Preparation method of E-3,4-dihydroxyphenylvinyl sulfoxide and application of E-3,4-dihydroxyphenylvinyl sulfoxide as nerve protection drug

A technology of dihydroxyphenyl and hydroxyl protecting groups is applied in the preparation of E-3,4-dihydroxystyryl sulfoxide compounds and its application field as a neuroprotective drug, and can solve the problem that the blood-brain barrier is not easily penetrated. , fast metabolism, etc.

Active Publication Date: 2014-07-23
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the shortcomings of caffeic acid phenethyl ester that is not easy to pass through the blood-brain barrier and has a fast metabolism in the body, we modified its structure to make the new compound easier to pass through the blood-brain barrier and have stronger stability, thereby improving neuroprotective activity

Method used

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  • Preparation method of E-3,4-dihydroxyphenylvinyl sulfoxide and application of E-3,4-dihydroxyphenylvinyl sulfoxide as nerve protection drug
  • Preparation method of E-3,4-dihydroxyphenylvinyl sulfoxide and application of E-3,4-dihydroxyphenylvinyl sulfoxide as nerve protection drug
  • Preparation method of E-3,4-dihydroxyphenylvinyl sulfoxide and application of E-3,4-dihydroxyphenylvinyl sulfoxide as nerve protection drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of 2-(4-chloro)benzylthioacetic acid (1b)

[0033] Using the synthesis method of compound 1a above, 4-chlorobenzyl bromide was used as a reactant to obtain white solid 1b with a yield of 85.5%, m.p.51-52°C. 1 H NMR (400MHz, DMSO-d 6 )δ=12.62(s, 1H, COOH), 7.32-7.50(m, 4H, ArH), 3.82(s, 2H, SCH 2 COOH), 3.14(s, 2H, ArCH 2 S)

[0034] Preparation of 2-(4-tert-butyl)benzylthioacetic acid (1c)

[0035] Using the synthesis method of compound 1a above, 4-tert-butylbenzyl bromide was used as a reactant to obtain white solid 1c with a yield of 73.9%, m.p.75-76°C. 1 H NMR (400MHz, DMSO-d 6 )δ=12.58(s, 1H, COOH), 7.22-7.36(m, 4H, ArH), 3.77(s, 2H, SCH 2 COOH), 3.12(s, 2H, ArCH 2 S), 1.27(s, 9H, C(CH 3 ) 3 ).

[0036] Preparation of 2-(4-trifluoromethyl)benzylthioacetic acid (1d)

[0037] Using the synthesis method of compound 1a above, using 4-trifluoromethylbenzyl bromide as a reactant, a white solid 1d was obtained with a yield of 88.0%, m.p.64-65°C. 1 H...

Embodiment 2

[0049] Preparation of 2-(4-chloro)benzylsulfinylacetic acid (2b)

[0050] Using the synthesis method of compound 2a above, 2-(4-chloro)benzylthioacetic acid was used as a reactant to obtain white solid 2b with a yield of 82.0%, m.p.146-147°C. 1 H NMR (400MHz, DMSO-d 6 )δ=13.14(s, 1H, COOH), 7.31-7.44(m, 4H, ArH), 4.22(d, J=12.4Hz, 1H, SCH 2 COOH), 4.05 (d, J=12.4Hz, 1H, SCH 2 COOH), 3.83 (d, J=14.8Hz, 1H, ArCH 2 SO), 3.50 (d, J=14.8Hz, 1H, ArCH 2 SO)

[0051] Preparation of 2-(4-tert-butyl)benzylsulfinylacetic acid (2c)

[0052]Using the synthesis method of compound 2a above, 2-(4-tert-butyl)benzylthioacetic acid was used as the reactant to obtain white solid 2c with a yield of 73.8%, m.p.145-146°C. 1 H NMR (400MHz, DMSO-d 6 )δ=13.14(s, 1H, COOH), 7.24-7.42(m, 4H, ArH), 4.21(d, J=12.8Hz, 1H, SCH 2 COOH), 4.02 (d, J=12.8Hz, 1H, SCH 2 COOH), 3.86 (d, J=14.4Hz, 1H, ArCH 2 SO), 3.56 (d, J=14.4Hz, 1H, ArCH 2 SO), 1.29(s, 9H, C(CH 3 ) 3 )

[0053] Preparation of 2-(4-t...

Embodiment 3

[0067] Using the synthesis method of compound 2a above, 2-(4-chloro)benzylthioacetic acid was used as a reactant to obtain white solid 2b with a yield of 70.0%.

[0068] Example 4:

[0069] Preparation of 2-benzylsulfinylacetic acid (2a)

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Abstract

The invention relates to an application of E-3,4-dihydroxyphenylvinyl sulfoxide represented by the formula I in preparation of nerve protection drugs for treating neurodegenerative diseases, wherein the definitions of each group in the formula I are listed in the description. The invention also relates to a preparation method of E-3,4-dihydroxyphenylvinyl sulfoxide.

Description

technical field [0001] This patent relates to the use of E-3,4-dihydroxystyryl sulfoxide compounds in the preparation of neuroprotective drugs for neurodegenerative diseases, and also relates to the preparation methods of such compounds. Background technique [0002] Neurodegenerative diseases are a class of chronic, progressive neurological diseases. Such diseases mainly include Alzheimer's disease, Parkinson's disease, amyotrophic lateral sclerosis, Huntington's disease, multiple sclerosis, cerebellar atrophy, different types of spinocerebellar ataxia, spinal muscular atrophy , Primary lateral sclerosis, etc. In recent years, the number of neurodegenerative diseases has been increasing. For example, the prevalence of Alzheimer's disease in my country reaches 2% to 5%, and the annual new incidence reaches 1%. Studies have found that neurodegenerative diseases are caused by many different reasons, including insufficient nutrition provided by neurons or glial cells, hyperac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/18A61K31/10A61K31/222A61P25/28A61P25/16A61P25/00A61P9/10
Inventor 刘俊义宁显玲张志丽郭莹王孝伟田超
Owner PEKING UNIV
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