Halogenated hydroxyl aromatic methane compounds, preparation method and use thereof

A technology for halogenated hydroxyaromatic methanes and compounds, applied in the field of new compounds and their preparation, can solve the problems of low yield, difficult research and high extraction cost

Inactive Publication Date: 2009-12-16
SHANXI MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In order to solve the problems of high extraction cost, low yield and difficulty in carrying out follow-up research on the lead compounds of halogenated h

Method used

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  • Halogenated hydroxyl aromatic methane compounds, preparation method and use thereof
  • Halogenated hydroxyl aromatic methane compounds, preparation method and use thereof
  • Halogenated hydroxyl aromatic methane compounds, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: 2,3-dibromo-4, the preparation of 5-dihydroxydiphenylmethane I

[0068] (1) 3, the preparation of 4-dimethoxybenzophenone IV

[0069] Put 30ml of anhydrous dichloromethane in an eggplant-shaped bottle, add 5ml (0.036mol) of 1,2-dimethoxybenzene and 5.600g (0.040mol) of benzoyl chloride III under ice-bath conditions, and slowly add trichloromethane in batches Aluminum 5.800g (0.042mol), the system turns brownish red, after 10min, remove the ice and stir in the bathroom, TLC monitors that the reaction is complete after 4h, add ice water to terminate the reaction, extract twice with 50ml dichloromethane, collect the oil phase and dry it. Sodium sulfate was dried and left overnight, and the solvent was removed by rotary evaporation to obtain 7.138 g of a white solid with a melting point of 100°C-102°C and a yield of 82%. 1 HNMR (500MHz, CDCl 3 )δ: 3.984 (d, 6H, CH 3 ), 6.922 (d, 1H, Ph), 7.408 (d, 1H, Ph), 7.508 (t, 3H, Ph), 7.602 (t, 1H, Ph), 7.790 (d, 2H,...

Embodiment 2

[0076]Embodiment 2: 2-chloro-3', the preparation of 4'-dihydroxydiphenylmethane I

[0077] (1) Preparation of 2-chloro-3', 4'-dimethoxybenzophenone V

[0078] Put 30ml of anhydrous dichloromethane in an eggplant-shaped bottle, add 1,2-dimethoxybenzene 5ml (36mmol) at 20 degrees Celsius, p-chlorobenzoyl chloride III 5ml (40mmol), slowly add aluminum trichloride 5.800g ( 42mmol), the system turned brownish red, after 10 minutes, stirred at room temperature, TLC monitored the reaction completely after 1h, added ice water to terminate the reaction, extracted twice with 50ml dichloromethane, collected the oil phase, dried with anhydrous sodium sulfate and placed overnight, The solvent was removed by rotary evaporation to obtain 9.832 g of a white solid with a melting point of 137° C. to 139° C. and a yield of 92%. 1 HNMR (500MHz, CDCl 3 )δ: 3.98 (d, 6H, CH 3 ), 6.87 (d, 1H, Ph), 7.24 (d, 1H, Ph), 7.39 (d, 2H, Ph), 7.43-7.51 (m, 2H, Ph), 7.62 (s, 1H, Ph). ESI-MS (m / z): 277.1, 27...

Embodiment 3

[0083] Embodiment 3: 2,6-dibromo-3,3',4,4', the preparation of 5-trihydroxydiphenylmethane I

[0084] (1) 3,3',4,4', the preparation of 5-pentamethoxybenzophenone IV

[0085] Add 5ml (36mmol) of 1,2-dimethoxybenzene and 20ml of polyphosphoric acid into the eggplant-shaped bottle, stir and dissolve, then add 7.632 (36mmol) of 3,4,5-trimethoxybenzoic acid, and react in an oil bath at 150°C , TLC monitored the reaction to be complete after 4 hours. The reaction was quenched with ice water, and 100 ml of distilled water was added to precipitate a gray solid, which was recrystallized from methanol to obtain 6.520 g of a white solid with a melting point of 115° C. to 117° C. and a yield of 88%. 1 HNMR (500MHz, CDCl 3 )δ: 3.908(s, 6H, CH 3 ), 3.977(t, 9H, CH 3 ) 6.935 (d, 1H, Ph), 7.052 (s, 2H, Ph), 7.430 (d, 1H, Ph), 7.487 (s, 1H, Ph). ESI-MS (m / z): 333.2 ([M+H] + ), 355.2 ([M+Na] + ).

[0086] (2) Preparation of 2,6-dibromo-3,3',4,4',5-pentamethoxybenzophenone V

[0087] We...

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Abstract

The invention relates to novel compounds, a preparation method and use thereof, in particular to halogenated hydroxyl aromatic methane compounds, a preparation method and use thereof, which solves the problem that halogenated hydroxyl aromatic methane lead compounds from natural sources are high in extraction cost, low in yield and difficult to develop follow-up study. The compounds have a structural formula, wherein R1' is one or more hydroxyl or hydrogen atoms in any position on an A ring; R2' is one or more hydroxyl or hydrogen atoms in any position on a B ring; and X is one or more halogen or hydrogen atoms in any position on the A ring or the B ring. A synthesis method has the advantages of mild reaction conditions, widely readily available raw materials, simple preparation method, high yield, low cost and the like, and is suitable for industrial production. The synthesized halogenated hydroxyl aromatic methane compounds and non-toxic salts, ester and ether thereof have the activity of resisting bacteria, tumors, oxidation and vascular endothelial cell injury and inhibiting proliferation of vascular smooth muscle cells.

Description

technical field [0001] The present invention relates to a class of novel compounds and their preparation methods and uses, in particular to a halogenated hydroxyaromatic methane compound and their preparation methods and uses. Background technique [0002] In recent years, research on active substances of seaweed has attracted widespread attention. Among them, bromophenol compounds extracted from seaweed have significant antitumor, antibacterial, hypoglycemic, antithrombotic and antioxidative biological activities (CN101177382A, CN1853618A, CN101283997A, CN101283998A), and are highly potential drug lead compounds . However, due to the low yield and high cost of extracting from seaweed, it cannot meet the needs of new drug development and clinical application, and cannot be widely used. Therefore, finding a synthetic method of halogenated hydroxyaromatic compounds that can be industrially produced and rationally optimizing their structures is beneficial to their further res...

Claims

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Application Information

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IPC IPC(8): C07C39/367C07D213/61C07C37/055A61K31/055A61K31/44A61P31/04A61P31/10A61P35/00A61P39/06A61P43/00A61P9/00A61P9/10A01N31/16A01N43/40A01P1/00A23L1/30C09K15/08C09K15/30A23L33/10
Inventor 李青山赵万一冯秀娥
Owner SHANXI MEDICAL UNIV
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