Harmaline oxazoline compound and preparation method and application thereof

A technology for alkali oxazoline and camelina, which is applied in the field of camelina oxazoline compounds and preparation thereof, and achieves the effects of good growth and development regulating activity, simple synthesis process and simple structure

Active Publication Date: 2016-08-10
SOUTH CHINA AGRI UNIV
View PDF6 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, there are no such compounds and their effectiveness in preventing and controlling Spodoptera litura, Culex fusilicus, radish aphid...

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
  • Harmaline oxazoline compound and preparation method and application thereof
  • Harmaline oxazoline compound and preparation method and application thereof
  • Harmaline oxazoline compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis of 1-methyl-3-[5-(2-o-hydroxyphenyl)-3-N-acetyl-1,3,4-oxazoline]-β-carboline (7a)

[0049] 1. Preparation method

[0050] (1) Step A: Synthesis of 1-methyl-β-carboline-3-o-hydroxybenzoylhydrazone

[0051] Take 0.5g of 1-methyl-β-carboline-3-hydrazide in a 50mL single-necked bottle, add 10mL of absolute ethanol, add 0.27g of o-hydroxybenzaldehyde into the bottle while stirring, add 1mL of glacial acetic acid at the same time, heat to reflux After 2 hours, most of the solvent was removed by rotary evaporation, and the remaining suspension was recrystallized with dilute ethanol, filtered, and dried to obtain 1-methyl-β-carboline-3-o-hydroxybenzoylhydrazone with a yield of 93%;

[0052] (2) Step B: 1-methyl-3-[5-(2-o-hydroxyphenyl)-3-N-acetyl-1,3,4-oxazoline]-β-carboline (7a) Synthesis

[0053] Weigh 0.8g of 1-methyl-β-carboline-3-o-hydroxybenzoylhydrazone and add it to a 50mL round bottom flask installed on a magnetic stirrer, add 10mL of acetic anh...

Embodiment 2

[0056] Example 2: Synthesis of 1-phenyl-3-[5-(2-o-hydroxyphenyl)-3-N-acetyl-1,3,4-oxazoline]-β-carboline (7b)

[0057] 1. Preparation method

[0058] The operation is the same as in Example 1, except that in step A, 1-methyl-β-carboline-3-hydrazide is replaced by 1-phenyl-β-carboline-3-hydrazide.

[0059] 2. The product testing data is as follows:

[0060] Yield: 67%; 1 H NMR (600MHz, DMSO-d 6 )δ: 11.91 (s, 1H, 9-NH), 8.95 (s, 1H, 2′-H), 8.76 (s, 1H, 4-H), 8.44 (d, J=7.8Hz, 1H, 5- H), 8.19(d, J=18.6Hz, 1H, 8-H), 8.00(t, J=8.4Hz, 2H, Ar-H), 7.72(m, 1H, Ar-H), 7.68(t, J=12.6Hz, 1H, A-H), 7.63(t, J=15.6Hz, 2H, Ar-H), 7.60(d, J=16.2Hz, 1H, 7-H), 7.56(d, J=17.4Hz ,1H,Ar-H),7.34(d,J=13.6Hz,1H,Ar-H),7.31(t,J=7.2Hz,1H,6-H),6.80(d,J=3.6Hz,1H ,Ar-H),6.53(s,1H,Ar-H),1.91(s,3H,3′-COCH 3 ). 13 C NMR (151MHz, DMSO-d 6 )δ:169.56,169.44,160.76,148.96,148.53,143.11,141.45,138.07,138.00,135.22,131.16,130.92,130.25,129.98,129.65,128.88,127.77,126.60,126.44,123.74,122.47,122.25,121.01,12...

