Rofecoxib-like derivative, prepared organic fluorescent dye skeleton and application

A technology of rofecoxib and its derivatives, which is applied in the field of biological imaging and the field of organic fluorescent dye skeletons, can solve the problems of inability to meet the needs of analysis and detection, different photophysical and photochemical properties, and achieve improved photophysical and photochemical properties. Photochemical performance, improvement of photophysical and photochemical performance, effect of simple preparation method

Active Publication Date: 2021-02-09
FUJIAN INST OF MICROBIOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, people have made great achievements in the research of optical properties and biological imaging applications of organic fluorescent dyes and their derivatives. However, in most commercial organic fluorescent dyes that have been widely used, in terms of photophysical and photochemical properties There are different defects, which can no longer meet the needs of current chemical biology research and complex system analysis and detection

Method used

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  • Rofecoxib-like derivative, prepared organic fluorescent dye skeleton and application
  • Rofecoxib-like derivative, prepared organic fluorescent dye skeleton and application
  • Rofecoxib-like derivative, prepared organic fluorescent dye skeleton and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1: Compound 2a1((5Z)-5-(4-cyanobenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one )

[0057]

[0058] Add 0.12 g (0.0014 mol) of piperidine dropwise to 0.4 g (0.0013 mol) of compound 1a or 1b and 0.0026 mol of aromatic aldehyde in methanol mixed solution, react at room temperature and stir in a dark room for 12 hours, and the reaction solution reacts after detection After completion, after cooling and suction filtration, and washing with methanol, 0.28 g (89%) of the product was obtained as light yellow solid powder.

[0059] The nuclear magnetic data of gained compound is: 1 H-NMR (400MHz, DMSO-d 6 )δ8.04(d, J=8.5Hz, 2H), 7.96(d, J=8.6Hz, 2H), 7.88(d, J=8.6Hz, 2H), 7.67(d, J=8.5Hz, 2H) ,7.35–7.31(m,5H),6.16(s,1H),3.28(s,3H). 13 C-NMR (101MHz, DMSO-d 6 )δ167.77,149.99,149.06,142.31,138.10,135.11,133.20,131.37,130.90,129.95,129.93,129.72,129.07,128.95,128.19,127.59, 119.23,111.32,111.12,43.78.HR-MS(ESI):calcd for C 25 h 17 NNaO 4 S:450....

Embodiment 2

[0060] Example 2: Compound 2a2 ((5Z)-5-(benzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one)

[0061]

[0062] The preparation steps of compound 2a2 in this example are the same as those in Example 1, using compound 1a as the starting material to synthesize a yellow powder, and the calculated product yield is 86%.

[0063] The nuclear magnetic data of gained compound is: 1 H-NMR (400MHz, DMSO-d 6 )δ8.04(d, J=8.7Hz, 2H), 7.79(d, J=7.4Hz, 2H), 7.67(d, J=8.8Hz, 2H), 7.47–7.39(m, 3H), 7.38– 7.27(m,2H), 6.06(s,1H),3.28(s,3H). 13 C-NMR (101MHz, DMSO-d 6 )δ168.12, 149.44, 147.98, 142.21, 135.46, 133.47, 131.02, 130.88, 129.87, 129.65, 129.51, 129.22, 129.02, 128.15, 126.28, 113.39, 43.79.HR-MS 24 h 18 NaO 4 S:425.0823([M+Na] + ), found: 425.0817. It can be seen that the structure of the product is correct.

Embodiment 3

[0064] Example 3: 2a3((5Z)-5-(4-methylsulfonylbenzylidene)-4-(4-(methylsulfonyl)phenyl)-3-phenylfuran-2(5H)-one )

[0065]

[0066] The preparation steps of compound 2a3 in this example are the same as in Example 1, using compound 1a as the starting material to synthesize a yellow powder, and the calculated product yield is 88%.

[0067] The nuclear magnetic data of gained compound is: 1 H-NMR (400MHz, DMSO-d 6 )δ8.09–8.00(m,4H),7.96 (d,J=8.5Hz,2H),7.68(d,J=8.5Hz,2H),7.39–7.25(m,5H),6.19(s,1H ),3.28(s,3H), 3.22(s,3H). 13 C-NMR (101MHz, DMSO-d 6 )δ167.86,149.90,149.12,142.30,140.78,138.35,135.14,131.42,130.92,129.73,129.70,129.11,129.08,128.97,128.19,127.99,127.97,127.55, 111.10,43.79.HR-MS(ESI):calcd for C 25 h 20 NaO 6 S 2 :503.0599([M+Na] + ), found: 503.0588. It can be seen that the structure of the product is correct.

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Abstract

The invention belongs to the technical field of biomedical materials, particularly relates to a rofecoxib-like derivative, and further discloses an organic fluorescent dye skeleton prepared from the rofecoxib-like derivative and application of the rofecoxib-like derivative in the field of biological imaging. According to the rofecoxib-like series derivative disclosed by the invention, one-step condensation modification is only carried out on the basis of a COX-2 inhibitor rofecoxib structure through a computational chemistry and quantum orbital theory speculation technology, and a plurality ofsmall molecular fluorescent dyes and COX-2 inhibitor fluorescent probes with clinical development prospects are synthesized by adopting a brand-new design strategy; on the basis of keeping the strongCOX-2 enzyme inhibition activity, the photophysical and photochemical properties of the fluorescent dye are effectively improved, the fluorescent dye shows excellent fluorescence properties, and a more ideal choice is provided for the design of the fluorescent dye and the probe in the future.

Description

technical field [0001] The invention belongs to the technical field of biomedical materials, and specifically relates to a rofecoxib-like derivative, and further discloses an organic fluorescent dye skeleton prepared by it, and its application in the field of biological imaging. Background technique [0002] Fluorescent dyes are an important branch of dye chemistry. Especially in recent decades, fluorescent dyes and their derivatives have made many breakthroughs in materials, biology and medicine, and have gradually become a key branch of dye chemistry. research direction. Among them, organic fluorescent dyes, as an important class of fluorescent dyes, have ever-changing structures. In essence, since the structure of organic fluorescent dyes usually includes a fluorescent parent nucleus and a chromophoric group that can change the fluorescence wavelength and enhance fluorescence, with the rapid development of analytical chemistry, biological science, life science and medici...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58C09K11/06C09B57/00G01N21/64
CPCC07D307/58C09K11/06C09B57/00G01N21/643C09K2211/1088C09K2211/1007G01N2021/6432G01N2021/6439G01N2021/6417Y02P20/55
Inventor 谢立君林风江红胡明谢作旭
Owner FUJIAN INST OF MICROBIOLOGY
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