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Long wavelength emitting chemiluminescent probes

A compound, straight-chain technology, applied in the compound of Ib and II, in the field of formula Ia, can solve the problems of complex synthesis, easy solubility, trouble and the like

Inactive Publication Date: 2021-03-09
尼米斯技术公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These probes are based on 4-(dicyanomethylene)-4H-chromen-2-yl and 5,5-dimethyl-3-cyano-2-dicyanomethylene-2,5- Dihydrofuran-4-yl substituents, which act as π acceptors and shift the luminescence to long wavelengths, however, this makes their synthesis rather complicated and cumbersome
Furthermore, these substituents are quite hydrophobic, making these probes prone to solubility issues in aqueous media
Therefore, if used for in vitro or in vivo imaging, these probes must also have solubility-enhancing substituents (e.g., acrylic acid substituents), however, making their synthesis even more complicated

Method used

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  • Long wavelength emitting chemiluminescent probes
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  • Long wavelength emitting chemiluminescent probes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0433] General method:

[0434] All reactions were performed at room temperature unless otherwise stated. Chemicals and solvents were A.R. grade or purified by standard techniques. Thin Layer Chromatography (TLC): Silica gel plates Merck 60F254: Compounds were visualized by irradiation with UV light. Column chromatography (FC): silica gel Merck 60 (particle size 0.040-0.063 mm), eluents are given in parentheses. Reverse-phase high-pressure liquid chromatography (RP-HPLC): C185μ, 250×4.6 mm, eluents are given in parentheses. Preparative RP-HPLC: C18 5μ, 250 x 21 mm, eluents are given in parentheses. Fluorescence and chemiluminescence were recorded on a Molecular Devices Spectramax i3x.

[0435] If not stated otherwise, all chemicals were purchased from Merck and Biosynth AG and used as received.

[0436] Abbreviation. AcOH-acetic acid, MeCN-acetonitrile, DCM-dichloromethane, DMF-N,N'-dimethylformamide, EtOAc-ethyl acetate, Hex-hexane, MeOH-methanol, TFA-trifluoroacetic aci...

Synthetic example 1

[0437] Synthesis Example 1: Synthesis of Exemplary Compounds

[0438] Synthesis was performed according to the following general scheme:

[0439]

[0440]

[0441]Aldehyde 1 (as described in "Chemiluminescent Probes for Activity-Based Sensing of Formaldehyde Released from Folate Degradation in Living Mice" (Angew. Chem. Int. Ed., 2018, Volume 130, Issue 25, Pages 7630-7634) was prepared; see Supplementary Information) (0.66 mmol, 220 mg) was dissolved in DMF (6.6 mL) and the solution was cooled to 0°C. Then add K 2 CO 3 (1.3eq., 0.86mmol, 120mg) and the reaction mixture was stirred at room temperature. Add iodide 2 (cf., Karton-Lifshin N., Albertazzi L., Bendikov M., Baran PS., Shabat D., J Am Chem Soc., 2012, 134(50), 20412-20) (1.3eq. , 0.86mmol, 296mg) and the reaction mixture was stirred at room temperature for 3h. By TLC (Hex / Et 2 O=9:1) to monitor the reaction. After completion, the mixture was cooled to 0 °C and washed with Et 2 Dilute with O (15 mL) and...

Synthetic example 2

[0448] Synthesis Example 2: Synthesis of Exemplary Compounds

[0449] Synthesis was performed according to the following general scheme:

[0450]

[0451] Compound 1 (1.5 mmol, 0.50 g) and 4-picoline (2) (1.53 mmol, 0.143 g) were placed in acetic anhydride and the mixture was stirred under reflux. After 6.5 h, the mixture was cooled to room temperature, MeOH (10 mL) and K 2 CO 3 And the resulting mixture was stirred at room temperature. After 2 h, the mixture was concentrated in vacuo and saturated NH 4 Aqueous Cl solution (20 mL). The resulting mixture was extracted with EtOAc (3 times, 20 mL), the combined organics were dried and concentrated in vacuo. The crude mixture was purified by column chromatography to yield compound 3 (0.256 g, 42%) as a yellow solid.

[0452] 1 H NMR (300MHz, CDCl 3 )δppm 1.20-2.40 (m, 13H), 3.28 (bs, 1H), 3.33 (s, 3H), 6.88 (d, J = 8.0Hz, 1H), 7.14 (d, J = 16.5Hz, 1H), 7.40 (bd, J=5.4Hz, 2H), 7.47 (dd, J=8.0Hz, 0.4Hz, 1H), 7.62 (d, J...

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PUM

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Abstract

The present invention relates to dioxetane compounds of Formula la or lb, a compound of Formula II and their applications.

Description

technical field [0001] The present invention relates to long wavelength emitting probes, in particular to compounds of formulas Ia, Ib and II and applications thereof. Background technique [0002] Optical imaging modalities have emerged as powerful tools for real-time, non-invasive observation of biomolecular systems and whole bodies (eg, animals or humans) with high spatial resolution. In addition, imaging systems are relatively inexpensive, easy to use, portable, and suitable for acquiring physiological and functional information from microscopic to macroscopic levels. [0003] There are several approaches to optical imaging, of which fluorescence is the most common. This technique is widely used to image and monitor various biological processes in vivo. However, in fluorescence techniques, complications arise due to auto-fluorescence and light interference which often add to the background noise. One way of overcoming this obstacle is to use bioluminescence technology...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D321/00C07F5/04
CPCC07D321/00C07F5/04C07D405/10C09K11/06C09K2211/1018G01N21/763G01N21/766G01N33/582
Inventor J·伊森U·斯皮茨D·沙巴特O·格林N·哈纳尼亚
Owner 尼米斯技术公司
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