Coumarin-modified BODIPY (boron dipyrromethene) derivative as well as preparation and application thereof

A technology of fluoroboridipyrrole and its derivatives, which is applied in the field of fluoroboridipyrrole derivatives, can solve the problem that it is not suitable for the treatment of huge or metastatic tumors, achieve good anti-cancer effect, easy to obtain raw materials, and is conducive to industrial production Effect

Active Publication Date: 2018-08-24
FUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, with the deepening of the research on PDT treatment of tumors, PDT therapy has also exposed its own shortcomings and limitations: PDT is a local treatment technique, mainly for the eradication of tumor lesions, and is not suitable for the treatment of huge or metastatic tumors

Method used

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  • Coumarin-modified BODIPY (boron dipyrromethene) derivative as well as preparation and application thereof

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Embodiment 1

[0026] The preparation of the fluoroboron dipyrrole derivatives modified by coumarin, the specific steps are:

[0027] (1) P-Hydroxybenzaldehyde (2.50 g, 20 mmol), compound (7.00 g, 25 mmol) and K 2 CO 3 (8.28 g, 60 mmol) dissolved in 30 mL DMF, N 2 React at 90°C for 8 hours under protection; after the reaction, remove DMF by rotary evaporation, add water and CH2 Cl 2 (3 × 50 mL) extracted three times, the organic layers were combined and washed with anhydrous Na 2 SO 4 After drying and concentrating by rotary evaporation under reduced pressure; then with CH 2 Cl 2 As the eluent, the concentrated solution was separated by silica gel column chromatography to obtain light yellow oily liquid compound 1: (5.80 g, 90%). 1 H NMR (400 MHz, CDCl 3 ): δ 9.98 (s, 1 H, CHO), 7.82 (d, J = 8.4 Hz, 2 H, ArH), 7.02 (d, J = 8.4 Hz, 2 H, ArH), 4.22 (t, J = 4.8Hz, 2H, OCH 2 ), 3.90 (t, J = 4.8 Hz, 2 H, OCH 2 ), 3.67-3.76 (m, 6 H, OCH 2 ), 3.38 (t, J =4.8 Hz, 2 H, CH 2 N...

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Abstract

The invention discloses a coumarin-modified BODIPY (boron dipyrromethene) derivative as well as preparation and an application thereof. Chemotherapy drug coumarin covalent bonds with clear curative effects are linked to a BODIPY photosensitizer for PDT (photon dynamic treatment), so that a PDT and chemotherapy combined anti-tumor drug, namely, the coumarin-modified BODIPY derivative, is obtained.Meanwhile, the coumarin-modified BODIPY derivative is taken as a research object, a human gastric carcinoma cell BGC-823 is taken as a tested cell line, the in-vitro anti-cancer activity research is carried out, an efficient anti-cancer prodrug is screened out, and a foundation is laid for PDT and chemotherapy combination of the coumarin-modified BODIPY derivative. The synthesis method of the compound is simpler, raw materials are easy to obtain, the cost is low, few side reactions exist, the yield is higher, purification is easy, and industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of anticancer drug design and synthesis, and in particular relates to a coumarin-modified fluoroborate dipyrrole derivative and its preparation and application. Background technique [0002] Cancer is a disease caused by the malfunction of the mechanisms controlling cell growth and proliferation. The basic unit of cancer lesions is cancer cells. In addition to growing uncontrollably, cancer cells can also locally invade surrounding normal tissues and even transfer to other parts of the body through the internal circulatory system or lymphatic system. As a medical problem of global concern, curing cancer and reducing the suffering of cancer patients has become the primary task of scientific researchers. Photodynamic therapy (PDT) is a new type of therapy for malignant tumors under development, and it is a new technology for treating tumors after surgery, chemotherapy and radiotherapy. Compared with traditional treatm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02A61P35/00A61N5/06A61K41/00A61K31/37A61K47/55
Inventor 刘见永杨德潮梁远萍王会花
Owner FUZHOU UNIV
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