Nepetalactone-o-bromobenzoic acid ester as well as preparation process and use of nepetalactone-o-bromobenzoic acid ester

A technology of benzoate and nepetalactone is applied in the directions of medical preparations containing active ingredients, organic active ingredients, organic chemistry, etc., to achieve the effects of simple and cheap preparation method, simple structure and strong physiological activity

Active Publication Date: 2013-02-27
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no report to obtain nepetalactone o-bromobenzoate from nepetalactone through o-bromobenzoate esterification

Method used

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  • Nepetalactone-o-bromobenzoic acid ester as well as preparation process and use of nepetalactone-o-bromobenzoic acid ester
  • Nepetalactone-o-bromobenzoic acid ester as well as preparation process and use of nepetalactone-o-bromobenzoic acid ester
  • Nepetalactone-o-bromobenzoic acid ester as well as preparation process and use of nepetalactone-o-bromobenzoic acid ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Weighing nepetalactone (according to the method disclosed in Chinese patent CN201010217622.1, the commercially available nepeta volatile oil obtained by extracting the flower spikes of the Lamiaceae plant Schizonepeta tenuifolia Briq. by steam distillation is prepared by oxidation And get, purity more than 98%) 18.2mg (0.10mmol), o-bromobenzoic acid 50.2mg (0.25mmol, domestic AR grade), DMAP 12.3mg (0.10mmol, domestic AR grade), it is placed in 50mL round bottom flask Add 4mL of dichloromethane (domestic AR grade), stir to dissolve completely, add DCC 51.6mg (0.25mmol, domestic AR grade), react at room temperature (20-25°C), and check the end point of the reaction by TLC. After the reaction, methanol (domestic AR grade) was added dropwise to clarify the solution, and about 500 mg of silica gel (produced by Qingdao Ocean Chemical Factory, used for column chromatography) was added in three times, and the solvent was distilled under reduced pressure to dryness. ...

Embodiment 2

[0021] Structural analysis of the nepetalactone o-bromobenzoate prepared in Example 1:

[0022] HR-ESI-MS: m / z 366.0415 [M+H] + (calculated value C 17 h 17 BrO 4 is: 365.2185); [α] 20.3 D , +82.5° (c 1.0, CH 3 OH).

[0023] IR (KBr pellet, cm -1 ): 3028 (ν Φ-H ); 2931, 2848 (saturated cyclic hydrocarbon ν CH ); 1754 (lactone carbonyl v C＝O ); 1697 (carbonyl v C＝O ); 1627, 1572, 1503, 1447 (conjugated benzene ring ν C＝C ); 864,792,689 (phenyl ring meta-substituted γ Φ-H ).

[0024] UV (CH 3 OH)λ max : 277.6nm, suggesting that the compound has conjugated absorption characteristics. See attached figure 1

[0025] h 1 -NMR (300MHz, CDCl 3 , ppm): δ1.01 (d, 3H, J=6.6Hz, 6'-CH 3 ), 1.11(dd, 1H, J=4.2, 13.2Hz, 5a-H), 1.26(m, 1H, 4a-H), 1.90(s, 3H, 3'-H), 1.99-2.10(m, 2H , 5b-H, 6-H), 2.37(m, 1H, 4b-H), 2.79-2.86(m, 2H, 7-H), 7.32-7.39(m, 2H, Ar-H), 7.65(dd , 1H, J=0.9, 4.5Hz, Ar-H), 7.75 (dd, 1H, J=1.2, 4.5Hz, Ar-H).

[0026] 13 C NMR (75MHz, CDCl 3 , ppm): ...

Embodiment 3

[0028]Example 3: Weighing nepetalactone (according to the method disclosed in Chinese patent CN201010217622.1, the commercially available nepeta volatile oil obtained by extracting the flower spikes of the Lamiaceae plant Schizonepeta tenuifolia Briq. by steam distillation is prepared by oxidation And get, purity more than 98%) 18.2mg (0.10mmol), o-bromobenzoic acid 50.2mg (0.25mmol, domestic AR grade), DMAP 12.3mg (0.10mmol, domestic AR grade), it is placed in 50mL round bottom flask Add 4mL of dichloromethane (domestic AR grade), stir to dissolve completely, add EDCI 47.9mg (0.25mmol, domestic AR grade), react at room temperature (20-25°C), and check the end point of the reaction by TLC. After the reaction, methanol (domestic AR grade) was added dropwise to clarify the solution, and about 500 mg of silica gel (produced by Qingdao Ocean Chemical Factory, used for column chromatography) was added in three times, and the solvent was distilled under reduced pressure to dryness. ...

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Abstract

The invention discloses a nepetalactone-o-bromobenzoic acid ester as well as a preparation process and use of nepetalactone-o-bromobenzoic acid ester. The nepetalactone-o-bromobenzoic acid ester is characterized in that the molecular formula is C17H17BrO4 and the melting point is184-186 DEG C; and the specific rotation of the nepetalactone-o-bromobenzoic acid ester is as shown in the specification. The invention also discloses a method for extracting the nepetalactone-o-bromobenzoic acid ester, and application of the nepetalactone-o-bromobenzoic acid ester in preparation of an anti-herpes virus medicament.

Description

technical field [0001] The invention relates to a nepetalactone o-bromobenzoate, a preparation process and application thereof, and belongs to the technical field of pharmaceutical preparations. Background technique [0002] Nepetalactone (C 10 h 14 o 3 ) is a monoterpene lactone extracted from the Chinese herbal medicine Schizonepetae, which is colorless crystals (ethyl acetate), mp: 188~189°C. TLC is red (10% ethanol sulfate), molecular formula is C 10 h 14 o 3 , whose structure is [0003] [0004] Chinese patent CN01108186.4 discloses the structural map of nepetalactone and its use, which can be used to prepare anti-cold drugs, anti-inflammatory drugs, antibacterial drugs, analgesics, etc. Chinese patent CN201010217622.1 discloses the structure of nepetalactone An improved preparation process simplifies the preparation operation of nepetalactone, improves the yield and reduces the production cost. Infection with herpes virus can cause a variety of human diseas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83A61K31/365A61P31/22
Inventor 丁安伟单鸣秋张丽李念光曹雨诞包贝华
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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