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Oxime compound, preparation process and application thereof

A technology of compound and preparation method, applied in the field of oxime compounds and their preparation and application

Inactive Publication Date: 2010-04-14
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although immunosuppressive drugs have been successfully used in the clinical treatment of organ transplantation and autoimmune diseases, their side effects including hepatotoxicity, nephrotoxicity, malignancy, infection, and cardiovascular toxicity cannot be ignored

Method used

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  • Oxime compound, preparation process and application thereof
  • Oxime compound, preparation process and application thereof
  • Oxime compound, preparation process and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: Preparation of (E)-2-(4-bromophenyl)-1-(3,4-dihydroxyphenyl)ethanone oxime (compound 1)

[0020]

[0021] Add catechol (10mmol) and p-bromophenylacetic acid (10mmol) into a 100ml single-necked round bottom flask, and then add 10ml of boron trifluoride ether (47.0-47.7%, calculated as BF3, the same below). Stir the reaction, heat to 80-84°C and reflux for about 2 hours, then cool, add sodium acetate (8g) to a water (200ml) solution, stir while adding, then stand still, filter after 24h to obtain a brown solid. Put the obtained product into a 100ml beaker, add absolute ethanol to dissolve completely, then filter after recrystallization to obtain yellow crystalline substance 2-(4-bromophenyl)-1-(3,4-dihydroxy) Phenyl ethyl ketone. Then move it into a 100ml single-necked round bottom flask, add sodium acetate and hydroxylamine hydrochloride of equimolar mass, dissolve in ethanol (10ml). Stir and heat to 60°C, reflux for about 3 hours, then detect the reactio...

Embodiment 2

[0022] Example 2: Preparation of (E)-2-(4-bromophenyl)-1-(2,3,4-hydroxyphenyl)ethanone oxime (compound 2)

[0023]

[0024] The preparation method is the same as in Example 1. Pyrogallol was used instead of catechol to obtain the target compound in brown granular form. Yield 63%. Mp 143-1145°C. 1 HNMR (300MHz, DMSO-d6), 4.14(s, 2H), 6.24(s, 1H), 6.39(d, J=9Hz, 1H), 6.90(d, J=8Hz, 2H), 7.08(d, J =9Hz, 2H), 7.88(d, J=9Hz, 1H), 8.71(s, 1H), 9.45(s, 1H), 10.11(s, 1H), 12.45(s, 1H).ESI-MS: 336.99 ([M+H]+).Anal.Calcd for C14H12BrNO4: C, 49.73; H, 3.58; Br, 23.63; N, 4.14; O, 18.93%; found: C, 49.71; H, 3.56; N, 4.15; O, 18.97%.

Embodiment 3

[0025] Example 3: Preparation of (E)-2-(4-methoxyphenyl)-1-(2,4,6-hydroxyphenyl)ethanone oxime (compound 3)

[0026]

[0027] The preparation method is the same as in Example 1. Pyroglucinol was used instead of catechol, and p-methoxyphenylacetic acid was used instead of p-bromophenylacetic acid to obtain the brown powdery target compound. Yield 60%. Mp 143-144°C. 1 H NMR (300MHz, DMSO-d6), 3.93(s, 2H), 6.37(d, J=9Hz, 1H), 6.92(d, J=8Hz, 2H), 7.15(d, J=8Hz, 2H), 7.34(d, J=9Hz, 1H), 9.15(s, 1H), 10.34(s, 1H), 12.11(s, 2H), 12.98(s, 1H). ESI-MS: 289.10([M+H] +).Anal.Calcd for C15H15NO5: C, 62.28; H, 5.23; N, 4.84; O, 27.65%; found: C, 62.24; H, 5.22; N, 4.85; O, 27.67%.

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Abstract

Oxime compound is characterized in that the oxime compound is represented by the following general formula, wherein R1 is multi-hydroxyphenyl, and R2 is substituted benzyl. Oxime derivatives have obvious inhibition action on activated T cells and have weaker inhibition action on inactivated T cells, and then the oxime compound can be applied in preparation of immunosuppressive drug. Further, the invention discloses a process for preparing the oxime compound.

Description

technical field [0001] The invention relates to an oxime compound, a preparation method thereof and an immunosuppressive drug. Background technique [0002] Immunosuppressants are an important clinical drug used in medical procedures including transplant rejection and the treatment of autoimmune diseases such as systemic lupus erythematosus, rheumatoid arthritis and psoriasis. T lymphocytes play an integral role in transplant rejection, making cyclosporine A (CsA), tacrolimus (FK506) and sirolimus (rapamycin) stand out as immunosuppressant treatments . Although immunosuppressive drugs have been successfully used in the clinical treatment of organ transplantation and autoimmune diseases, their side effects including hepatotoxicity, nephrotoxicity, malignancy, infection, and cardiovascular toxicity cannot be ignored. Therefore, the search for new modulators of immune response, and potential new species of immunosuppressive compounds with high efficiency and low toxicity that...

Claims

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Application Information

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IPC IPC(8): C07C251/48C07C249/08A61K31/15A61P37/06
Inventor 朱海亮骆银李环球
Owner NANJING UNIV
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