Embodiment 3

[0061] Example 3: 1-p-chlorophenyl-3-[5-(2-o-hydroxyphenyl)-3-N-acetyl-1,3,4-oxazoline]-β-carboline (7c) Synthesis

[0062] 1. Preparation method

[0063] The operation is the same as in Example 1, except that in step A, 1-methyl-β-carboline-3-hydrazide is replaced by 1-p-chlorophenyl-β-carboline-3-hydrazide.

[0064] 2. The product testing data is as follows:

[0065] Yield: 70%; 1 H NMR (600MHz, DMSO-d 6)δ: 11.97(s,1H,9-NH),11.91(s,1H,OH),9.00(s,1H,2′-H),8.69(s,1H,4-H),8.48(d, J=7.9Hz, 1H, 5-H), 8.24(d, J=8.5Hz, 2H, Ar-H), 7.90(dd, J=7.8, 1.4Hz, 1H, Ar-H), 7.73(d, J=8.5Hz, 2H, Ar-H), 7.70(d, J=8.1Hz, 1H, 8-H), 7.63(t, J=7.6Hz, 1H, 7-H), 7.49(td, J= 7.9,1.6Hz,1H,Ar-H),7.40(t,J=7.3Hz,1H,Ar-H),7.35(t,J=7.5Hz,1H,6-H),7.22(d,J= 7.3Hz,1H,Ar-H),2.46(s,3H,3′-COCH 3 ). 13 C NMR (151MHz, DMSO-d 6 )δ:169.49,161.34,156.97,148.89,143.79,141.57,139.68,138.99,136.06,134.51,133.78,130.91,130.33,130.05,128.82,128.79,128.10,126.77,126.32,125.86,123.49,122.14,121.09,120.40 , 114.44,...

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

PropertyMeasurementUnit
Diameteraaaaaaaaaa
Login to view more

Abstract

The invention discloses a harmaline oxazoline compound and a preparation method and application thereof .The structural formula of the harmaline oxazoline compound is shown as the formula (I) in the description, wherein in the formula (I), R1 is methyl or phenyl or p-chlorophenyl or o-hydroxybenzyl, and R2 is o-hydroxybenzyl or 3-methoxy-4-hydroxyphenyl or 3,5-dimethyl-4-hydroxyphenyl or 2-furyl .The compound has significant cytotoxic activity on spodoptera frugiperda cultured cell lines Sf9, has good insecticidal activity on culex fatigans and lipaphis erysimi, has good growth and development regulating activity on prodenia litura, and also has good inhibitory activity on rhizoctonia solani, colletotrichum gloeosporioides, phytophoria melonis, fusarium oxysporum f .sp .niveum, pseudoperonospora sp, botrytis cinerea and fusarium oxysporum f.sp.cubense .Besides, the compound is simple in structure, easy to synthesize, simple in synthetic process, high in product purity and suitable for large-scale industrial application and popularization.

Description

technical field [0001] The invention belongs to the technical field of pesticides. More specifically, it relates to a haceline oxazoline compound and its preparation method and application. Background technique [0002] Cameline is a kind of β-carboline alkaloid extracted from Peganumharmala L., a plant of Tribulus terrestae in my country. It has various biological activities such as anticancer, insecticidal, bacteriostatic and antiviral, and is more It has attracted the attention of researchers at home and abroad. In recent years, the research on salaline mainly focuses on the anti-tumor aspect, and has carried out in-depth research on structural modification, anti-tumor structure-activity relationship, mechanism of action, etc. ((1) Pan Qichao, etc. Cancer, 1985, 4, 192 -194; (2) Cao Jun, et al. Cancer, 1993, 12, 214-216; (3) Amy M.D., et al. Bioorganic & Medicinal Chemistry Letters, 2001, 11, 1251-1255; (4) Cao R.H., et al . European Journal of Medicinal Chemistry, 2005...

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): C07D471/04A01N43/90A01P7/04A01P3/00
CPCA01N43/90C07D471/04
Inventor 钟国华张智军崔高峰孙冉冉胡美英曾勇
Owner SOUTH CHINA AGRI 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