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Anti-herpes simplex virus (HSV) cincumol derivative

A technology of herpes simplex virus and curcumitol, applied in the field of medicine, can solve problems such as poor water solubility, achieve the effects of stable quality, good research and development prospects, and simple preparation process

Active Publication Date: 2015-03-25
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to its poor water solubility, it is only easily soluble in small polar organic solvents such as ethanol, acetone, and chloroform, and has not been developed into clinical medicine for a long time.
In view of the limitation of chemically variable sites in its structure, so far there are few reports on its structural modification by organic chemical methods

Method used

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  • Anti-herpes simplex virus (HSV) cincumol derivative
  • Anti-herpes simplex virus (HSV) cincumol derivative
  • Anti-herpes simplex virus (HSV) cincumol derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of compound of the present invention (1)

[0041] Preparation of intermediates:

[0042] Dissolve m-CPBA (17.2g, 1mol) in dichloromethane (100ml), add curcumol (11.8g, 0.05mol) in dichloromethane (100ml) solution at 0°C, keep stirring at 0°C for 2 hours . After the reaction, the reaction liquid was extracted three times with NaOH (2 mol / l) solution, the organic phases were combined, extracted with water until neutral, and dried over anhydrous sodium sulfate. The solution was concentrated and evaporated to dryness, and the crude product was purified by silica gel column chromatography (cyclohexane:ethyl acetate=50:1~10:1) to obtain 11.95 g of white waxy solid 10,14-epoxycurcumol, yield 95% .

[0043]10,14-epoxycurcumol (10.08g, 0.04mol) was dissolved in acetonitrile (600ml), and lithium perchlorate trihydrate (6.4g, 0.04mol) and diethylamine (20ml) were added at room temperature. The resulting mixture was heated to reflux overnight. The...

Embodiment 2

[0047] Embodiment 2: the preparation of compound of the present invention (2)

[0048] Preparation of intermediate: same as the preparation method of intermediate in Example 1.

[0049] Preparation of target compound (2):

[0050] Dissolve (1S,4S,5S,7S,8R)-5,8-epoxy-9,10-en-14-chloroguaiacol (27mg, 0.1mmol) in acetone (4ml) and add Nitrophenol (16.6 mg, 0.12 mmol), anhydrous potassium carbonate (20.7 mg, 0.15 mmol), potassium iodide (5 mg, 0.03 mmol). The resulting mixture was heated to reflux for 3 hours. The reaction solution was concentrated and evaporated to dryness, and the obtained crude product was purified by PTLC (cyclohexane:ethyl acetate=2.5:1, eluted with ethyl acetate) to obtain colorless oily compound (1S,4S,5S,7S,8R)-5,8 - Epoxy-9,10-ene-14-m-nitrophenoxyguaiacol (2) 26.1 mg, yield 70%. The spectral data of the compound is as follows: MS(ESI)m / z:396.0[M+Na] + ; 1 H-NMR (300MHz, CDCl 3 )δ(ppm): 2.08(1H,dd,J=6.4,9.3Hz,H-1), 1.93(1H,m,H-2a), 1.59(1H,m,H-2b),...

Embodiment 3

[0051] Embodiment 3: the preparation of compound (3) of the present invention

[0052] Preparation of intermediate: same as the preparation method of intermediate in Example 1.

[0053] Preparation of target compound (3):

[0054] Dissolve (1S,4S,5S,7S,8R)-5,8-epoxy-9,10-ene-14-chloroguaiacol (27mg, 0.1mmol) in acetone (4ml) and add Nitrophenol (16.6 mg, 0.12 mmol), anhydrous potassium carbonate (20.7 mg, 0.15 mmol), potassium iodide (5 mg, 0.03 mmol). The resulting mixture was heated to reflux for 3 hours. The reaction solution was concentrated and evaporated to dryness, and the obtained crude product was purified by PTLC (cyclohexane:ethyl acetate=2.5:1, eluted with ethyl acetate) to obtain colorless oily compound (1S,4S,5S,7S,8R)-5,8 - Epoxy-9,10-ene-14-p-nitrophenoxyguaiacol (3) 31.7 mg, yield 85%. The spectral data of the compound is as follows: MS(ESI)m / z:396.0[M+Na] + ; 1 H-NMR (300MHz, CDCl 3 )δ(ppm): 2.07(1H,t,J=7.8Hz,H-1), 1.88(1H,m,H-2a), 1.59(1H,m,H-2b), 1.9...

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Abstract

The invention which belongs to the technical field of medicines relates to new compounds with the anti-HSV activity and having a general formula represented by formula (I). R in the formula (I) is defined in the specification. The invention also relates to a use and preparation methods of the compounds, and an application of the compounds in the clinical preparation of clinically acceptable medicines for treating HSV-infected diseases through combining the compounds with pharmaceutically acceptable carriers. The structure of the general formula (I) is shown in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an anti-herpes simplex virus HSV curcumol derivative. technical background [0002] Herpes simplex virus belongs to Herpesviridae and αherpesvirinae. It is the earliest discovered human herpesvirus. It is divided into two serotypes, type 1 (HSV-1) and type 2 (HSV-2). Global distribution. HSV-1 mostly infects the skin and mucous membranes of the mouth, lips, and eyes, as well as the central nervous system, and occasionally occurs in genital infections (Ann Intern Med, 1983, 98 (6): 958-972; J Med Virol, 1977, 1 (3) : 175-181); HSV-2 is mostly associated with neonatal infection and genital infection. Serological surveys show that the level of HSV antibody is directly related to age and socioeconomic status. In most underdeveloped countries, the positive rate of HSV-1 antibody in people over 30 years old is nearly 90%; about 50-60% of the middle-class people in the United States ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08A61K31/35A61P31/22
Inventor 邱峰李天宪王绍杰陈丽霞康宁罗桓
Owner SHENYANG PHARMA UNIVERSITY
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