1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as well as synthesis method and application thereof

A technology of adamantane carboxylate and benzoyloxy, which is applied in the field of 1-adamantane carboxylate-2-ethyl ester compounds and their synthesis, and can solve the problems of structure and biological activity that have not been reported in the literature. achieve the effect of simple preparation

Active Publication Date: 2019-11-22
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The series of 1-adamantanecarboxylic acid-2-(substituted benzoyloxy)ethyl ester compounds designed and synthesized by the present invention have no literature reports on their structure and biological activity research

Method used

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  • 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as well as synthesis method and application thereof
  • 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as well as synthesis method and application thereof
  • 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as well as synthesis method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthesis of embodiment 1 compound Ia (R (n)=H):

[0027] Dissolve 1.5 mmol of benzoyl chloride in 5 mL of tetrahydrofuran to prepare a tetrahydrofuran solution (5 mL) of benzoyl chloride (1.5 mmol).

[0028] The intermediate 2-hydroxyethyl-1-adamantanecarboxylate (0.336g, 1.5mmol), tetrahydrofuran (10mL) and acid-binding agent triethylamine (1.8mmol) were mixed, stirred and dissolved, and gradually dissolved in an ice bath. A solution of benzoyl chloride (1.5 mmol) in tetrahydrofuran (5 mL) was slowly added dropwise. After the dropwise addition, react at room temperature for 2 h, then filter to remove the hydrochloride of triethylamine generated by the reaction, and the filtrate is subjected to rotary evaporation to remove solvent tetrahydrofuran, and the obtained rotary evaporation residue is separated by column chromatography (eluent is a volume ratio of 1: The mixed solution of ethyl acetate and petroleum ether in 5) to obtain a light yellow oily liquid, which ...

Embodiment 2

[0031] The synthesis of embodiment 2 compound Ib (R (n)=o-fluorine):

[0032] The intermediate 2-hydroxyethyl-1-adamantanecarboxylate (0.336g, 1.5mmol), tetrahydrofuran (8.5mL) and the acid-binding agent triethylamine (2.25mmol) were mixed, stirred and dissolved, and placed in an ice bath A solution (4 mL) of o-fluorobenzoyl chloride (1.5 mmol) in tetrahydrofuran was slowly added dropwise. After the dropwise addition, react at room temperature for 3h, then filter to remove the hydrochloride of triethylamine generated by the reaction, and the filtrate is subjected to rotary evaporation to remove solvent tetrahydrofuran, and the obtained rotary evaporation residue is separated by column chromatography (eluent is a volume ratio of 1: 3 (mixture of ethyl acetate and petroleum ether) to obtain a white waxy solid, that is, 1-adamantanecarboxylic acid-2-(2-fluorobenzoyloxy)ethyl ester, and the calculated yield was 64.9%.

[0033] 1 H NMR (500MHz, CDCl 3 )δ7.97–7.90(m,1H),7.57–7.51...

Embodiment 3

[0035] Synthesis of Example 3 Compound Ic (R (n) = p-fluorine):

[0036] The intermediate 2-hydroxyethyl-1-adamantanecarboxylate (0.336g, 1.5mmol), tetrahydrofuran (8.5mL) and acid-binding agent triethylamine (2.0mmol) were mixed, stirred and dissolved, and placed in an ice bath A tetrahydrofuran solution (4 mL) of p-fluorobenzoyl chloride (1.5 mmol) was slowly added dropwise. After the dropwise addition, react at room temperature for 3h, then filter to remove the hydrochloride of triethylamine generated by the reaction, and the filtrate is subjected to rotary evaporation to remove solvent tetrahydrofuran, and the obtained rotary evaporation residue is separated by column chromatography (eluent is a volume ratio of 1: 3 mixed solution of ethyl acetate and petroleum ether) to obtain a white waxy solid, which is 2-(4-fluorobenzoyloxy)ethyl 1-adamantanecarboxylate, and the calculated yield is 55.7%.

[0037] 1 H NMR (500MHz, CDCl 3 )δ8.09–8.04(m,2H),7.16–7.10(m,2H),4.52(t,J=4....

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Abstract

The invention discloses a 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound as well as a synthesis method and application thereof, and the structural formula of the 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound is shown as a formula (I): in the formula (I), H on a benzene ring is mono-substituted, di-substituted or unsubstituted by a substituent R; n is an integer from 0 to 2, preferably an integer from 1 to 2, and n represents the number of substituents R on a benzene ring; when n is equal to 0, H on the benzene ring is not substituted;when n is equal to 1, H on a benzene ring is monosubstituted by the substituent R; when n is equal to 2, H on a benzene ring is disubstituted by the substituent R, and the substituents R at differentsubstitution positions are the same or different; the substituent R is hydrogen, alkoxy with 1-3 carbon atoms, haloalkyl with 1-2 carbon atoms, halogen, preferably hydrogen, methoxyl, ethyoxyl, trifluoromethyl, F, Cl or Br. The synthesis method of the 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound is simple, and the compound has certain antitumor activity.

Description

technical field [0001] The invention relates to a 1-adamantanecarboxylic acid-2-(substituted benzoyloxy) ethyl ester compound and a synthesis method and application thereof. Background technique [0002] Adamantane has unique chemical and physical properties, and has been widely used in medicine (Chemical Reviews, 2013, 113(5): 3516-3604), pesticides (Chemical Reagents, 2016, 38(03): 224-230), photoelectric Materials (Tetrahedron, 2013, 69(48): 10357-10 360) and other fields. According to literature reports, adamantane derivatives have antitumor (Investigational New Drugs, 2009, 27 (6): 586-594, Applied Chemistry, 2018, 35 (4): 420-426), antiviral (Journal of Infectious Diseases, 1989,159(3):430-435, Chinese Journal of New Drugs, 2016,25(7):798-803), antidepressant (Journal of Lanzhou University, 1984,37(3):66-76, Biochemical Engineering, 2017, 3(01):70-72) and other biological activities have attracted extensive attention from drug developers. In addition, adamantane is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/14C07C69/78C07C69/76C07C69/92A61P35/00
CPCC07C67/14C07C69/78C07C69/76C07C69/92A61P35/00C07C2603/74
Inventor 翁建全孔瑶蕾庞凯胜刘幸海
Owner ZHEJIANG UNIV OF TECH
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