2-phenylnaphthalene derivative and application thereof in preparation of anti-tumor medicaments

An anti-tumor drug, the technology of phenylnaphthalene, which is applied in the field of 2-phenylnaphthalene derivatives and its application in the preparation of anti-tumor drugs, can solve the problems of high cost, complex structure, cumbersome synthesis, etc., and achieve convenient synthesis, The effect of simple structure and low cost

Inactive Publication Date: 2013-07-10
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on the current research status of 2-phenylnaphthalene derivatives, due to its complex structure, there are still problems of cumbersome synthesis, high cost and unclear biological mechanism of action

Method used

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  • 2-phenylnaphthalene derivative and application thereof in preparation of anti-tumor medicaments
  • 2-phenylnaphthalene derivative and application thereof in preparation of anti-tumor medicaments
  • 2-phenylnaphthalene derivative and application thereof in preparation of anti-tumor medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of compound 2-(6-methoxynaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (structural formula 2, wherein R 2 ’=OCH 3 , R 1 ’=R 4 ’ = H)

[0037] Put 2-methoxy-6-naphthol (1 mol) and dipivaloyl diboron (1.2 mol) into dioxane (10ml), add potassium acetate (3 mol), and add Pd- DPPF (2% mol), heated to reflux for 24 hours, extracted with ethyl acetate,

[0038] The extract was purified by silica gel column chromatography, eluting with petroleum ether: acetone = 10:1.

[0039] 1 H NMR (600MHz, CDCl 3 ,δ):8.29(s,1H),7.81(d,J=12.0Hz,1H),7.78(d,J=12.0Hz,1H),7.73(d,J=12.0Hz,1H),7.14(d ,J=12.0Hz,1H),7.12(s,1H),3.93(s,3H),1.39(s,12H); 13 C NMR (125MHz, CDCl 3 ,r.t.):δ158.5,136.41,136.0,131.1,130.3,128.4,125.9,118.7,105.6,83.3,55.3,24.9; MS(ESI):m / z285.2[M+H] + .

[0040] Prepare compound 2-(3,4-dimethoxyphenyl)-6-methoxynaphthalene- (structural formula 4, wherein R 2 ’=R 2 ''=R 3 ''=OCH 3 , R 1 ’=R 4 ’=R 1 ''=R 4 ''=R 5 ''=H)

[0041] Put 3,4-...

Embodiment 2

[0047] Prepare compound 2-methoxy-5-(6-methoxynaphthalen-2-yl)benzaldehyde (structural formula 5, wherein R 2 ’=CHO,R 2 ''=R 3 ''=OCH 3 , R 1 ’=R 4 ’=R 1 ''=R 4 ''=R 5 ''=H)

[0048] 2-Methoxy-5-bromobenzaldehyde (1.5 mol) and 2-(6-methoxynaphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 mol) Put it in dioxane (10ml), add potassium fluoride (3 mol), add Pd-DPPF (2% mol) under nitrogen protection, heat and reflux for 24 hours, extract with ethyl acetate, and use silica gel column chromatography for the extract Purification, petroleum ether: acetone = 10:1 elution.

[0049] 1 H NMR (600MHz, CDCl 3 ,δ):10.55(s,1H),8.19(d,J=6.0Hz,1H),7.96(s,1H),7.91(dd,J=12.0Hz,J=6.0Hz,1H),7.81(d ,J=6.0Hz,1H),7.79(d,J=6.0Hz,1H),7.69(dd,J=12.0Hz,J=6.0Hz,1H),7.18(dd,J=12.0Hz,J=6.0 Hz,1H),7.16(d,J=6.0Hz,1H),7.11(d,J=6.0Hz,1H),4,04(s,3H),3.94(s,3H); 13 C NMR (100MHz, CDCl 3 ,δ):189.9,161.2,157.8,134.6,134.3,133.8,133.7,129.6,129.2,127.4,126.8,125.5,125.1,125.0,119.3,112.2,105....

Embodiment 3

[0054] Preparation of compound 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalene-2-ol (structural formula 2, wherein R 2 ’=OH,R 1 ’=R 4 ’ = H)

[0055] Put 2-hydroxy-6-naphthol (1 mole) and dipivaloyl diboron (1.2 moles) into dioxane (10 ml), add potassium acetate (3 moles), and add Pd-DPPF under nitrogen protection ( 2% mol), heated to reflux for 24 hours, extracted with ethyl acetate, and the extract was purified by silica gel column chromatography, eluting with petroleum ether: acetone = 10:1.

[0056] 1 H NMR (600MHz, Acetone-d 6 ,δ):8.31(s,1H),7.95(d,J=12.0Hz,1H),7.86(d,J=12.0Hz,1H),7.80(d,J=12.0Hz,1H),7.21(d ,J=12.0Hz,1H),7.16(s,1H),1.40(s,12H); 13 C NMR (125MHz, Acetone-d 6,δ):159.2,137.3,136.2,131.7,130.68,128.9,126.2,119.1,106.0,83.7,24.7; MS(ESI):m / z271.2[M+H] + .

[0057] Preparation compound 6-(4-hydroxy-3-(hydroxymethyl)phenyl)naphthalen-2-ol (structural formula 5, wherein R 2 ’=CH 2 OH,R 2 ''=R 3 ''=OH,R 1 ’=R 4 ’=R 1 ''=R 4 ''=R 5 ''=H...

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Abstract

The invention discloses a 2-phenylnaphthalene derivative. The structural formula is as shown in formula (I), wherein R1 is hydrogen, R2 is hydroxy or hydrogen, R3 is hydroxy or hydrogen, R4 is hydrogen, R5 is hydrogen, R6 is hydrogen, R7 is hydroxy or hydrogen, R8 is hydroxy or hydrogen and R9 is hydrogen. The compound is obtained by utilizing suzuki coupling and boron tribromide demethylation. Tests prove that the 2-phenylnaphthalene derivative disclosed by the invention can significantly inhibit proliferation and migration of tumor cells, has development potential in preparation of medicaments for resisting breast cancer, breast ductal cancer, lung cancer, cervical cancer, prostatic cancer, colon cancer and gastric cancer, and has good application prospects.

Description

technical field [0001] The invention relates to a class of phenylnaphthalene derivatives and applications thereof, in particular to a class of 2-phenylnaphthalene derivatives and their application in the preparation of antitumor drugs. Background technique [0002] With the increasing incidence of malignant tumors year by year, finding effective anti-tumor drugs has long been the primary research task of the world's pharmaceutical industry. Most of the anti-tumor drugs on the market are small molecular compounds, and most of them are derived from natural products and their derivatives. Due to the low yield and limited access to natural products, the synthesis of a new generation of anti-tumor drugs has always been a research hotspot of anti-tumor drugs. [0003] Richard E.M. found that 2-phenylnaphthalene compounds can competitively bind to estradiol β receptors, and it has stronger affinity and higher selectivity than the natural product canaryside. The compound also has ...

Claims

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Application Information

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IPC IPC(8): C07C39/14C07C37/055C07C45/61C07C47/57C07C37/18A61K31/05A61K31/11A61P35/04A61P35/00
Inventor 沈月毛沈燕陈旺鲁春华
Owner SHANDONG UNIV
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