Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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
View PDF8 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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

Examples

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....

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com