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2,2-di-cyano methylene thiazole and application thereof

A biscyanomethylenethiazole and application technology are applied in the field of heterocyclic compounds and 2,2-biscyanomethylenethiazole derivatives, which can solve the problems of low photothermal conversion efficiency and achieve good photothermal conversion. Excellent efficiency, photostability and thermal stability

Active Publication Date: 2019-06-28
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the Chinese patent (CN106008525), a triphenylamine-containing 3,6-bis(2-thienyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-bis was designed and synthesized. Ketone (DPP) derivatives are used as tumor photothermal therapy reagents, but their absorption peak is at 660nm, which belongs to the red light region, and the photothermal conversion efficiency is low

Method used

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  • 2,2-di-cyano methylene thiazole and application thereof
  • 2,2-di-cyano methylene thiazole and application thereof
  • 2,2-di-cyano methylene thiazole and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of 2,2-biscyanomethylenethiazole:

[0020] 2-(4-(4-cyanophenyl)thiazole-2(5H)-methylene)malononitrile (1.25g, 5.00mmol) and 4-(diphenylamino)benzaldehyde (1.37g, 5.00 mmol) and ammonium acetate in acetic acid were magnetically stirred at 120° C. for 48 hours under nitrogen protection. The solvent was then added dropwise to saturated sodium bicarbonate solution. After filtration, the filter residue was purified by column chromatography using a mixture of dichloromethane / methanol (18:1) as dark crude solid 0.75 g (34% yield).

[0021] Compound Characterization:

[0022] 1 H NMR(400MHz,MeOD),δ(ppm):7.58~7.59(d,4H),7.33~7.44(m,8H),7.19~7.23(t,2H),7.03~7.06(d,4H),6.68 ~6.70(d,1H).

[0023] 13 C NMR(100MHz,MeOD),δ(ppm):174.58,170.13,153.14,147.08,140.17,135.45,132.37,130.82,130.56,130.05,129.42,126.86,126.08,124.07,120.49,119.20,116.51,112.52,66.82 .

[0024] IR(v -1 ,KBr):3452,2924,2859,2199,1648,1589,1493,1320,1182,1079,838,756,703.

[0025] The above ...

Embodiment 2

[0026] Embodiment 2 (the ultraviolet absorption of 2,2-dicyano methylene thiazoles)

[0027] Prepare 2,2-biscyanomethylenethiazole DMSO solution with a concentration of 1 mM, take 10 μL of 2,2-biscyanomethylenethiazole DMSO solution, add it to a 10 mL centrifuge tube, and dilute to 10 mL with distilled water to obtain a concentration of 10 μM 2,2-Dicyanomethylenethiazole aqueous solution (containing 1% DMSO).

[0028] Adopt Thermofisher Evolution 300 ultraviolet absorption spectrometer to measure the ultraviolet absorption spectrum of above-mentioned 2,2-dicyano methylene thiazole aqueous solution, its result is as follows figure 1 shown. The ultraviolet absorption spectrum of 2,2-biscyanomethylenethiazole shows a strong absorption peak at 758nm, which belongs to near-infrared absorption.

Embodiment 3

[0029] Embodiment 3 (the photostability of 2,2-biscyano methylene thiazoles)

[0030] Prepare 2,2-biscyanomethylenethiazole DMSO solution with a concentration of 1 mM, take 10 μL of 2,2-biscyanomethylenethiazole DMSO solution, add it to a 10 mL centrifuge tube, and dilute to 10 mL with distilled water to obtain a concentration of 10 μM 2,2-Dicyanomethylenethiazole aqueous solution (containing 1% DMSO).

[0031] Adopt 808nm laser irradiation 2,2-dicyano methylene thiazole aqueous solution 10 minutes, adopt ThermofisherEvolution 300 ultraviolet absorption spectrometer to measure the ultraviolet absorption spectrum of above-mentioned 2,2-dicyano methylene thiazole aqueous solution, its result is as follows figure 2 shown. from figure 2 It can be known that there is little change in the ultraviolet absorption spectrum of 2,2-biscyanomethylenethiazole before and after 808nm laser irradiation, indicating that 2,2-biscyanomethylenethiazole has good photostability.

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Abstract

The invention relates to 2,2-di-cyano methylene thiazole. The chemical structure of the 2,2-di-cyano methylene thiazole is shown in a formula (I). The 2,2-di-cyano methylene thiazole is prepared through a reaction of 2-(4-(4-cyanophenyl)thiazole-2(5H)-methylene)malononitrile and 4-(diphenyl amino)benzaldehyde. The 2,2-di-cyano methylene thiazole has near-infrared absorption performance, high photo-thermal conversion efficiency, and excellent light stability and thermal stability, and can be used as a photo-thermal agent.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to heterocyclic compounds, in particular to 2,2-biscyanomethylenethiazole derivatives. Background technique [0002] With the rapid growth and aging of the global population, the incidence and mortality of cancer are increasing rapidly. However, traditional clinical oncology treatments, including chemotherapy, radiotherapy and surgery, exhibit severe side effects. Photothermal therapy (PTT), as one of the non-invasive therapies for tumors, has attracted much attention due to its low toxicity, high selectivity, low drug resistance, few side effects, and high tumor destruction efficiency. PTT largely depends on photothermal agents, which convert absorbed near-infrared light into heat to ablate tumors. [0003] So far, most photothermal agents available for PTT are inorganic materials, including metallic nanomaterials (e.g., Au, Pd, and Ag nanodots), carbon nanomaterials (e.g., graphene...

Claims

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Application Information

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IPC IPC(8): C07D277/30A61K41/00A61P35/00
CPCY02A50/30
Inventor 刘瑞源陈子康周宇平何庚翰
Owner SOUTHERN MEDICAL UNIVERSITY
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