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D-benzothiadiazole-TB(-D) derivative as well as synthesis method and application thereof

A technology of benzothiadiazole and synthesis method, which is applied in the directions of drug combinations, chemical instruments and methods, and medical preparations containing active ingredients, etc. problem, to achieve the effects of excellent solid-state luminescence, excellent luminescence performance, and wide variety of

Active Publication Date: 2021-12-03
XUZHOU NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the maximum λ em Although it has reached 576nm, it has not yet entered the red light region, which limits its application in biological imaging and other fields
Moreover, some compounds have a low half-inhibition rate on normal cells, indicating that they have certain cytotoxicity under light exposure; therefore, reasonable modifications to their structures may further increase the Stokes shift and reduce the toxicity of probes to normal cells. , to obtain a highly efficient and low-toxic PDT photosensitizer with infrared emission

Method used

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  • D-benzothiadiazole-TB(-D) derivative as well as synthesis method and application thereof
  • D-benzothiadiazole-TB(-D) derivative as well as synthesis method and application thereof
  • D-benzothiadiazole-TB(-D) derivative as well as synthesis method and application thereof

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Embodiment

[0055] In this example, through a simple reaction in the synthesized benzothiadiazole- The aminopyrimidine or triphenylamine group was introduced on the base, and two benzothiadiazoles were synthesized- base derivatives, two benzothiadiazoles- The structural formula of the base derivative is shown in Table 1:

[0056] The structural formula of compound I and II of table 1

[0057]

[0058] Two benzothiadiazoles - The synthetic method of base derivative comprises the following steps:

[0059] Compound 1 reacts with 2-aminopyrimidine-5-boronic acid 2 to obtain compound I, and compound 1 reacts with 4-boronic acid triphenylamine 3 to obtain compound II. The specific steps are:

[0060] (1) Take compound 1 (2.0mmol), 2-aminopyrimidine-5-boronic acid 2 (4.8mmol), tetrakis(triphenylphosphine) palladium (0.06g) and potassium carbonate (0.53g) into a 100mL round bottom flask in turn 35mL of anhydrous toluene was added under the protection of argon, and the reaction was car...

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Abstract

The invention discloses a D-benzothiadiazole-TB(-D) derivative as well as a synthesis method and application thereof. The structural formula of the D-benzothiadiazole-TB(-D) derivative is shown as a formula I or II. The D-benzothiadiazole-TB(-D) derivative has large Stokes displacement, shows excellent luminescence property, has excellent solid luminescence and has the potential of becoming an excellent OLED (Organic Light Emitting Diode) material. The D-benzothiadiazole-TB(-D) derivative has a wide pH application range and can be applied to a human physiological environment; the D-benzothiadiazole-TB(-D) derivative has effective and good response to viscosity, and has the possibility of becoming a viscosity response fluorescent probe; the D-benzothiadiazole-TB(-D) derivative has recognition capability on Fe<3+> and is expected to become an excellent Fe<3+> fluorescent probe; and the D-benzothiadiazole-TB(-D) derivative has a good PDT effect, can perform dyeing imaging on A549 cells, and expands the variety of photosensitizers.

Description

technical field [0001] The invention belongs to the fields of organic synthesis, analytical chemistry and biological imaging, and specifically relates to a class of D-benzothiadiazole- Synthesis of base(-D) derivatives and their applications in metal ion recognition, photodynamic therapy and bioimaging. Background technique [0002] Photodynamic therapy (Photodynamic Therapy, PDT) is a new method of treating tumors and other diseases with photosensitizing drugs and laser activation. Due to its advantages of low side effects, minimal invasiveness, no obvious drug resistance, high tumor destruction selectivity, and easy combination with other therapies, it has become an important emerging means of clinical tumor precision treatment. Photosensitizers are the core of PDT. Traditional PDT photosensitizers have problems such as visible absorption and poor penetration. Therefore, more and more new high-efficiency photosensitizers have been developed. but based on Photosensitiz...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/08C09K11/06G01N21/64G01N11/00A61K41/00A61P35/00
CPCC07D487/08C09K11/06G01N21/6428G01N21/6486G01N11/00A61K41/0057A61P35/00C09K2211/1044C09K2211/1051C09K2211/1014
Inventor 吴翚池骁炜周杭苑睿张鹏宛瑜
Owner XUZHOU NORMAL UNIVERSITY
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