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Use of 4-arylmethyl curcumin analogues as hsp90 inhibitors

A technology of arylmethyl curcumin and analogues, applied in the field of application as Hsp90 inhibitors in the preparation of anticancer drugs, to achieve the effect of inhibiting proliferation

Active Publication Date: 2017-01-18
FUJIAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The applicant disclosed the preparation method and anti-tumor application of 4-(4-hydroxy-3-methoxybenzyl) curcumin (compound 1) in Chinese patent 200810071179.4, but there is no public report in the literature that the compound is Hsp90 inhibitory agent

Method used

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  • Use of 4-arylmethyl curcumin analogues as hsp90 inhibitors
  • Use of 4-arylmethyl curcumin analogues as hsp90 inhibitors
  • Use of 4-arylmethyl curcumin analogues as hsp90 inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 3-(4-Hydroxy-3-methoxybenzyl)pentane-2,4-dione (intermediate a)

[0038] White solid, melting point 65-68°C. 1 H NMR (CDCl 3 ) δ: 2.08(s, 3H), 2.13(s, 3H), 3.08(d, J =7.2Hz, 1H), 3.58(s, 1H), 3.86 (s, 3H), 4.00(t, 1H), 6.80-6.72 (m,2H), 7.07-6.98(m, 2H). 13 C NMR (CDCl 3 ) δ:23.26, 29.81, 32.02, 33.55, 55.89,70.18, 108.84, 115.60, 115.67, 128.49, 129.77, 131.35, 154.34, 154.70,192.23, 204.41: 2H+ m + ).

Embodiment 2

[0039] Example two 3-(2-chlorobenzyl)pentane-2,4-dione (intermediate b)

[0040] Pale gray oily substance. 1 H NMR (CDCl 3 ) δ:2.03 (s, 3H), 2.16 (s, 3H), 3.24 (d, J =7.6 Hz, 1H), 3.70 (s, 1H), 4.15(t, 1H), 7.22-7.14 (m, 2H), 7.40-7.30 (m, 2H). 13 C NMR (CDCl 3 ) Δ: 23.03, 29.86, 30.54, 31.92, 66.98, 106.84, 127.06, 127.42,127.87, 128.70, 129.70, 131.51, 134.06, 136.93, 192.11,203.18. + )

Embodiment 3

[0041] Example 3 3-(2-fluorobenzyl)pentane-2,4-dione (intermediate c)

[0042] Pale gray oily substance. 1 H NMR (CDCl 3 ) δ:2.07 (s, 3H), 2.16 (s, 3H), 3.17 (d, J =7.6 Hz, 1H), 3.65 (s, 1H), 4.15(t, 1H), 7.15-7.00 (m, 2H), 7.20-7.15 (m, 2H). 13 C NMR (CDCl 3 ) Δ: 23.12, 25.78, 27.74, 29.63, 67.94, 106.76, 115.10, 115.32,115.54, 124.29, 125.02, 126.56, 127.98, 131.29, 159.79, 162.23,192.03, 203.25. MS M / Z: 231.1.1 Na + )

[0043] 2) Synthetic general method of compound 1-9

[0044] Intermediate a, b or c (10mmol) reacted with 0.49g (7mmol) of diboron trioxide and 20ml of ethyl acetate in a 100ml single-necked flask at 40°C for 0.5h with stirring. Add vanillin or 3,4,5-benzaldehyde or 3-pyridinecarbaldehyde (20mmol), tri-n-butyl borate 11ml (40.5mmol), stir and react at room temperature for 0.5 hours, add dropwise 0.2ml (2mmol) of n-butylamine, The addition was completed within 0.5 h, and the reaction was stirred overnight at room temperature. Add 15ml of 0.5M hydroch...

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Abstract

The invention discloses application of a 4-arylmethyl curcumin analogues serving as an Hsp90 inhibitor. The 4-arylmethyl curcumin analog in serving as Hsp90 inhibitor has a structural formula as shown in the specification, wherein Ar is aromatic ring or aromatic heterocycte; at least one of R1, R2 and R3 is non-hydrogen substituent group. According to the application of the 4-arylmethyl curcumin analogue serving as an Hsp90 inhibitor, the 4-arylmethyl curcumin analogue can be applied to preparation of medicaments for treating breast cancer.

Description

technical field [0001] The invention relates to a class of compound 4-arylmethyl curcumin analogs, in particular to an application as an Hsp90 inhibitor in the preparation of anticancer drugs. Background technique [0002] Heat shock protein 90 (Hsp90) is an ATP-dependent molecular chaperone that can stabilize many client proteins, including many proteins necessary for tumor growth and proliferation, such as Her2, BCR-ABL and IKK. Therefore, Hsp90 has become an important anti-tumor target. Hsp90 inhibitors can inhibit the function of client proteins and co-chaperones to inhibit multiple cancer-related targets (1, L. Neckers, P. Workman, Clin Cancer Res .2012, 18, 64-76). The first generation of natural Hsp90 inhibitors are Geldanamycin (GA), Radicicol (RD) and their derivatives. The second-generation synthetic Hsp90 inhibitors mainly use purine and resorcinol as the backbone, and 17 of them have entered clinical research (2, S. Soga, S. Akinaga, Y.Shiotsu, Current Pharm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/255C07C45/74C07D213/50A61K31/12A61K31/4406A61P35/00
CPCC07C49/255C07D213/50
Inventor 刘洋许建华叶敏吴丽贤吴群丹
Owner FUJIAN MEDICAL UNIV
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