Synthesis method of compounds of 5-benzoyl-1, 4-naphthaquinone with similar gossypol effect

A benzoyl and synthetic method technology, applied in the field of 5-benzoyl-1, can solve the problems of troublesome post-processing, a large amount of waste water, unfavorable preparation, etc., and achieve stable physical and chemical properties, mild reaction conditions, and reasonable reaction route selection Effect

Inactive Publication Date: 2012-07-18
SOUTHEAST UNIV
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The actual yield of the oxidation step of the method is very low and there are many by-products, and the CrO used in the reaction 3 It has

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
  • Synthesis method of compounds of 5-benzoyl-1, 4-naphthaquinone with similar gossypol effect
  • Synthesis method of compounds of 5-benzoyl-1, 4-naphthaquinone with similar gossypol effect
  • Synthesis method of compounds of 5-benzoyl-1, 4-naphthaquinone with similar gossypol effect

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0039] The preparation method of the formula (VIII) compound compound 5-benzoyl-1,4-naphthoquinone with gossypol-like effect of the present invention comprises the following steps:

[0040]

[0041] (a), malonic acid and acrolein obtain formula (I) compound pentadienoic acid through condensation reaction;

[0042] (b), the ring-closing reaction between the compound of formula (I) and p-benzoquinone to obtain the compound of formula (II) cis 5,8-diketone-1,4,6,7,9,10-hexahydronaphthalene-β-carboxyl acid,

[0043]

[0044] (c), formula (II) compound obtains formula (III) compound 5,8-dimethoxy-1,4-dihydronaphthalene-1-carboxylic acid methyl ester after methylation,

[0045]

[0046] (d), formula (III) compound obtains formula (IV) compound 5,8-dimethoxy naphthoic acid methyl ester through dehydroaromatization reaction,

[0047]

[0048] (e), formula (IV) compound hydrolysis obtains formula (V) compound 5,8-dimethoxy naphthoic acid,

[0049]

[0050] (f), formul...

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 practical synthesis method of compounds of 5-benzoyl-1, 4-naphthaquinone with a similar gossypol effect. The practical synthesis method comprises the steps that: a) malonic acid and acrolein take condensation reaction to obtain a compound of pentadienoic acid shown in the formula I; b) the compound shown in the formula I takes reaction with p-benzoquinone to obtain a compound of cis-5, 8-diketone-1,4,6,7,9,10-hexahydronaphthalene-beta-carboxylic acid shown in the formula II; c) the compound shown in the formula II is subjected to methylation to obtain a compound of 5,8-dimethoxy-1,4-dihydronaphthalene-1-carboxylic acid-methyl ester shown in the formula III; d) the compound shown in the formula III takes dehydro-aromatization reaction to obtain a compound of 5,8-dimethoxy naphthoate shown in the formula IV; e) the compound shown in the formula IV is hydrolyzed to obtain a compound of 5,8-dimethoxy naphthoyl naphthoic acid shown in the formula V; f) the compound shown in the formula V is subjected to chlorination to obtain a compound of 5,8-dimethoxy naphthoyl chloride shown in the formula VI; g) the compound shown in the formula VI and benzene are subjected to Friedel-Crafts acidylation to obtain a compound of 5-benzoyl-1,4-dimethoxy naphthalene shown in the formula VII; and h) the compound shown in the formula VII is oxidized to obtain a compound of 5-benzoyl-1,4-naphthoquinone shown in the formula VIII.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a method for synthesizing 5-benzoyl-1,4-naphthoquinone compounds with gossypol-like effects Background technique [0002] Gossypol (gossypol) is a yellow polyphenolic toxic substance in cotton plants, and its chemical structure is 8,8'-dihydroxyaldehyde-1,1',6,6',7,7'-hexahydroxy -5,5'-diisopropyl-3-3'-dimethyl-2,2'-binaphthyl, with a molecular weight of 518.54. [0003] In the 1960s, Chinese scientists first discovered that gossypol had a definite anti-spermogenic effect, which once triggered an upsurge in research on the anti-fertility effect of gossypol. However, taking gossypol for a long time can cause hypokalemia and irreversible infertility. The above two toxic and side effects greatly limit the promotion and application of gossypol as a male birth control drug, and also interrupt most of the research on gossypol . In addition to having significant male anti-fertility...

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
IPC IPC(8): C07C50/38C07C46/02
Inventor 吉民蔡进李勇李锐
Owner SOUTHEAST UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap