Benzo[c,d]indole rhodanine compound merocyanine and its synthesis method and application

A synthetic reaction and benzo technology, applied in the field of biomedicine, can solve the problems of not many varieties, difficult active targeting, difficult different needs, etc., and achieve the effects of high product yield and simple and clear experimental operation.

Inactive Publication Date: 2020-01-21
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The PDT photosensitizers currently used or tested in clinical practice are subject to the following limitations: First, there are only a few varieties, and it is difficult to meet different clinical needs; second, some photosensitizers have unsatisfactory action spectra and have good red light penetration in tissues. The absorption in the near-infrared region and the near-infrared region is small, which limits the treatment of deep tumor tissues; third, the specific selectivity to tumor tissues is low, and it is difficult to achieve active targeting
At present, the research to overcome the shortcomings of the above-mentioned PDT photosensitizers is mainly focused on the structural modification of porphyrin derivatives and phthalocyanine derivatives, and there are almost no research reports on PDT photosensitizers with new structures. Therefore, the development of long-wavelength PDT with new structures Photosensitizers have important practical significance

Method used

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  • Benzo[c,d]indole rhodanine compound merocyanine and its synthesis method and application
  • Benzo[c,d]indole rhodanine compound merocyanine and its synthesis method and application
  • Benzo[c,d]indole rhodanine compound merocyanine and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis of 3-ethyl-5-(benzo[c,d]indole-2(1H)-ylidene)-2-thio-1,3-thiazolidin-4-one B1

[0034] Add 3.27g (0.01mol) 2-methylthiobenzo[c,d]indole iodide salt, 1.61g (0.01mol) 3-ethyl rhodanine, 0.66g (0.01 mol) NaAc and 30.0mL absolute ethanol, reflux reaction for 2 h, after cooling, a reddish-brown precipitate precipitated, suction filtered, dried, and recrystallized with toluene to obtain a reddish-brown powder product B12.03g, yield 65.1% , and its melting point is 238-239°C.

Embodiment 2

[0035] Example 2: 2-[3-Ethyl-5-(benzo[c,d]indole-2(1H)-ylidene)-4-carbonyl-1,3-thiazolidine-2-ylidenemethyl Synthesis of ]-3-methylbenzothiazole iodide salt RC1

[0036] Add 0.31g (0.001mol) B1, 0.60g (0.003mol) methyl p-toluenesulfonate, 0.30g (0.001mol) 2,3-dimethylbenzothiazole iodide and 15.0 Add a few mL of N,N-dimethylformamide, drop a few drops of triethylamine as a catalyst, react at 130°C for 1 h, the reaction solution turns from reddish brown to purple red, cool down, precipitate out, filter with suction, dry, use Ethanol Soxhlet extracts the product to obtain 0.22 g of purple-red powdery solid RC1 with metallic luster, the yield is 38.5%, and its melting point is 288-290°C.

[0037] RC1: UV-vis (MeOH) λ max : 575.0 nm, ε: 1.22×10 5 L·mol -1 cm -1 . 1 H NMR (DMSO-d 6 , 400 MHz) δ (ppm): 1.33 (t, 3H, J = 8.0 Hz, CH 2 CH3 ), 4.13 (s, 3H, N-CH 3 ), 4.28 (q, 2H, J = 6.4 Hz, CH 2 CH 3 ), 6.88 (s, 1H, =CH-), 7.10 (d, 1H, J =7.2 Hz, ArH), 7.40-7.48 (m, 2H, ...

Embodiment 3

[0038] Example 3: 10-[3-ethyl-5-(benzo[c,d]indole-2(1H)-ylidene)-4-carbonyl-1,3-thiazolidine-2-ylidenemethyl Synthesis of ]-9-methylacridine iodide salt RC2

[0039] In a dry round bottom flask, add 0.31g (0.001mol) B1, 0.60g (0.003mol) methyl p-toluenesulfonate, 0.34g (0.001mol) 9,10-dimethylacridine iodide and 10.0mL Add a few drops of triethylamine as a catalyst and react at 130°C for 2 h. The reaction solution turns from reddish brown to brilliant red. After cooling, a precipitate precipitates out. Suction filtration, drying, and petroleum The impurity was extracted by Soxhlet ether, and then separated by column chromatography (petroleum ether: ethyl acetate = 5:1) to obtain 0.22 g of brownish black powdery solid RC2 with metallic luster, the yield was 36.1%, and its melting point was 152-154 ℃.

[0040] RC2: UV-vis (MeOH) λ max : 668.5 nm, ε: 4.72×10 3 L·mol -1 cm -1 . 1 H NMR (DMSO-d 6 , 400 MHz) δ (ppm): 1.84 (s, 3H, CH 2 CH 3 ), 3.77 (q, 2H, J = 8.0 Hz,CH...

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Abstract

The invention discloses a benzo[c,d]indole rhodanine compound merocyanine and its synthesis method. It is used as a photosensitizer in photodynamic therapy for the first time, its dark toxicity and phototoxicity are studied, and the relationship between phototoxicity and concentration is discussed. The relationship between. The results showed that benzo[c,d]indole rhodanine complex merocyanine RC1, RC2 and RC4 had very low toxicity to SMMC‑7721 cells in the absence of light. However, RC1 and RC2 had obvious phototoxicity to SMMC‑7721 cells under light. The rhodanine complex merocyanine can be used as a potential photosensitizer in the field of PDT.

Description

technical field [0001] The invention relates to a benzo[c,d]indole rhodanine compound merocyanine, a synthesis method thereof and an application as a photosensitizer in photodynamic therapy, belonging to the field of biomedicine. Background technique [0002] With the increasing destruction of the ecological environment, the types and incidence of cancer are increasing day by day. At present, radiotherapy and chemotherapy still cannot meet the needs of cancer treatment. Photodynamic therapy, as an emerging tumor treatment method, has attracted widespread attention. Photosensitizer is a specific drug used in photodynamic therapy of tumors, and is the core substance of PDT, which directly determines the efficacy of PDT and the clinical application and promotion of this therapy. The earliest photosensitizer used in PDT is hematoporphyrin derivative (HpD), which belongs to the first generation of photosensitizer. Disadvantages such as obvious response limit the clinical promot...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14A61K41/00
CPCA61K41/0057C07D417/14
Inventor 张丹丹高登峰关丽闫梦琦王兰英
Owner NORTHWEST UNIV
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