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Substituted coumarin-thiazole orange derivatives and their preparation and use

A technology of orange derivatives and coumarin, applied in the field of biochemistry, can solve the problems of unfavorable fluorescence imaging, short fluorescence emission wavelength, etc., and achieve the effects of strong operability, low overall cost and excellent selectivity

Active Publication Date: 2018-11-16
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the fluorescence emission wavelengths of these probes are relatively short, which is not conducive to fluorescence imaging in vivo

Method used

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  • Substituted coumarin-thiazole orange derivatives and their preparation and use
  • Substituted coumarin-thiazole orange derivatives and their preparation and use
  • Substituted coumarin-thiazole orange derivatives and their preparation and use

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preparation example Construction

[0030] The preparation method of the substituted coumarin-thiazole orange derivative comprises the following steps:

[0031] a. Dissolve substituted salicylaldehyde and diethyl malonate in an anhydrous organic solvent, then add piperidine, and reflux for 6 to 8 hours to prepare intermediate 1; the diethyl malonate The dosage is 2.0~2.5 times of substituted salicylaldehyde, and the consumption of said piperidine is 1.2~1.6 times of substituted salicylaldehyde;

[0032] b. Dissolving intermediate 1 in a strong acid and reacting under reflux for 4 to 6 hours to prepare intermediate 2;

[0033] c. Reflux reaction of intermediate 2 and phosphorus oxychloride in anhydrous DMF (N,N-dimethylformamide) for 2.5 to 3.5 hours to prepare intermediate 3; the amount of phosphorus oxychloride 1.6 to 1.8 times that of intermediate 2;

[0034] d, the intermediate 3,2-methylthiazole orange and piperidine were refluxed in absolute ethanol for 12 hours to prepare substituted coumarin-thiazole or...

Embodiment 1

[0042] The synthesis of embodiment 1 intermediate 1:

[0043]

[0044] Dissolve 4-diethylamino salicylaldehyde (10.0g, 56.4mmol), diethyl malonate (18.0g, 112.4mmol), piperidine (2mL, 79.0mmol) in 60mL of absolute ethanol, at 80°C reflow. When the reaction was no longer monitored by TLC (about 6 hours), the solvent was removed under reduced pressure and used directly for the next reaction. 15.6 g of black oily liquid was obtained, and the crude yield was 95.7%.

[0045] 1 HNMR (400MHZ, CDCl 3 )δ8.40(s, 1H), 7.35(d, J=8.8Hz, 1H), 6.66(dd, J=8.9, 2.3Hz, 1H), 6.50(s, 1H), 4.36(q, J=7.15 Hz, 4H), 3.42 (q, J = 7.1 Hz, 4H), 1.36 (t, J = 7.1 Hz, 3H), 1.21 (t, J = 7.1 Hz, 6H).

Embodiment 2

[0046] The synthesis of embodiment 2 intermediate 2:

[0047]

[0048] Intermediate 1 (5.0 g, 17.3 mmol) was dissolved in 150 mL of 18% concentrated hydrochloric acid and refluxed at 100 °C. When the reaction was no longer monitored by TLC (about 5 hours), the reaction was cooled to room temperature, saturated sodium carbonate solution was added, and the pH was adjusted to 4-5 with 45% concentrated sodium hydroxide solution, and a large amount of orange solid was observed to precipitate. After filtration under reduced pressure, a large amount of khaki solid was collected, dried in vacuo to remove water, and used directly for the next reaction. 2.7 g of yellow-green powder was obtained with a yield of 72.0%.

[0049] 1 HNMR (400MHz, CDCl 3 )δ7.54(d, J=9.5Hz, 1H), 7.28(d, J=8.8Hz, 1H), 6.74(bs, 1H), 6.61(s, 1H), 6.08(d, J=9.2Hz, 1H), 3.4 (q, J=7.1 Hz, 4H), 1.19 (t, J=7.1 Hz, 6H).

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Abstract

The invention belongs to the field of biochemistry and particularly relates to a substituted coumarin-thiazole orange derivative, a preparation method therefor and use of the substituted coumarin-thiazole orange derivative. The substituted coumarin-thiazole orange derivative provided by the invention has a structural formula represented by a formula I shown in the description. The invention also provides the preparation method for the substituted coumarin-thiazole orange derivative and use of the substituted coumarin-thiazole orange derivative in fluorescent recognition of G-quadruplex. The substituted coumarin-thiazole orange derivative provided by the invention has the advantages that the toxicity is low, the selectivity is good, the sensitivity is high, raw materials are simply and easily obtained, the whole synthesis route is high in operability, reaction conditions are relatively mild, the overall cost is relatively low, and the like, thereby undoubtedly having better market competitiveness compared with the existing inefficient G-quadruplex fluorescent probes.

Description

technical field [0001] The invention belongs to the field of biochemistry, and specifically relates to a substituted coumarin-thiazole orange derivative, a preparation method and application thereof. Background technique [0002] The G quadruplex is an atypical nucleic acid structure. Four guanine bases can form a G tetramer plane through hydrogen bonding, and the multilayer G tetramer plane can form a G quadruplex. G quadruplexes can be formed from single strands of G-rich DNA or RNA under physiological conditions, and can exist stably in organisms. In 2013, direct evidence for the existence of G-quadruplexes in mammalian cells was presented, and a copolymerization imaging system showed that G-quadruplexes are enriched in the telomeric regions of human chromosomes. [See: G. Biffi, D. Tannahill, J. McCafferty and S. Balasubramanian, Nat. Chem., 2013, 5, 182-186.] Subsequent studies have confirmed that G quadruplexes may be related to cancer by stabilizing G quadruplexes T...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14C09K11/06C12Q1/02
CPCC07D417/14C09K11/06G01N33/505
Inventor 余孝其李坤徐浩然
Owner SICHUAN UNIV
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