No-clean aggregation-induced cell membrane targeted dyeing reagent based on purine skeleton, preparation method and application thereof
A technology of aggregation induction and dyeing reagents, applied in the preparation of test samples, styrene-based dyes, chemical instruments and methods, etc., can solve the problems of low accuracy of imaging results, complicated operation process, and inability to connect sensing, etc., to achieve Avoid the interference of background light, the raw materials are economical and easy to obtain, and the overall cost is low
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Example Embodiment
[0066] Example 1:
[0067] The preparation method of the purine skeleton-based aggregation-inducible cell membrane targeted staining reagent of this embodiment includes the following steps:
[0068] (1) Synthesis of the first intermediate: 2,6-dichloro-9-n-propyl-9-hydro-purine
[0069] The synthetic route is as follows:
[0070]
[0071] 2,6-Dichloropurine (1.0 mmol), 1-bromopropane (1.5 mol) and potassium carbonate (3.0 mmol) were mixed and stirred in DMSO (5 mL) for 6 hours, and then 100 mL of water was added. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (30 mL×3). The organic extract was washed with brine and Na 2 SO 4 dry. After the solvent is distilled under reduced pressure, it is purified by 200-300 mesh silica gel column chromatography. It was eluted with petroleum ether / ethyl acetate (3:2) to obtain the first intermediate as a white solid with a yield of 57%. The eluent is ethyl acetate / petroleum ether=2:3 (V / V). A white solid ...
Example Embodiment
[0089] Example 2:
[0090] This embodiment is basically the same as embodiment 1, except that the third intermediate R is changed. 3 The synthetic route is as follows:
[0091]
[0092] After adding the third intermediate (381 mg, 1 mmol) and 1,4-lutidine-1-iodide (235 mg, 1 mmol) to ethanol (10 mL), piperidine (0.05 mL) was dropped into the stirring solution. Then the mixture was stirred at room temperature for about 12 hours. After the completion of the reaction was monitored by thin layer chromatography, the solvent was removed by rotary evaporation, and then the mixture was dissolved in saturated potassium hexafluorophosphate acetone solution (10 mL). After stirring for 2 hours at room temperature, acetone was distilled off under reduced pressure, and then filtered to obtain a crude product. The crude product was purified by neutral alumina column chromatography. It was eluted with methanol / dichloromethane=20 / 1 (V:V) to obtain a yellow solid with a yield of 37%.
[0093] 1 H N...
Example Embodiment
[0095] Example 3:
[0096] This example is basically the same as Example 1, except that the picoline salt in step (4) is replaced with 4-methyl-1-(3-(trimethylammonium)propyl)pyridine-1-ammonium bromide , The synthetic route is as follows:
[0097]
[0098] A dark brown solid was obtained with a yield of 33%. 1 H NMR(400MHz, DMSO-d 6 )δ9.23-9.20(d,1H), 9.09-9.03(m,3H), 8.71-8.69(s,1H), 8.62-8.57(d,2H), 8.37-8.33(d,2H), 8.20- 8.14(d,1H),8.02-7.98(d,2H),7.74-7.67(m,2H),7.47-7.42(t,1H),7.34-7.28(t,1H),6.95-6.93(d,1H) ), 4.65-4.60(t, 2H), 4.40-4.34(t, 2H), 3.11-3.7(s, 9H), 1.99-1.92(m, 2H), 0.89-0.83(t, 3H). 13 C NMR(101MHz, DMSO-d 6 )δ157.08,154.10,153.50,149.06,146.25,145.04,140.83,139.78,137.37,135.68,130.69,129.15,129.00,128.93,124.83,124.58,124.36,123.26,121.57,121.29,116.71,109.99,108.61,62.25 ,52.91,45.50,24.47,23.06,11.51.HRMS(ESI):m / z:Calcd for C 35 H 39 F 6 N 7 P + :702.2903; [M-PF 6 ] + Found: 702.2902.
[0099] The hydrogen spectrum, carbon spectrum and high resolution mas...
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.
© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap