidated so far. In addition, biomedical studies have shown that ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643
Inventor 张伟杰阴彩霞霍方俊
Owner SHANXI UNIV
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