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Oxygen bridge bis-heptylene sulfonamide compound containing suberic acid monoanilide group as well as synthesizing method, application and anti-breast cancer drug composition of oxygen bridge bis-heptylene sulfonamide compound

A technology of suberoyl anilide and bisheptene sulfonamide, applied in the field of medicine, can solve the problems of ERβ without any activation activity and low endogenous value-added activity

Active Publication Date: 2017-08-18
武汉宏兹生物技术有限公司
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0005] Recently, our research group reported a class of OBHS derivatives containing sulfonamide groups (OBHSA, compound B, formula 1), and several compounds showed similar activity to the clinical drug fulvestrant in cell transcription activity, but The endogenous proliferation activity is significantly lower than that of hydroxytamoxifen and the parent compound OBHS, and it is a pure antagonist without any activation activity on ERβ

Method used

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  • Oxygen bridge bis-heptylene sulfonamide compound containing suberic acid monoanilide group as well as synthesizing method, application and anti-breast cancer drug composition of oxygen bridge bis-heptylene sulfonamide compound
  • Oxygen bridge bis-heptylene sulfonamide compound containing suberic acid monoanilide group as well as synthesizing method, application and anti-breast cancer drug composition of oxygen bridge bis-heptylene sulfonamide compound
  • Oxygen bridge bis-heptylene sulfonamide compound containing suberic acid monoanilide group as well as synthesizing method, application and anti-breast cancer drug composition of oxygen bridge bis-heptylene sulfonamide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] Example 1: 5,6-bis(4-hydroxyl)-7-oxobicyclo[2.2.1]-5-heptene-2-sulfonyl-(4-anilinoformylheptanoic acid methyl ester)-amine Preparation of (32a)

[0123]

Embodiment 2

[0124] Weigh 3,4-bis(4-hydroxy-phenyl)furan (200mg, 0.793mmol) and ethylene 4-(4-(7-anicarboylheptanoic acid methyl ester))-sulfonamide (350.7mg, 0.952 mmol) was placed in a two-necked round-bottom bottle of 50mL and then slowly warmed up to 90° C., spin-dried after 3 hours of reaction, and separated and purified by direct column chromatography. The eluent ratio was dichloromethane:methanol=60:1 to obtain 413.6 mg white solid, yield 94%, m.p.108-110°C; 1 H NMR (400MHz, Acetone-d 6 )δ 9.29(s,1H,-CONH-),8.87(s,1H),7.76(s,1H),7.50(d,J=8.4Hz,1H),7.22(t,J=8.0Hz,1H) ,7.16(d,J=8.4Hz,2H),7.10(d,J=8.8Hz,1H),7.02(d,J=8.8Hz,2H),6.78(d,J=8.4Hz,2H),6.74 (d,J=8.4Hz,2H),5.52(s,1H),5.33(d,J=4.0Hz,1H),3.60(s,3H),3.55(m,1H),2.40(t,J= 7.2Hz, 2H), 2.34(m, 1H), 2.28(t, J=7.6Hz, 2H), 1.98(m, 1H), 1.69(t, J=7.2Hz, 2H), 1.57(t, J= 6.4Hz,2H),1.35(m,4H). 13 C NMR (100MHz, Acetone-d 6)δ174.32,172.65, 158.24,158.04,141.95,141.33,139.74,138.27,130.47,129.79,129.37,125.04,124.56, 116.47,116.41,116.03...

Embodiment 3

[0127] Example 3: 5,6-bis(4-hydroxyl)-7-oxobicyclo[2.2.1]-5-heptene-2-N-ethylsulfonyl-(7-anilinoformylheptanoic acid methyl Preparation of ester)-amine (33b)

[0128]

[0129] The preparation method is as in Example 1, the product is light yellow powder, the yield is 95%, m.p.105-108°C; 1 H NMR (400MHz, Acetone-d 6 )δ9.26(s,1H,-CONH-),8.70(s,2H,-OH),7.75(s,1H),7.64(d,J=8.4Hz,1H), 7.25(t,J=8.4 Hz,1H),7.19(d,J=8.0Hz,2H),7.18(d,J=8.0Hz,2H),7.07(d,J=8.0Hz,1H),6.82(d,J=8.4Hz, 2H), 6.80(d, J=8.0Hz, 2H), 5.49(s, 1H), 5.33(d, J=3.6Hz, 1H), 3.82(m, 2H), 3.60(s, 3H), 3.54( m,1H),2.38(t,J=7.6Hz,2H),2.28(t,J=7.2Hz,2H),2.19(m,1H),2.06(m,1H),1.69(t,J=6.4 Hz,2H),1.58(t,J=7.2Hz,2H),1.36(m,4H),1.04(t,J=7.2Hz,3H). 13 C NMR (100MHz, Acetone-d 6 )δ174.28,172.48,158.23,141.95,141.01,140.67, 138.40,130.42,129.99,129.81,129.56,125.26,124.63,124.43,121.00,119.20,116.53,116.39, 85.27,83.70,62.75,51.59,47.07,37.65,34.30 ,31.30,29.61,29.53,26.01,25.52,14.95; HRMS(ESI)calcd for C 35 h 39 N 2...

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Abstract

The invention belongs to technical field of medicines and specifically relates to an oxygen bridge bis-heptylene sulfonamide compound containing a suberic acid monoanilide group as well as a synthesizing method, application and an anti-breast cancer drug composition of the oxygen bridge bis-heptylene sulfonamide compound. The oxygen bridge bis-heptylene sulfonamide compound containing the suberic acid monoanilide group is prepared by one-step reaction of the following raw materials: 3-(4-hydroxyphenyl)-4-suberic acid monoanilino-furan and an ethenyl sulfonamide derivative at the temperature of 90 DEG C for 3 without a solvent or a catalyst. The oxygen bridge bis-heptylene sulfonamide compound is different from the existing anti-breast cancer drug tamoxifen in action modes and is an anti-breast cancer compound acting on an estrogen receptor and histone histone deacetylase dual target sites.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to oxobisheptene sulfonamide compounds containing suberoyl anilide groups, their synthesis method, application and anti-breast cancer drug composition. Background technique [0002] The small molecule ligands of selective estrogen modulators (SERMs) act on the process of binding estrogen ligands to estrogen receptors, mainly by competing with endogenous estradiol to estrogen receptors Binds to block estradiol-mediated estrogen signaling pathways. Clinically, SERMs such as tamoxifen are useful in the treatment of hormone-dependent (ER + ) patients with breast cancer have achieved better results. However, long-term use often leads to drug resistance, and once drug resistance occurs, SERMs drugs will not only fail to produce tumor-suppressing effects due to their weak estrogen-like effects, but will promote tumor growth instead. Therefore, the problem of resistance to e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08A61K31/341A61P35/00
CPCC07D493/08
Inventor 黄健董春娥唐初李长浩
Owner 武汉宏兹生物技术有限公司
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