Compound having anti-itching activity

A compound and antioxidant activity technology, applied in the field of pharmaceutical compounds, can solve problems such as large molecular structure, and achieve the effect of moderate molecular weight and stable structure

Inactive Publication Date: 2010-07-28
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its molecular structure is relatively large,

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] synthetic route:

[0039]

[0040]

[0041] Step A: Compound 1 (Ethyl 2-(1H-imidazol-1-yl)acetate)

[0042] Add imidazole (8.17g, 120mmol), TEA (17.34mL, 120mmol), THF (50mL), ethyl chloroacetate (10.56mL, 100mmol) sequentially, reflux and stir for 10h, suction filter after the reaction, and separate the filtrate by column chromatography 12.1 g of yellow liquid was obtained, and the yield was 78.6% (based on ethyl chloroacetate), 1 H NMR (CDCl 3 -d 6 )δ: 7.49(s, 1H), 7.08(s, 1H), 6.94(s, 1H), 4.68(s, 2H), 4.23(q, 2H), 1.25(t, 3H).

[0043] Step B: Compound 2 (2-(1H-imidazol-1-yl)ethanol)

[0044] Add compound 1 (7.71g, 50mmol), methanol (90mL), LiCl (4.24g, 100mmol) in sequence, slowly add NaBH 4 (4.73g, 125mmol), reacted at 50°C for 8h, separated by column chromatography to obtain 4.31g light yellow oil, and the yield was 76.8% (based on compound 1), 1 H NMR (CDCl 3 -d 6 )δ: 7.47 (s, 1H), 7.02 (s, 1H), 6.91 (s, 1H), 4.01 (t, 2H), 3.65 (m, 2H)....

Embodiment 2

[0055] Example 2 ((R)-2-(2-(4-fluorophenyl)acetamido)-3-phenylpropanoic acid-2-(1H-imidazol-1-yl)ethyl ester)

[0056]

[0057] The operation steps are the same as in Example 1, except that in step D, 4-fluorophenylacetic acid is used instead of 4-nitrophenylacetic acid. The final product is a pale yellow oil, 1 H NMR (CDCl 3 -d 6 )δ: 6.84~7.43 (m, 12H), 4.76 (m, 1H), 4.29 (t, 2H), 4.12 (t, 2H), 3.49 (s, 2H), 2.94 (dd, 2H).

Embodiment 3

[0058] Example 3 ((R)-2-(2-(4-methylphenyl)acetamido)-3-phenylpropanoic acid-2-(1H-imidazol-1-yl)ethyl ester)

[0059]

[0060] The operation steps are the same as in Example 1, and in step D, 4-methylphenylacetic acid is used instead of 4-nitrophenylacetic acid. The final product is a pale yellow oil, 1 H NMR (CDCl 3 -d 6 )δ: 6.81~7.35(m, 12H), 4.75(m, 1H), 4.21(t, 2H), 4.08(t, 2H), 3.49(s, 2H), 2.95(dd, 2H), 2.34(s , 3H).

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PUM

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Abstract

The invention discloses a novel compound having an anti-itching activity, which is as shown in general formula (I) and has obvious anti-itching activity. The invention also relates to a method for preparing the compound and intermediate products thereof.

Description

1. Technical field [0001] The present invention relates to a pharmaceutical compound, in particular to a compound with antioxidant activity. 2. Background technology: [0002] Pruritus is an unpleasant feeling that can cause the desire to scratch. It is also a response mechanism for self-protection in the physiological state of the body, just like warmth, heat, and pain. It is generally caused by skin diseases, biliary tract diseases, thyroid diseases, kidney diseases, malignant tumors and AIDS. According to reports, there were 300 million cases of scabies alone in 2006, and chronic itching caused by lung disease, kidney disease, and hereditary dermatitis is a medical problem, especially itching caused by tumors, which is difficult to understand. Tolerance, routine medical treatment is difficult to detect abnormalities, and the existing antipruritic drugs have no significant curative effect, which seriously affects the quality of life of patients. At the same time, the tra...

Claims

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Application Information

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IPC IPC(8): C07D233/60C07D403/12A61P17/04
Inventor 姚日生江来恩徐峻邓胜松刘璐李婷婷
Owner HEFEI UNIV OF TECH
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