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2-(1-adamantanecarboxamido) ethyl formate compound and preparation method and application thereof

A technology for adamantanecarboxamide and ester compounds, which is applied in the field of 2-(1-adamantanecarboxamido)ethyl formate and its preparation and application, and can solve the problems that have not been found in the research of structure and biological activity. Literature reports and other issues, to achieve the effect of simple preparation method

Active Publication Date: 2019-11-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The series of 2-(1-adamantanecarboxamido) ethyl formate 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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  • 2-(1-adamantanecarboxamido) ethyl formate compound and preparation method and application thereof
  • 2-(1-adamantanecarboxamido) ethyl formate compound and preparation method and application thereof
  • 2-(1-adamantanecarboxamido) ethyl formate compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Synthesis of compound Ia (R = phenyl):

[0028] 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).

[0029] The intermediate N-2-hydroxyethyl-1-adamantanecarboxamide (0.335g, 1.5mmol) was mixed with tetrahydrofuran (10mL) and the acid-binding agent triethylamine (1.8mmol), stirred and dissolved, and placed in an ice bath A solution of benzoyl chloride (1.5 mmol) in tetrahydrofuran (5 mL) was slowly added dropwise. After the dropwise addition was completed, react at room temperature for 3 h, then filter to remove the hydrochloride of triethylamine generated by the reaction, remove the solvent tetrahydrofuran by rotary evaporation of the filtrate, and obtain a white solid through column chromatography separation of the obtained rotary evaporation residue (eluent is volume A mixture of ethyl acetate and petroleum ether at a ratio of 1:5) is benzoic acid-2-(1-adamantanecarb...

Embodiment 2

[0032] Example 2 Synthesis of compound Ib (R=2-chlorophenyl):

[0033] The intermediate N-2-hydroxyethyl-1-adamantanecarboxamide (0.335g, 1.5mmol) was mixed with tetrahydrofuran (12mL) and the acid-binding agent triethylamine (2.7mmol), stirred and dissolved, and placed in an ice bath A solution of 2-chlorobenzoyl chloride (2.0 mmol) in tetrahydrofuran (6 mL) was slowly added dropwise. After the dropwise addition was completed, react at room temperature for 4 h, then filter to remove the hydrochloride of triethylamine generated by the reaction, remove the solvent tetrahydrofuran by rotary evaporation of the filtrate, and obtain a white solid through column chromatography separation of the obtained rotary evaporation residue (eluent is volume A mixture of ethyl acetate and petroleum ether at a ratio of 1:4) is 2-(1-adamantanecarboxamido)ethyl 2-chlorobenzoate, and the calculated yield is 65.3%. m.p.:120~123℃;

[0034] 1 H NMR (500MHz, CDCl 3 )δ7.83(dd,J=7.5,1.0Hz,1H),7.49–7...

Embodiment 3

[0036] Example 3 Synthesis of compound Ic (R=3-chlorophenyl):

[0037] The intermediate N-2-hydroxyethyl-1-adamantanecarboxamide (0.335g, 1.5mmol) was mixed with tetrahydrofuran (12mL) and the acid-binding agent triethylamine (2.7mmol), stirred and dissolved, and placed in an ice bath A solution of 3-chlorobenzoyl chloride (2.0 mmol) in tetrahydrofuran (6 mL) was slowly added dropwise. After the dropwise addition was completed, react at room temperature for 3 h, then filter to remove the hydrochloride of triethylamine generated by the reaction, remove the solvent tetrahydrofuran by rotary evaporation of the filtrate, and obtain a white solid through column chromatography separation of the obtained rotary evaporation residue (eluent is volume A mixture of ethyl acetate and petroleum ether at a ratio of 1:3) is 2-(1-adamantanecarboxamido)ethyl 3-chlorobenzoate, and the calculated yield is 52.5%. m.p.:127~130℃;

[0038] 1 H NMR (500MHz, CDCl 3 )δ7.94(s,1H),7.86(d,J=7.5Hz,1H),...

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Abstract

The invention discloses a 2-(1-adamantanecarboxamido) ethyl formate compound and a preparation method and application thereof. The chemical structural formula of the 2-(1-adamantanecarboxamido) ethylformate compound is shown in a formula (I), wherein R is phenyl, substituted phenyl or substituted pyridyl; H on the benzene ring of the substituted phenyl group or H on the pyridine ring of the substituted pyridyl group is monosubstituted or polysubstituted by substituents, and the monosubstituted or polysubstituted substituents are independently selected from C1-C5 alkyl, C1-C3 alkoxy, nitro, C1-C5 haloalkyl or halogen. The preparation method of the 2-(1-adamantanecarboxamido) ethyl formate compound is simple, and the 2-(1-adamantanecarboxamido) ethyl formate compound shows certain anti-tumor activity.

Description

technical field [0001] The invention relates to a 2-(1-adamantanecarboxamido) ethyl formate compound and a preparation method and application thereof. Background technique [0002] Adamantane has unique chemical and physical properties and can be used in medicine (Chemical Reviews, 2013, 113(5): 3516-3604), pesticides (Chemical Reagents, 2016, 38(03): 224-230), optoelectronic materials (Tetrahedron, 2013, 69(48): 10357-10360) 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 are attracting more and more attention from drug developers. In addition, in the field of medicine, adamantane with a...

Claims

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Application Information

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IPC IPC(8): C07D213/803C07D213/80C07D213/79C07C233/60C07C231/12A61P35/00
CPCA61P35/00C07C233/60C07D213/79C07D213/80C07D213/803C07C2603/74
Inventor 翁建全孔瑶蕾庞凯胜刘幸海
Owner ZHEJIANG UNIV OF TECH
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