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Ferrocenyl amide derivative containing pyrimidine ring and preparation method and appliation thereof

A ferrocene amide and pyrimidine ring technology, applied in the field of ferrocene amide derivatives and their preparation, can solve the problems of drug resistance, increase the risk of blood clots in the lungs, etc., and achieve the effect of inhibiting growth

Inactive Publication Date: 2017-06-30
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Long-term use of breast cancer drug tamoxifen increases risk of blood clots in lungs, develops drug resistance

Method used

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  • Ferrocenyl amide derivative containing pyrimidine ring and preparation method and appliation thereof
  • Ferrocenyl amide derivative containing pyrimidine ring and preparation method and appliation thereof
  • Ferrocenyl amide derivative containing pyrimidine ring and preparation method and appliation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Preparation of (E)-4-chloro-N-(4-chlorobenzyl)-N-(4-ferrocenylvinyl)pyrimidin-2-yl)benzamide (4a)

[0033]

[0034] a. Weigh formyl ferrocene (1) (4.8g, 20mmol) in a 250mL single-necked flask, add acetone (100mL), then dropwise add sodium hydroxide solution (2mL, 2mol / L), stir at room temperature, TLC Detection, stop the reaction when the formylferrocene is consumed, add water until the precipitation is complete, filter with suction, dry, and separate by column chromatography (eluent is ethyl acetate / petroleum ether=1 / 2, v / v), 4.22 g of the intermediate (2) methyl ferrocene vinyl ketone was obtained. Deep red solid, yield 83.7%, melting point: 125-127°C.

[0035] 1 H NMR (CDCl 3 ):δ7.42(d,J=16.0Hz,1H),6.34(d,J=16.0Hz,1H),4.50(s,2H),4.44(s,2H),4.15(s,5H),2.29 (s,3H).MS(ESI):255.1(C 14 h 14 FeO,[M+H] + ).

[0036] b. Weigh the intermediate (2) (254mg, 1mmol) and dissolve it in 3mL dimethylformamide, add 595mg of N,N-dimethylformamide dimethyl acetal,...

Embodiment 2

[0043] Example 2: (E)-4-methoxy-N-(4-methoxybenzoyl)-N-(4-ferrocenylvinyl)pyrimidin-2-yl)benzamide (4b ) preparation

[0044]

[0045] The preparation method of this example is the same as that of Example 1, except that in step c, 4-methoxybenzoyl chloride is used instead of 4-chlorobenzoyl chloride to obtain the target product (4b) (E)-4-methoxy- N-(4-methoxybenzoyl)-N-(4-ferrocenylvinyl)pyrimidin-2-yl)benzamide. Yield: 77%, dark red solid, melting point: 91-93°C.

[0046] 1 H NMR (CDCl 3 ): δ8.48(d, J=5.1Hz, 1H), 7.78(d, J=7.4Hz, 4H), 7.43(d, J=15.6Hz, 1H), 7.38(t, J=8.7Hz, 4H ),6.92(d,J=5.1Hz,1H),6.45(d,J=15.6Hz,1H),4.47(s,2H),4.41(s,2H),4.11(s,5H). 13 C NMR (151MHz, CDCl 3 ): δ174.88, 166.85, 165.72, 163.49, 161.24, 141.93, 134.27, 129.65, 124.16, 117.36, 116.53, 82.79, 73.29, 72.18, 70.87, 58.07, 32.29. 32 h 27 FeN 3 o 4 ,[M+H] + ).

Embodiment 3

[0047] Example 3: (E)-4-methyl-N-(4-methylbenzoyl)-N-(4-ferrocenylvinyl)pyrimidin-2-yl)benzamide (4c) preparation

[0048]

[0049] The preparation method of this example is the same as that of Example 1, except that in step c, 4-methylbenzoyl chloride is used instead of 4-chlorobenzoyl chloride to obtain the target product (4c) (E)-4-methyl-N- (4-methylbenzoyl)-N-(4-ferrocenylvinyl)pyrimidin-2-yl)benzamide. Yield: 77%, dark red solid, melting point: 35-37°C.

[0050] 1 H NMR (CDCl 3 ): δ8.50(d, J=5.2Hz, 1H), 7.77(d, J=8.0Hz, 4H), 7.44(d, J=15.6Hz, 1H), 7.18(d, J=8.0Hz, 4H ),6.88(d,J=5.2Hz,1H),6.44(d,J=15.6Hz,1H),4.46(s,2H),4.38(s,2H),4.08(s,5H),2.34(s ,6H). 13 C NMR (151MHz, CDCl 3 ): δ175.38, 166.78, 163.28, 161.26, 145.96, 141.94, 134.62, 132.07, 131.92, 124.03, 117.50, 82.78, 73.29, 72.17, 70.87, 32.34, 24.30.MS(ESI): 542. 32 h 27 FeN 3 o 2 ,[M+H] + ).

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Abstract

The invention discloses a ferrocenyl amide derivative containing a pyrimidine ring and a preparation method and application thereof. The structure of the ferrocenyl amides derivative containing the pyrimidine ring is as shown in a general formula (1) or a general formula (2) as shown in the specification, wherein R is selected from 4-chlorine, 4-methoxyl, 4-methyl, 3-chlorine, 3,5-dimethoxy, 3,5-dichlorine, 4-ethyl, 4-chlorine, 4-bromine, 3-bromine, 3-methyl, 4-trifloromethoxyl or hydrogen. The ferrocenyl amide derivative containing the pyrimidine ring has an obvious growth inhibiting effect on mice skin melanoma cells (B16-F10) and human lung cancer cell strains (A549), and can be used for preparing antineoplastic pharmaceuticals.

Description

[0001] 1. Technical field [0002] The invention relates to a ferrocene derivative, in particular to a ferrocene amide derivative containing a pyrimidine ring, a preparation method and application thereof. [0003] 2. Background technology [0004] Ferrocene is an orange-yellow prism or powder crystal, chemically named cyclopentadienyl iron, which is composed of two cyclopentadiene and a ferrous ion. An iron atom is sandwiched between the two cyclocene rings. It is a typical type II complex with a sandwich structure. It has aromaticity and a very stable structure. It will not decompose below 470°C. Its chemical properties are similar to those of aromatic compounds, it is not easy to undergo reduction reaction, and it is prone to electrophilic substitution reaction. The structure determines the properties. The particularity of the structure of ferrocene determines that ferrocene and its derivatives have various biological activities, including anti-tumor, anti-anemia, anti-mala...

Claims

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Application Information

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IPC IPC(8): C07F17/02A61K31/555A61P35/00
CPCC07F17/02
Inventor 阮班锋葛为为李青山
Owner HEFEI UNIV OF TECH
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