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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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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, rice sheath blight, mango anthracnose, cucumber Phytophthora, watermelon wilt, litchi downy mildew , Strawberry Botrytis and Banana Fusarium wilt

Method used

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  • 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,...

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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

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Application Information

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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
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