A small molecule heterocyclic dimer and use

A dimer and small molecule technology, which is applied in the application field of small molecule heterocyclic dimer and the preparation of antitumor drugs, can solve the problems of chemotherapy effectiveness, drug toxicity and drug resistance, and achieve good therapeutic effect. , the effect of low toxicity

Active Publication Date: 2022-07-08
INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chemotherapy is a systemic treatment and is one of the most effective methods for treating various tumors, but the effectiveness of traditional chemotherapy is also affected by drug toxicity and drug resistance [3]

Method used

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  • A small molecule heterocyclic dimer and use
  • A small molecule heterocyclic dimer and use
  • A small molecule heterocyclic dimer and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0089] Example 2 Synthesis of Decanediamine-Ligustrazine Dimer

[0090] Add 0.530g ligustrazine acid, 0.723g EDCI, 1.33mL triethylamine, 10mL anhydrous dichloromethane to the round-bottomed flask, stir to dissolve, then add 0.250g decanediamine, stir and react at room temperature for 12h, add 20mL dichloromethane , washed successively with water (2×30 mL) and saturated brine (1×30 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The residue was separated by silica gel column chromatography, and the eluent (petroleum ether / acetone=5 / 1-4 / 1) was used to obtain 0.451 g of a white solid with a yield of 66% (see the synthetic route diagram). image 3 , see the characterization map Figure 4 ).

Embodiment 3 12

[0091] Example 3 Synthesis of dodecanediamine-ligustrazine dimer

[0092] Add 0.456g ligustrazine acid, 0.621g EDCI, 1.14mL triethylamine, 10mL anhydrous dichloromethane into the round-bottomed flask, stir to dissolve, then add 0.250g dodecanediamine, stir and react at room temperature for 12h, add 20mL dichloromethane Chloromethane was washed successively with water (2×30 mL) and saturated brine (1×30 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under reduced pressure. The residue was separated by silica gel column chromatography, and the eluent (petroleum ether / acetone=5 / 1-4 / 1) was used to obtain 0.445 g of white solid with a yield of 72% (see the synthetic route diagram). Figure 5 , see the characterization map Image 6 ).

Embodiment 4

[0093] Example 4 Synthesis of decanediamine-cinnamic acid dimer

[0094] 0.400 g of cinnamic acid, 0.211 g of decanediamine, 0.517 g of EDCI, 0.030 g of DMAP, and 10 mL of anhydrous dichloromethane were sequentially added to the round-bottomed flask, and the reaction was stirred at room temperature for 12 h. A white solid was precipitated, which was filtered with suction, washed with dichloromethane (2×2.5 mL) and water (3×5 mL) in turn, and dried to obtain 0.329 g of a white solid with a yield of 62% (see the synthetic route diagram). Figure 7 , see the characterization map Figure 8 ).

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Abstract

The invention discloses a small-molecule heterocyclic dimer for tumor treatment and its use. The small-molecule heterocyclic dimer has the following structure: Experiments have shown that the small-molecule heterocyclic dimer of the present invention has a broad tumor-inhibiting spectrum and strong anti-tumor activity, and is effective against human cervical cancer cells HeLa and human liver cancer cells Hep G2. , IC of human breast cancer cell MCF-7, human pharyngeal squamous cell carcinoma cell FaDu, human non-small cell lung cancer cell A549 50 reaching the μM level, much higher than the control drug ligustrazine, while the IC on human breast cells MCF 10A 50 higher than that of tumor cells, showing the characteristics of high efficiency and low toxicity. The small molecule heterocyclic dimer of the present invention has potential application value in the development of antitumor drugs.

Description

technical field [0001] The invention belongs to the field of organic synthesis and medicine, in particular to a small-molecule heterocyclic dimer used for tumor treatment and its use, in particular to a small-molecule heterocyclic dimer formed by aliphatic diamine or alicyclic diamine and two small-molecule heterocycles Application of small-molecule heterocyclic dimers in the preparation of antitumor drugs. Background technique [0002] Cancer is a major public health problem worldwide. According to the World Health Organization, malignant tumors are the second leading cause of death in both developing and developed countries. [1,2] . Chemotherapy is a systemic therapy and is one of the most effective ways to treat various tumors, but the effectiveness of traditional chemotherapy is also affected by drug toxicity and drug resistance [3] . It is imminent to find new antitumor drugs targeting the key pathways of cancer cell proliferation. [0003] In the biological world,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/24C07C233/40C07D213/82C07C233/78C07D307/68C07D213/81C07D215/54C07D215/48C07D307/85C07D235/06C07D209/42C07D333/70C07D209/08C07C235/34C07C237/34C07C235/60C07C233/22A61P35/00A61K31/497A61K31/165A61K31/444A61K31/341A61K31/4709A61K31/4184A61K31/343A61K31/381A61K31/404A61K31/197
CPCC07D241/24C07C233/40C07D213/82C07C233/78C07D307/68C07D213/81C07D215/54C07D215/48C07D307/85C07D235/06C07D209/42C07D333/70C07D209/08C07C235/34C07C237/34C07C235/60C07C233/22A61P35/00
Inventor 刘天军王佳雯李国梁洪阁王文智
Owner INST OF BIOMEDICAL ENG CHINESE ACAD OF MEDICAL SCI
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