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Novel diamine-containing farnesyl thiosalicylic acid derivative and preparation method and medicinal application thereof

A kind of technology of derivatives and diamines, applied in the application field of preparing antitumor drugs and neuroprotective drugs

Active Publication Date: 2012-10-03
福建金化科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Therefore, according to the latest research progress in life science and information science, we use advanced concepts and methods of new drug design to modify and transform the structure of FTA, and introduce other pharmacophore groups, in order to obtain better anti-tumor activity or brain injury neuroprotection than FTA. Strong compound, the present invention discloses a class of new-type diamine FTA derivatives with pharmaceutical value and pharmaceutically acceptable salts thereof, there is no report on this type of compound

Method used

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  • Novel diamine-containing farnesyl thiosalicylic acid derivative and preparation method and medicinal application thereof
  • Novel diamine-containing farnesyl thiosalicylic acid derivative and preparation method and medicinal application thereof
  • Novel diamine-containing farnesyl thiosalicylic acid derivative and preparation method and medicinal application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0138] The preparation of embodiment 1 farnesyl thiosalicylic acid chloride

[0139] Dissolve 0.54 g (1.50 mmol) FTA in 10 mL anhydrous CH 2 Cl 2 0.60 mL (8.27 mmol) of thionyl chloride was added thereto, stirred at 55° C. for 1 hour, and concentrated to obtain farnesylthiosalicylic acid chloride as a yellow oil.

Embodiment 2

[0140] The preparation of embodiment 2N-(2-aminoethyl) farnesyl thiosalicylic acid amide (I1)

[0141] Dissolve 0.30 g (5 mmol) of 1,2-ethylenediamine and 0.20 mL (1.50 mmol) of triethylamine in 5 mL of anhydrous CH 2 Cl 2 0.38 g (1.0 mmol) of farnesyl thiosalicylic acid chloride was slowly added dropwise to 10 mL of anhydrous CH 2 Cl 2 solution, then stirred at room temperature for 1.5 h, concentrated the solvent, evaporated the remaining ethylenediamine, and obtained 0.28 g of yellow oil by column chromatography, with a yield of 70.5%.

[0142] 1 H NMR (CDCl 3 ,300MHz):8.00(m,1H,Ar-H),7.78(m,1H,Ar-H),7.38(m,2H,Ar-H),5.23(m,1H,SCH 2 C H ), 5.08(m, 2H, 2×CH 2 C H =CCH 3 ), 3.56 (d, 2H, J=9.0Hz, SCH 2 ), 2.99-3.05 (m, 4H, 2×NCH 2 ),1.99(m,8H,2×CHC H 2 C H 2 CH),1.53-1.68(m,12H,4×CH 3 );ESI-MS(m / z):401[M+H] + .

Embodiment 3

[0143] Embodiment 3N-(3-aminopropyl) farnesyl thiosalicylic acid amide (I 2 ) preparation

[0144] Referring to Example 2N-(2-aminoethyl) farnesyl thiosalicylic acid amide (I 1 ) preparation method, by reacting 1,2-ethylenediamine and farnesyl thiosalicylic acid chloride in the 1,3-propanediamine substitution method to prepare light yellow oil N-(3-aminopropyl) Farnesylthiosalicylic acid amide (I 2 ), the yield was 70.1%.

[0145] 1 H NMR (CDCl 3 ,300MHz):7.93(m,2H,Ar-H),7.32(m,2H,Ar-H),5.21(m,1H,SCH 2 C H ),5.12(m,2H,2×CH 2 C H =CCH 3 ), 3.51 (d, 2H, J=9.0Hz, SCH 2 ),3.05(m,4H,2×NC H 2 ),1.90-1.99(m,8H,2×CHC H 2 C H 2 CH),1.54-1.69(m,14H,4×CH 3 ,CH 2 C H 2 CH 2 );ESI-MS(m / z):415[M+H] + .

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Abstract

The invention provides a novel diamine-containing farnesyl thiosalicylic acid derivative and pharmaceutically acceptable salt thereof, a preparation method for the derivative and the salt, a medicinal composition containing the derivative, and medicinal application of the derivative, the salt and the composition, particularly application to preparation of anti-tumor medicines and neuroprotection medicines.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a class of novel farnesylthiosalicylic acid derivatives containing diamines and pharmaceutically acceptable salts thereof, their preparation methods, and pharmaceutical compositions containing these derivatives And their medical use, especially in the preparation of antitumor drugs and neuroprotective drugs. Background technique [0002] All-trans farnesyl thiosalicylic acid (abbreviation: FTA, trade name: Salirasib) is the first farnesyl-based Ras protein inhibitor, which can competitively replace F-Ras and F-Ras muteins with half Lectin binds and inhibits Ras-induced downstream signaling pathways (including Raf and P13K signaling pathways) and mTOR (a stimulator of tumorigenesis, which can rely on or independently open P13K signaling pathways), thereby promoting tumor cell apoptosis and inhibiting tumors cell growth. Studies have shown that the IC of FTA on breast cancer cells MCF-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/62C07D295/13C07D211/26C07C319/20A61K31/166A61K31/4453A61K31/40A61K31/495A61K31/5375A61K31/445A61K31/616A61P35/00A61P25/00
Inventor 凌勇杨宇民王新杨肖幼安郭益冰钟梦菊甘东汇丰楠楠
Owner 福建金化科技有限公司
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