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 an

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
Comparison scheme
Effect test

Example Embodiment

[0041] Preparation of Compound 3: Take 25 ml of reaction tube, add compound 2 (0.22 mmol), Compound 1 (0.18 mmol), CS 2 CO 3 (0.36mmol), PD (PPH 3 ) 4 (0.02 mmol), 1,4-dioxane (2 mL) replaced by AR gas was placed at 80 ° C oil bath for 12h, and TLC was detected. Diatomite filtration, removal of the solvent under reduced pressure, and purified the compound 3.

[0042] Preparation of Compounds I-1 to I-6: Take 25 ml of reaction tubes, add compound 3 (0.18 mmol), DCM 2ml, placed in a gladion or bath (-15 ° C), slowly drop 0.9ml BBR 3 (1.0M in DCM), natural heating reaction is 12h, TLC detection is completed. The system was placed in an ice water bath and 0.2 ml of MeOH was quenched. Further, water, dichloromethane, separation extraction, dry dry sodium sulfate, concentrated under reduced pressure, and purify the compounds I-1 to I-6.

Example Embodiment

[0044] Example 1

[0045] Compound I-1:

[0046] Compound 1 boric acid was prepared: 3-bromo-4-methylbenzoate (2.0 g, 8.77 mmol), frequencated borate (4.46 g, 17.54 mmol), PDCl 2(DPPF) .DCM (143 mg, 0.175 mmol), KOAC (3.44 g, 35.08 mmol) first replace AR gas, add 1,4-dioxane (60 mL), oxygen (diaphragm pump system, replacement Ar Qi), placed at an 80 ° C oil bath reaction for 12h, TLC detection reaction. Diatomaceous earth filtration, remove the solvent decompression, ether, water, liquid extraction extraction, combined organic phase, saturated saline water, water absolute sodium sulfate, concentrate reduced pressure, column chromatography isolation purification (Hexanes / EA = 20: 1) The pure boric acid ester compound was obtained, and the excess of the excess boron reactant (Hexanes / EA) was removed in the recombutrial crystal (1.81 g, 75%). The above borate is added to 2.7 ml of methanol, 12 N concentrated sulfuric acid, heating refluxing 12h, TLC detection, concentrated under...

Example Embodiment

[0049] Example 2

[0050] Compound I-2

[0051] I-2 (72 mg, 63%) was obtained with reference to compound I-1 by compound 2, corresponding boric acid 1 as a raw material. 1 H NMR (400MHz, MeOD) δ: 6.84 (D, J = 1.7 Hz, 1H), 6.81 (D, J = 8.1 Hz, 1H), 6.71 (DD, J = 8.1, 1.8 Hz, 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 = 6.2 Hz, 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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