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

Naphthoquinone multi-fused-ring derivative as well as preparation method and application thereof

A derivative, naphthoquinone technology, applied in the field of medicinal chemistry, can solve the problems of harsh reaction conditions, pre-functionalization, etc., and achieve the effects of simple operation, low cost, and wide substrate adaptability

Active Publication Date: 2021-11-30
XIHUA UNIV
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing synthetic methods mainly have the following problems: (1) pre-functionalization is required; (2) the target product needs to be synthesized through multi-step reactions; (3) expensive metal catalysts are used, and the reaction conditions are relatively harsh

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
  • Naphthoquinone multi-fused-ring derivative as well as preparation method and application thereof
  • Naphthoquinone multi-fused-ring derivative as well as preparation method and application thereof
  • Naphthoquinone multi-fused-ring derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0036] Second, the invention provides a method for preparing naphthoquinone polycyclic derivatives, comprising the steps of:

[0037] Naphthoquinone, indole and maleimide are put into a reaction vessel, and then a catalyst and a solvent are added, and the naphthoquinone polycyclic derivatives are obtained through reaction, separation and purification.

[0038] In the present invention, the chemical reaction formula is,

[0039]

[0040] In the present invention, the molar ratio of naphthoquinone, indole and maleimide is 1:0.5-3:0.5-4.

[0041] In the present invention, the molar ratio of naphthoquinone to catalyst is 1:0.01-0.5.

[0042] In the present invention, the catalyst includes TsOH·H 2 O, CuSO 4 ·5H 2 O, Cu(OTf) 2 , Ni(OTf) 2 , Pd(OAc) 2 、Fe(acac) 3 , FeCl 3 , HCl, B(C 5 f 6 ) 3 、CoCl 2 、Ni(acac) 2 、C 6 h 5 B(OH) 2 , BF 3 ·OEt 2 at least one of the

[0043] In the present invention, the solvent includes EtOH, H 2 O, THF, toluene, (CH 2 Oh) 2 ,...

Embodiment 1

[0048] Synthesis of embodiment 1 naphthoquinone polycyclic derivative 4a

[0049]

[0050]Add 47.4mg 1,4-naphthoquinone, 39.3mg N-methylindole, 52mg N-phenylmaleimide, 7.7mg tris(pentafluorophenyl)borane, and then add 3mL acetonitrile to the reaction flask , reacted at 100°C for 24h, cooled to room temperature, added saturated saline, extracted with dichloromethane, combined the organic phases, extracted with anhydrous magnesium sulfate, and obtained red solid 4a by column chromatography with a yield of 80%.

[0051] Red solid, melting point: 282-283°C. 1 H NMR (400MHz, DMSO-d 6 ):δ9.14(d, J=8.0Hz,1H),8.21–8.15(m,2H),7.88–7.81(m,2H),7.47(ddd,J=8.3,7.2,1.2Hz,1H), 7.33–7.22(m,6H),6.89(d,J=8.4Hz,1H),6.75(t,J=7.6Hz,1H),6.65–6.57(m,4H),4.28(d,J=8.5Hz ,2H),4.05(d,J=8.5 Hz,2H),3.42(s,3H). 13 C NMR (101MHz, DMSO-d 6 ): δ194.1, 178.5, 174.7, 172.0, 159.0, 153.5, 137.3, 136.0, 135.4, 135.2, 134.1, 131.7, 129.7, 129.5, 129.1, 127.8, 126.7, 126.6, 118.5, 1167.4, 2, 191 46.0, 41....

Embodiment 2

[0052] The synthesis of embodiment 2 naphthoquinone polycyclic derivatives 4b

[0053]

[0054] Add 47.4mg of 1,4-naphthoquinone, 35.1mg of indole, 52mg of N-phenylmaleimide, 15.4mg of tris(pentafluorophenyl)borane to the reaction bottle, then add 3mL of acetonitrile, and react at 120°C After 24 hours, after cooling to room temperature, saturated saline was added, and then extracted with dichloromethane. The organic phases were combined, extracted with anhydrous magnesium sulfate, and column chromatography gave a red solid 4b with a yield of 54%.

[0055] Orange solid, melting point: 208-210°C. 1 H NMR (400MHz, CDCl 3 ):δ9.22(d, J=8.2Hz, 1H), 8.37–8.32(m, 1H), 8.29–8.24(m, 1H), 7.77–7.71(m, 2H), 7.46(t, J=7.7 Hz, 1H), 7.23(dd, J=6.8, 4.4Hz, 6H), 7.01(d, J=8.2Hz, 1H), 6.95(t, J=7.7Hz, 1H), 6.70(dd, J=6.7 , 2.9Hz, 4H), 5.93(s, 1H), 4.14(d, J=8.7Hz, 2H), 3.58(d, J=8.7Hz, 2H).13C NMR (101MHz, CDCl 3 ): δ 193.9, 179.0, 173.3, 171.1, 158.6, 153.3, 136.9, 135.8, 135.0, 134.9...

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 relates to the technical field of medicinal chemistry, and discloses a naphthoquinone multi-fused-ring derivative as well as a preparation method and application thereof. The structural general formula of the naphthoquinone multi-fused-ring derivative is as shown in formula I, wherein R1 is Ph-, Br-, OH- or H-, R2 is -OMe, Me-, -CN, -NO2, F-, Cl-, Br-, H- or -COOH, R3 is alkyl, alkylene and benzyl, the number of carbon atoms of the alkyl is 1-4, and the number of carbon atoms of the alkylene is 3-4, R4=R5=alkyl or substituted alkyl, aryl, substituted aryl or heteroaryl, and the number of carbon atoms of the alkyl is 1-6, or R4 is a cyclohexyl group, and R5 is H or phenyl. The naphthoquinone multi-fused-ring derivative prepared by the invention has certain biological activity, can be used as a potential drug or a candidate drug molecule for research in the aspects of cancer resistance, tumor resistance, inflammation resistance, bacteria resistance and the like, has good photophysical properties, and can be applied to the field of fluorescent materials.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to naphthoquinone polycyclic derivatives, a preparation method and an application thereof. Background technique [0002] 1,4-Naphthoquinone is a structural scaffold widely distributed in natural products and medicines. Some polycyclic compounds containing quinone structures have attracted widespread attention from synthetic chemists due to their anti-cancer, anti-inflammatory, anti-malarial and other biological activities, such as (1) Calotrixin B isolated from the cyanobacterium Calothrix It has the biological activity of antimalarial and killing Hela cancer cells; (2) Kinamycin series natural products have the effect of anti-cancer cell proliferation; (3) Jorunnamycin A, a marine natural product, exhibits significant growth inhibition on human colon and breast cancer cell lines Function; (4) Streptomyces metabolic isolate Hygr ℃ins has anti-inflammatory ac...

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): C07D487/18C09K11/06A61P35/00A61P29/00A61P31/00
CPCC07D487/18C09K11/06A61P35/00A61P29/00A61P31/00C09K2211/1077C09K2211/1007C09K2211/1029C09K2211/1092Y02A50/30
Inventor 王继宇汪蓓
Owner XIHUA UNIV
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