3-(2-naphthyl) acrylamide derivatives as well as preparation method and application thereof

A technology of acrylamide and its derivatives, which is applied in the field of 3-(2-naphthyl)acrylamide derivatives and their preparation and application, and can solve the problems of preventing the growth of malignant tumors, etc.

Inactive Publication Date: 2012-08-22
NANJING AGRICULTURAL UNIVERSITY
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Problems solved by technology

It can be seen that once the activity of EGFR is inhibited, it...
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Abstract

The invention discloses 3-(2-naphthyl) acrylamide derivatives as well as a preparation method and application thereof. 3-(2-naphthyl) acrylamide-like compounds are characterized by having the following general formula: in the formula, R is an aromatic base, a heterocyclic radical and the like. The compounds as inhibitors of an epidermal growth factor receptor (EGFR) can be applied to targeted therapy of tumor cells. The invention discloses the preparation method of the 3-(2-naphthyl) acrylamide derivatives.

Application Domain

Organic compound preparationCarboxylic acid amides preparation +1

Technology Topic

Targeted therapyGrowth factor receptor +5

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  • 3-(2-naphthyl) acrylamide derivatives as well as preparation method and application thereof
  • 3-(2-naphthyl) acrylamide derivatives as well as preparation method and application thereof
  • 3-(2-naphthyl) acrylamide derivatives as well as preparation method and application thereof

Examples

  • Experimental program(15)

Example Embodiment

[0020] Example 1: Preparation of 3-(2-naphthyl)acrylanilide (Compound 1)
[0021]
[0022] Dissolve the newly prepared 3-(2-naphthyl)acryloyl chloride (1mmol) in anhydrous CH 2 Cl 2 (30mL), add NaHCO 3 (0.5g), stir for 5min, add DMAP (5mg), continue to stir for 5min, add aniline (1mmol) to the system, reflux for 5h at 40-50°C. The reaction solution was washed three times with 5% HCl aqueous solution (50 mL), 5% NaOH aqueous solution (50 mL) and clear water (50 mL) successively. The organic phase was taken out and washed with anhydrous Na 2 SO 4 Dry, remove the solvent under reduced pressure, and perform silica gel column chromatography with a mixed solvent of petroleum ether: ethyl acetate = 5:1 as the eluent. The eluate was distilled under reduced pressure to remove the solvent, and recrystallized in ethyl acetate solution to obtain the target compound as white needle-like crystals. The yield was 75%. Mp:161-163℃.ESI-MS([M+H] + ): 274.1. 1 H-NMR(400 MHz, DMSO-d 6 , Δppm): 6.90 (d, 1H), 7.19 (dd, 1H,), 7.32 (d, 1H), 7.43 (dd, 2H), 7.52 (d, 1H), 7.59-7.62 (m, 4H), 7.75 (d, 1H), 7.83 (s, 1H), 7.90 (m, 2H), 8.90 (brs, 1H).

Example Embodiment

[0023] Example 2: Preparation of 3-(2-naphthyl)acryloyl-4-isopropylaniline (Compound 2)
[0024]
[0025] The preparation method is the same as in Example 1. Substituting 4-isopropylaniline for aniline, the target compound was obtained as light yellow needle crystals. The yield was 68%. Mp: 174-175°C. ESI-MS([M+H] + ): 316.2 1 H-NMR(400 MHz, DMSO-d 6 , Δ ppm): 1.21 (d, 6H), 2.84 (m, 1H), 6.89 (d, 1H), 7.28 (d, 2H), 7.30 (d, 1H), 7.48 (d, 1H), 7.59-7.62 (m, 4H), 7.77 (d, 1H), 7.86 (s, 1H), 8.12 (m, 2H), 9.70 (brs, 1H).

Example Embodiment

[0026] Example 3: Preparation of 3-(2-naphthyl)acryloyl-2-chloroaniline (Compound 3)
[0027]
[0028] The preparation method is the same as in Example 1. Substitute 2-chloroaniline for aniline to obtain the target compound with white needle-like crystals. The yield is 70%. Mp: 152-154°C. ESI-MS([M+H] + ): 308.2 1 H-NMR(400MHz, DMSO-d 6 , Δ ppm): 6.93(d, 1H), 7.17(m, 1H), 7.35(m, 1H), 7.42(d, 1H), 7.44(d, 1H), 7.55(m, 2H), 7.68(d , 1H), 7.73 (s, 1H), 7.85 (d, 1H), 7.99-8.03 (m, 3H), 9.23 (brs, 1H).

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