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Chiral dihydropyran ring derivative as well as preparation method and application thereof

A technology of dihydropyran rings and derivatives, applied in the direction of drug combinations, pharmaceutical formulations, organic active ingredients, etc., to achieve good inhibitory effect, excellent inhibitory effect, and good anti-tumor effect

Active Publication Date: 2021-06-08
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Studies have shown that in the presence of chiral phosphoric acid metal salts, metal Lewis acids, tetrakis (3,5-bis (trifluoromethyl) phenyl) silver borate and molecular sieves, the combination of α, β-unsaturated carbonyl compounds with Allene reaction can obtain chiral dihydropyran ring compounds with better enantioselectivity, but how to efficiently control enantioselectivity and diastereoselectivity to synthesize dihydropyran with two chiral centers Cyclic compounds still present certain challenges
Moreover, there is no report on chiral dihydropyran ring compounds with antitumor activity

Method used

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  • Chiral dihydropyran ring derivative as well as preparation method and application thereof
  • Chiral dihydropyran ring derivative as well as preparation method and application thereof
  • Chiral dihydropyran ring derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 Preparation of Chiral Dihydropyran Ring Derivatives

[0052] The specific preparation reaction is as follows:

[0053]

[0054] The hydroxy ketone (0.30 mmol) represented by formula 2, the chiral metal rhodium (0.009 mmol, metal catalyst), Molecular sieves (300mg) were dissolved in 3.0mL of organic solvent dichloromethane to configure mixed solution 1, and the diazo compound (0.6mmol) shown in formula 1 was dissolved in 3.0mL of organic solvent dichloromethane to configure solution 2; in- At 60°C, add solution 2 to the aforementioned mixed solution 1 with a syringe pump within 1 hour, and stir vigorously; after the dropwise addition of the mixed solution is completed, stir at -60°C for 5 to 8 hours until the diazo compound is completely consumed; Filtration, column chromatography separation and purification, to obtain the pure product, namely the target product.

[0055] The structures of the prepared compounds 1 to 32 are shown in Table 1, and the speci...

Embodiment 2

[0092] Example 2 Inhibitory activity of chiral dihydropyran ring derivatives on tumor cells

[0093] (1) The tumor cells used in the test are: human osteosarcoma cells (Sjsa-1), human colon cancer cells (HCT116), human non-small cell lung cancer cells (A549), and human osteosarcoma cells (Saos-2).

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Abstract

The invention belongs to the technical field of medicinal chemistry, and particularly relates to a chiral dihydropyran ring derivative and a preparation method and application thereof. The chiral dihydropyran ring derivative has the structure shown in the formula (I), the derivative is novel in structure, has a good anti-tumor effect, has a good inhibition effect on human osteosarcoma cells, human colon cancer cells and human non-small cell lung cancer cells, and especially has an excellent inhibition effect on the human non-small cell lung cancer cells. The inhibition IC50 of the derivative can be as low as 7 [mu]M. The derivative has a great application value in the anti-tumor effect aspect, and is expected to be prepared into anti-tumor drugs or drugs for inhibiting tumor cell proliferation, especially drugs for resisting human osteosarcoma, human colon cancer and human non-small cell lung cancer. Meanwhile, the preparation method disclosed by the invention has the advantages of cheap and easily available raw materials, few reaction steps, simplicity and safety in operation, low cost, few generated wastes, high atom economy, high selectivity and high yield.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a chiral dihydropyran ring derivative and a preparation method and application thereof. Background technique [0002] Cancer, also known as malignant tumor, is a common and frequently-occurring disease that seriously endangers human health. It has high morbidity, high mortality, high recurrence rate and difficult treatment. Entering the 21st century, malignant tumor is still a serious disease that greatly endangers human life and health, and is the second largest killer threatening human health after cardiovascular disease. Therefore, the treatment of cancer is particularly urgent. The current treatments for tumors include drug therapy, surgery, and radiotherapy. Drug therapy has become an important means of clinical tumor treatment today. According to the different modes of action and chemical mechanisms, anticancer drugs can be divided into drugs that...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/30C07D407/04A61K31/351A61P35/00
CPCC07D309/30C07D407/04A61P35/00
Inventor 钱宇许爱民张芷菁郑日梅尹鑫茹史滔达徐新芳胡文浩
Owner SUN YAT SEN UNIV
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