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Compound with base skeleton of 1,6-methylene-[10]-annulene and use thereof

A technology of methylene and compounds, which can solve the problems of nearly blank research on biological properties and minimal research on analogues, etc.

Inactive Publication Date: 2003-10-22
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, through literature search, it is known that since American professor Vogel synthesized this type of molecule in 1964, only their physical and chemical properties have been investigated, and the research on their biological properties is almost blank, and the research on their analogues is even more minimal.

Method used

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  • Compound with base skeleton of 1,6-methylene-[10]-annulene and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] The synthesis of embodiment 1 compound 2

[0015] Take 320mg (1mmol) of compound 1, dissolve it in 15mL of anhydrous THF, add 0.22mL (1.5mmol) of 1,5-diazabicyclo[5.4.0]undec-5-ene (1,5 -Diazabicyclo[5.4.0]undec-5-ene), after 30min, add 0.22mL (1.5mmol) HCF 2 CF 2 OCF 2 CF 2 SO 2 F, continue to stir the reaction at 0°C. After 30 min, TLC (P / E=1:1) showed that the starting material spot disappeared. Pass the reaction solution through a thick silica gel column, wash with THF (15 mL), combine the eluents, add 0.74 mL (5 mmol) triethylamine, and reflux the oil bath for reaction. The reaction stopped after 2 hours. After spin-drying, 254 mg of compound 2 was obtained by column chromatography, yield: 80%. Compound 2: C 20 h 28 o 2 (300.44) IR (KBr): ν2927, 2872, 1669, cm -1 1 H-NMR (CDCl 3 , 300MHz): δ0.32(1H, d, J=5Hz, 9-H), 2.48(1H, d, J=18Hz, cp-H),

[0016] 2.85 (1H, d, J = 18Hz, cp-H), 3.27 (1H, t, J = 8Hz, 17-H), 3.36 (3H, s, 17-OMe...

Embodiment 2

[0018] Measured value: C: 79.42%, H: 9.16% Synthesis of Example 2 Compound 3

[0019] Take 100 mg (0.33 mmol) of compound 2 and dissolve in 2.1 mL of acetic acid, add 0.42 mL of acetic anhydride, add 125 mg (0.66 mmol) of p-toluenesulfonic acid, and stir at room temperature for reaction. After 1 hour, add 5 mL of ice water to the reaction solution, stir, a light yellow solid precipitates out, filter with suction, wash the filter cake with water, extract the filtrate with dichloromethane, and extract the solution with water and saturated NaHCO 3 , washed with water; the filter cake was dissolved with dichloromethane and washed twice with water. The extract and solution were combined, dried over anhydrous sodium sulfate, spin-dried, and column chromatographed to obtain 396 mg of the compound, yield: 85%. Compound 3: C 22 h 30 o 2 (342.48)IR(KBr): ν2933, 1747, 1601cm -1 1 H-NMR (CDCl 3 , 300MHz): δ0.40(1H, m, 9-H), 0.91(3H, s, 18-Me), 2.20(3H, s, MeCO-),

[0020] ...

Embodiment 3

[0023] The synthesis of embodiment 3 compound 5

[0024] 0.5 mmol of substrate 4 was dissolved in 10 ml of anhydrous THF. Add 1.5eq. of 1,5-Diazabicyclo[5.4.0]undec-5-ene and 1.5eq. of HCF dropwise under ice-water bath 2 CF 2 OCF 2 CF 2 SO 2 F. After adding, react for 30 minutes. The reaction solution was filtered through a short thick silica gel column, and an equal volume of solvent was rinsed. Combine the washings and filtrates.

[0025] 5eq. of triethylamine was added thereto, heated to reflux, and reacted until the TLC detected raw material point disappeared. The solvent and triethylamine were distilled off under reduced pressure. The residue was separated by column chromatography to obtain the intermediate.

[0026] Add 4.0eq. of 1,5-Diazabicyclo[5.4.0]undec-5-ene and 4.0eq. of HCF 2 CF 2 OCF 2 CF 2 SO 2 F, the reaction solution was filtered through a short thick silica gel column. Solvent rinse. Combine the washings and filtrates....

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Abstract

The present invention relates to a compound with 1,6-methylene-[10]-annulene basic skeleton. Said invention provides its structure formula. Said compound has the activity for inhibiting tumor cell, can be used for developing new anti-tumor medicine for curing cancer of lung, mammary cancer, liver cancer and leukemia, etc.

Description

technical field [0001] This patent relates to a compound with a basic skeleton of 1,6-methylene-[10]-annulene and its application. These compounds were efficiently synthesized using fluorosulfonyl fluoride-induced carbocation rearrangement reactions. This class of compounds has been shown to have anticancer activity and is an antitumor compound. Background technique [0002] In order to discover and develop new drugs, the search for natural or non-natural compounds with special biological activity and unique chemical structure has always been the goal pursued by chemists, biologists and drug manufacturers. To this end, natural product chemists are tirelessly and constantly changing methods to find novel natural compounds with special biological activities and unique chemical structures from the biological world; medicinal chemists and synthetic chemists tirelessly design and synthesize compounds based on the knowledge that humans have acquired. new molecules. Obviously, d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/122A61K31/13A61K31/16C07B61/00C07C43/18C07C49/753C07C69/757C07C309/68C07F9/09
Inventor 田伟生丁凯吴秀静陈玲
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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