Borneol fatly acid ester derivative and preparation containing said derivative

A technology of fatty acid esters and derivatives, which is applied in the field of medicine and can solve problems such as unseen derivatives

Inactive Publication Date: 2005-08-10
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reported borneol derivatives are borneol glucuronide (HUEBNER CF, LINK KP. Note on the bornyl ester of bornyl d-glucuronide. J Biol Chem. 1950Sep; 186 (1): 393-4.) etc. , but no derivatives indicated in the present invention

Method used

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  • Borneol fatly acid ester derivative and preparation containing said derivative
  • Borneol fatly acid ester derivative and preparation containing said derivative
  • Borneol fatly acid ester derivative and preparation containing said derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: Borneolate laurate (BL)

[0015] Take 5g of borneol and add 50mL of dichloromethane to dissolve it, add lauroyl chloride in an equimolar amount, mix well, add 0.5ml of pyridine, react at 30°C for 5 hours, distill off the dichloromethane, add 10ml of water to the resultant, 30 React at ℃ for 0.5 hours to eliminate unreacted lauroyl chloride, add 100ml of water, mix well, extract with dichloromethane three times in total, 30ml each time, combine dichloromethane, remove residual water with anhydrous sodium sulfate, and decompress The dichloromethane was evaporated to obtain the product.

[0016] IR (KBr pellet) ν / cm -1 : Characteristic peaks 1735.4 (ester, C=O), 1160.3 (C-O), 1112.8 (C-O). 13 C NMR (DMSO-d 6 ), δ: 172 (ester, C=O). ESI-MS m / z: 337.6[M] + . Elemental analysis (%) Found: C 62.17, N 8.82, H 3.22; Calculated: C 62.19, N 8.81, H 3.22. proved to be the target compound.

Embodiment 2

[0017] Embodiment 2: Borneol myristate (BM)

[0018] Take 5 g of borneol and add 50 mL of toluene to dissolve it, add myristoyl chloride in an equimolar amount, mix well, add 0.3 g of lutidine (DMAP), reflux at 60°C for 3 hours, distill off the toluene, and add Water 5ml, react at 60°C for 0.5 hours, eliminate unreacted myristoyl chloride, add 100ml of water, mix well, extract with ethyl acetate, a total of three times, 30ml each time, combine the ethyl acetate extracts, wash with anhydrous sodium sulfate The remaining moisture was removed, and the ethyl acetate was distilled off under reduced pressure to obtain the product.

[0019] IR (KBr pellet) ν / cm -1 : Characteristic peak 1 735.8 (ester, C=O), 1161.1 (C-O), 1113.1 (C-O). 13 C NMR (DMSO-d 6 ), δ: 172 (ester, C=O). ESI-MS m / z: 365.6[M] + . Elemental analysis (%) Found: C 62.17, N 8.82, H 3.22; Calculated: C 62.19, N 8.81, H 3.22. proved to be the target compound.

Embodiment 3

[0020] Embodiment 3: Bornean oleate (BO)

[0021] Take 5 g of borneol and add 50 mL of isopropyl ether to dissolve it, add oleic acid chloride at a molar ratio of 1:1.1, mix well, add 1 ml of triethylamine, reflux at 40°C for 7 hours, distill off the isopropyl ether, and Add 5ml of water, react at 60°C for 0.5 hours, eliminate unreacted oleic acid chloride, add 100ml of water, mix well, extract with dichloromethane three times in total, 30ml each time, combine the dichloromethane extracts, and wash with anhydrous sulfuric acid Sodium was used to remove the residual moisture, and dichloromethane was distilled off under reduced pressure to obtain the product.

[0022] IR (KBr pellet) ν / cm -1 : Characteristic peaks 1735.6 (ester, C=O), 1160.6 (C-O), 1113.4 (C-O). 13 C NMR (DMSO-d 6 ), δ: 172 (ester, C=O). ESI-MS m / z: 419.7[M] + . proved to be the target compound.

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Abstract

A derivative of the borneol ester of fatty acid, which is a target auxiliary of the medicine for treating cerebral diseases, is prepared through esterifying reaction between borneol or isoborneol and the straight-chain or branch-chani C5-C30 fatty acid.

Description

Technical field: [0001] The invention relates to the technical field of medicine, in particular discloses a derivative containing borneol and fatty acid (borneol fatty acid ester derivative) and a preparation containing the derivative. Background technique: [0002] There are two types of borneol: natural borneol and synthetic borneol. Natural borneol is a processed product of dipterocarp resin of the Brainaceae plant. Due to the shortage of resources, artificial synthetic products such as camphor and turpentine are used as raw materials (edited by Jiangsu New Medical College. "Dictionary of Traditional Chinese Medicine" Shanghai People's Publishing House, 1977 Year 951.) The structure of an ice sheet is as follows: [0003] [0004] Borneolum is pungent, bitter, slightly cold. GUIXIN, Spleen, Lung Channel. Have one's ideas straightened out refreshing, clear away heat and relieve pain. For febrile coma, convulsions, apoplexy due to phlegm, qi depression and violent sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/06A61K9/107A61K9/127A61K9/14A61K31/215A61P11/04A61P29/00A61P31/04C07C67/08C07C69/03
Inventor 邓意辉吴红兵王绍宁
Owner SHENYANG PHARMA UNIVERSITY
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