1, 1 '-biphenyl-2, 6-diphenol compound and application thereof

A technology of compound and diphenol, applied in the field of medicinal chemistry, can solve the problems of obvious toxic and side effects, multi-drug resistance, poor selectivity, etc., and achieve good biological activity

Active Publication Date: 2021-03-16
FUJIAN SANAN SINO SCI PHOTOBIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although traditional chemotherapy drugs have obvious curative effects in clinical practice, their poor selectivity and low targeting lead to obvious side effects and multi-drug resistance, which reduces the quality of life of patients

Method used

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  • 1, 1 '-biphenyl-2, 6-diphenol compound and application thereof
  • 1, 1 '-biphenyl-2, 6-diphenol compound and application thereof
  • 1, 1 '-biphenyl-2, 6-diphenol compound and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0041] The preparation method of compound 3: take 25ml reaction tube, add compound 2 (0.22mmol), compound 1 (0.18mmol), Cs 2 CO 3 (0.36mmol), Pd(PPh 3 ) 4 (0.02mmol), Ar gas was replaced with 1,4-dioxane (2ml) and placed in an oil bath at 80°C for 12h. TLC detected that the reaction was complete. Celite was filtered, the solvent was removed under reduced pressure, and compound 3 was obtained by separation and purification by column chromatography.

[0042] The preparation method of compounds I-1~I-6: Take a 25ml reaction tube, add compound 3 (0.18mmol), DCM 2mL, place in an ice ethanol bath (-15°C), slowly add 0.9ml BBr dropwise 3 (1.0M in DCM), naturally heated up for 12 hours, and TLC detected that the reaction was complete. The system was placed in an ice-water bath and quenched by adding 0.2ml of MeOH. Water and dichloromethane were then added, separated and extracted, dried over anhydrous sodium sulfate, concentrated under reduced pressure, separated and purified by ...

Embodiment 1

[0045] Compound I-1:

[0046] Preparation of compound 1 boronic acid: take a 250ml three-necked flask, add methyl 3-bromo-4-methylbenzoate (2.0 g, 8.77mmol), pinacol diboronic acid ester (4.46g, 17.54mmol), PdCl 2(dppf).DCM (143 mg, 0.175mmol), KOAc (3.44g, 35.08mmol) replace Ar gas first, add 1,4-dioxane (60 ml), and remove oxygen (diaphragm pumping system, replace Ar gas), placed in an oil bath at 80°C for 12 hours, and TLC detected that the reaction was complete. Filter with diatomaceous earth, remove the solvent under reduced pressure, add diethyl ether and water, separate and extract, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, concentrate under reduced pressure, separate and purify by column chromatography (Hexanes / EA=20:1 ) to obtain a relatively pure borate compound, and the excess boron reagent (Hexanes / EA) was removed by recrystallization to obtain a white solid compound 1 borate (1.81g, 75%). Add 20ml of methanol and...

Embodiment 2

[0050] Compound I-2

[0051] Using compound 2 and the corresponding boronic acid 1 as raw materials, I-2 (72mg, 63%) was obtained by referring to the method of compound I-1. 1 H NMR (400MHz, MeOD) δ: 6.84(d, J=1.7Hz, 1H), 6.81(d, J=8.1 Hz, 1H), 6.71(dd, J=8.1, 1.8Hz, 1H), 6.41(s ,2H),1.61–1.53(m,2H),1.32–1.19(m,6H),1.26(s,6H),1.17–1.05(m,2H),0.87(t,J=6.2Hz,3H).

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Abstract

The invention discloses a 1, 1 '-biphenyl-2, 6-diphenol compound and application thereof, and the 1, 1'-biphenyl-2, 6-diphenol compound is a new compound and has good biological activity. Through an in-vitro tumor cell activity experiment method, it is found that the compound has inhibitory activity on tumor cell proliferation and has the potential of developing anti-tumor drugs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a class of 1,1'-biphenyl-2,6-diphenol compounds with broad-spectrum antitumor activity and applications thereof. Background technique [0002] Cancer, also known as malignant tumor, is a malignant and common disease that seriously threatens human health. It has become the "second killer" that threatens human health after cardiovascular disease. In 2019, the data released by the National Cancer Center showed that the death of malignant tumors accounted for 23.91% of all the deaths of residents, and the mortality rate has continued to rise in the past ten years. [0003] Despite important advances in the development of antineoplastic drugs, the current standard of care remains surgical resection, chemotherapy, and radiotherapy. Although traditional chemotherapeutic drugs have obvious curative effects in clinical practice, their poor selectivity and low targeting lead...

Claims

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Application Information

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IPC IPC(8): C07C69/94C07C39/15C07C215/74C07C205/20C07C65/105C07C243/38C07C235/42C07D207/16C07D233/64C07D317/54C07C271/16C07C233/29C07C237/22C07D213/82C07C219/34C07C233/60A61K31/235A61K31/05A61K31/136A61K31/06A61K31/192A61K31/175A61K31/166A61K31/401A61K31/216A61K31/4172A61K31/36A61K31/27A61K31/167A61K31/455A61K31/16A61K31/137A61P35/00
CPCC07C69/94C07C39/15C07C215/74C07C205/20C07C65/105C07C243/38C07C235/42C07D207/16C07D233/64C07D317/54C07C271/16C07C233/29C07C237/22C07D213/82C07C219/34C07C233/60A61P35/00C07C2603/74Y02P20/55
Inventor 不公告发明人
Owner FUJIAN SANAN SINO SCI PHOTOBIOTECH CO LTD
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