Unsymmetric bifunctional carborane derivatives, and preparation method and application thereof

A bifunctional, carborane technology, applied in chemical instruments and methods, drug combinations, pharmaceutical formulations, etc., can solve the problems of low concentration and limit applications, and achieve the effect of improving high temperature resistance, thermal stability, and great application value

Inactive Publication Date: 2019-03-01
BEIHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although BPA is non-toxic, its low concentration in tumor tissue limits its application, so it is necessary to develop new boron-containing compounds

Method used

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  • Unsymmetric bifunctional carborane derivatives, and preparation method and application thereof
  • Unsymmetric bifunctional carborane derivatives, and preparation method and application thereof
  • Unsymmetric bifunctional carborane derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] The synthesis of embodiment 1 compound 1

[0055] Add 2.32g (10mmol) of methyl 4-iodobenzoate, 120ml of dewatered triethylamine, and 15ml of dehydrated THF into a three-necked flask equipped with stirring, connect the drying device and oxygen removal device, and turn on the magnetic stirring. Pass high-purity nitrogen for about 1 hour, add tetrakistriphenylphosphine palladium 115mg (0.1mmol), cuprous iodide 38mg (0.2mmol), heat up to 50°C, keep warm for 30min, and take 1.45g (11mmol) of 4-methoxy with a syringe Phenylacetylene was quickly injected, and the reaction was monitored by TLC (solid precipitation occurred). The product was filtered, the mother liquor was spin-dried, the solid obtained twice was dissolved with 50ml of dichloromethane (DCM), the organic phase was washed with 1N hydrochloric acid, dried by adding anhydrous magnesium sulfate for 3h, magnesium sulfate was removed, and the solvent was spin-dried to obtain The white solid was vacuum-dried at 40° C. to...

Embodiment 3

[0061] The synthesis of embodiment 3 compound 2

[0062] Add 4.7g of decaborane aniline complex (15mmol) and 100ml of dehydrated toluene to a three-necked flask equipped with a stirring and condensing reflux device, pass nitrogen gas for 30min, turn on magnetic stirring, and add 2.66g (10mmol) of compound 1 , react at room temperature for 1 h, raise the temperature to 110° C., remove the nitrogen, and monitor the completion of the reaction by TLC. The product was cooled to room temperature, and the filtrate (orange-red) was taken by suction filtration, the organic phase was washed with 1N hydrochloric acid, and then washed with distilled water until PH = 7, and anhydrous magnesium sulfate was added to the organic phase after liquid separation. Toluene gave an orange-red viscous liquid, which was recrystallized from ice ethanol and filtered to obtain a white powder, which was dried in vacuum to obtain compound 2 (1.73 g, yield 46.01%). mp: 103°C.

[0063] FT-IR (KBr, cm -1 )...

Embodiment 5

[0066] The synthesis of embodiment 5 compound 3

[0067] Add 3.76g (10mmol) of compound 2 into a three-necked flask equipped with stirring, add 100ml sodium hydroxide solution (0.5mol / L), 60ml tetrahydrofuran, stir, heat up to 65°C, and monitor the reaction by TLC. After the reaction was finished, the pH was adjusted to <2 with concentrated hydrochloric acid, stirred for 30 min, THF was removed by rotary evaporation, recrystallized with distilled water after suction filtration to obtain a white solid, and compound 3 (3.12 g, yield 86%) was obtained by vacuum drying.

[0068] FT-IR (KBr, cm -1 ): 3061-2833 broad peak (carboxyl stretching vibration absorption peak), 2640 and 2592 (-B-H stretching vibration), 1705 (C=O stretching vibration of ARCOOH dyad), 1418 (bending vibration of carboxyl-OH), 1260 (C=O stretching vibration of ether), 1181 and 1081 (characteristic peaks of boron cage skeleton), 940 (bending vibration of carboxyl-OH), 834 (stretching vibration of para-substitu...

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Abstract

The invention relates to the fields of anti-tumor and polymer materials, in particular to unsymmetric bifunctional carborane derivatives, and a preparation method and application thereof. The carborane derivatives are a series of carborane derivatives containing carboxyl and hydroxyl represented by a formula 1, due to the high boron content of a 'boron cage', the difficult problem that existing boron neutron radiation therapy has low boron content can be solved. According to the unsymmetric bifunctional carborane derivatives, due to the super aromatic structure of the 'boron cage', materials are often endowed with excellent high temperature resistance, in addition, two functional groups of the carboxyl group and the hydroxyl group which have different properties are contained, carborane-contained polyester using the hydroxyl and the carboxyl to conduct end capping is prepared through self-condensation, high temperature resistance adhesives can be further prepared, and thus the urgent needs for the high temperature resistance adhesives in the aerospace field are met; and the carborane derivatives have great application value in the booming fields of boron neutron capture therapy andhigh temperature resistance adhesives (please see the specifications for the formula 1).

Description

technical field [0001] The invention relates to an asymmetric bifunctional carborane derivative, a preparation method and application thereof, and belongs to the fields of polymer materials and antitumor medicine. The invention provides a method of synthesizing asymmetric bifunctional carborane derivatives with 4-iodomethyl benzoate and 4-methoxyphenylacetylene as raw materials and using them as monomers to synthesize hydroxyl groups and polycondensate-capped carbon-containing boron Methods and uses of alkyl polyesters. Background technique [0002] Boron neutron capture therapy (BNCT) was proposed by American scientists and has become the best way to deal with brain tumors, especially malignant gliomas. The principle of BNCT is to irradiate B accumulated at the tumor site with thermal neutrons. 10 , using B 10 The energy released by the capture reaction with thermal neutrons kills tumor cells without harming normal tissue cells, thereby achieving the purpose of treating ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C08G63/698C08G63/78C09J167/04A61K41/00A61P35/00
CPCA61K41/0095A61P35/00C09J167/04C07F5/05C08G63/6982C08G63/78
Inventor 单烽森巫婷陈功杨继萍
Owner BEIHANG UNIV
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