Crosslinking monomer containing bile acid and preparation process and use thereof

A technology for cross-linking monomers and bile acids, which is applied in the directions of organic chemistry methods, chemical instruments and methods, prostheses, etc., to achieve the effects of high yield, small polymerization shrinkage rate and simple method.

Inactive Publication Date: 2006-05-17
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But Boos et al. mentioned in the patent (WO 99 / 65528) that the method of using methacrylic anhydride or methacryloyl chloride was unsuccessful.

Method used

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  • Crosslinking monomer containing bile acid and preparation process and use thereof
  • Crosslinking monomer containing bile acid and preparation process and use thereof
  • Crosslinking monomer containing bile acid and preparation process and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Dissolve 25g of cholic acid methyl cholic acid in 125mL of methanol, add 0.5ml of concentrated hydrochloric acid, reflux for 20min., cool to 0°C, crystals are precipitated, and the product is obtained by suction filtration. Yield 93%. (Reference Steroids 61 (1996) 664).

Embodiment 2

[0023] Add 10.0 g of cholic acid into a 250 mL three-necked bottle of cholic acid (2′-hydroxyethyl), stir 80 mL of ethylene glycol and raise the temperature to 58° C., then add 0.5 mL of concentrated hydrochloric acid dropwise. Reaction 10h. Add water to precipitate out. Suction filtration, washing with sodium carbonate aqueous solution, water washing pH to 7.0, vacuum drying, to obtain 10.1 g, yield 91%. 1 H-NMR (400MHz, CDCl 3 ) (part): δ / ppm=0.69(s, 3H, 18-H 3 ), 0.89(s, 3H, 19-H 3 ), 1.00 (d, 3H, 21-H 3 ), 3.43(m, 1H, 3α-H), 3.82(m, 3H, 7α-H, COOCH 2 CH 2 OH), 3.97(s, 12α-H), 4.21(t, 2H, COOCH 2 CH 2 OH). Elemental Analysis C 26 H 44 O 6 (FW: 452.63), Calculated: C% 68.99, H% 9.80; Found: C% 68.84, H% 9.87

Embodiment 3

[0024] Example 3 Synthesis of 3α, 12α-dimethylacryloyl cholate

[0025] Dissolve 1.00 g of methyl cholate in a sufficient amount of THF in a 100 mL three-neck flask. While stirring in an ice-water bath, 1.48 g of methacryloyl chloride and 2.39 g of triethylamine in THF were added dropwise. The ice-water bath was removed, and the reaction was carried out at 20° C. for 12 hours. TLC detected that the reaction was complete. Triethylamine hydrochloride was filtered off and THF was evaporated. It was purified by silica gel column chromatography, and the eluent was petroleum ether / ethyl acetate (20 / 7) to obtain 0.61 g of the product with a yield of 46%. 1 H-NMR (400MHz, CDCl 3 ) (part): δ / ppm=0.77(s, 3H, 18-H 3 ), 0.83(d, 3H, 21-H 3 ), 0.91(s, 3H, 19-H 3 ), 1.91(s, 3H, C(CH 3 )=CH 2 ), 1.99(s, 3H, C(CH 3 )=CH 2 ,), 3.65(s, 3H, COOCH 3 ), 3.89(s, 7α-H), 4.60(m, 1H, 3α-H), 5.17(s, 1H, 12α-H), 5.50(s, 1HC(CH 3 )=CH), 5.57(s, 1H C(CH 3 )=CH), 6.04(s, 1H, C(CH 3 )=CH), 6.14...

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Abstract

The invention relates to a bile acid-containing cross-linking monomer and a preparation method thereof. The bile acid-containing cross-linking monomer is a compound of formula (I), wherein, R1=H or CH3; R2=H, OH or OOCC (R1)=CH2; R3=H, OH or OCOC (R1)=CH2; R4 =CH3 or (CH2CH2)nOOCC(R1)=CH2, n=1-3. Vinyl-containing acid chlorides react with bile acid derivatives in the presence of organic tertiary amines to give crosslinking monomers containing two, three and four polymerizable groups. This type of cross-linking monomer has a small polymerization shrinkage, and can be used to replace the organic matrix of dental filling composite materials and prepare the matrix of other hard tissue (bone, joint, tooth, etc.) repair materials. ∴

Description

technical field [0001] The invention relates to a bile acid-containing cross-linking monomer and a preparation method thereof. The present invention can be used for the organic matrix of dental filling composite materials, and can be applied to the matrix of other hard tissue (bone, joint and tooth, etc.) repair materials; its polymer is used for cholesterol, lipids, fatty acids and their salts, bile acids Adsorption of its salts; used as a chiral cross-linking agent for the resolution of optical isomers. Background technique [0002] Bile acids are bioactive and biocompatible amphiphilic (hydrophilic and lipophilic) substances present in the human body (Steroids 61 (1996) 664). There are hydroxyl and carboxyl groups attached to the steroid ring of the bile acid molecule, which is easy to be chemically modified. Therefore, a series of monomers with polymerizable functional groups can be prepared by using bile acid as a raw material through chemical modification, and then pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00A61K6/02A61L27/00C07B57/00
Inventor 朱晓夏王旭东胡祥正张栩黄文强李晨曦
Owner NANKAI UNIV
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