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Banisterine oxazoline derivate and preparation method and application thereof

A technology for alkali oxazolines and camellias, which is applied in the field of camelid alkali oxazolines derivatives and their preparation, can solve the problems of structure-activity relationship research, lack of in-depth derivatization and synthesis, and few synthetic studies.

Active Publication Date: 2016-08-17
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, at present, there are relatively few studies on the application of salicine compounds as pesticides in plant disease control and agricultural pest control. The research content is mainly on the insecticidal or antibacterial activities of salicine crude extracts and simple derivatives. The preliminary determination of insects, as well as the preliminary discussion of the physiological changes and insecticidal mechanism of insects after feeding on salaline, such as the relevant literature reports ((1) Sun Zhitan, et al. Journal of Hubei Agricultural University, 2004, 24, 85 -89; (2) Weng Qunfang, et al. Chinese Agricultural Sciences, 2005, 38, 2014-2022; (3) Huang Jinfei, et al. Journal of Huazhong Agricultural University, 2010, 29, 31-36; (4) Rharrabe K., et al. Pesticide Biochemistry and Physiology, 2007, 89, 137-145)
However, the current research has not gone deep into the derivation synthesis and structure-activity relationship research of the system.
There are few studies on the synthesis of harmine and its related compounds, and such substances extracted from nature cannot meet a large number of needs at all. Therefore, it is necessary to explore the research of harmine and its related compounds and their artificial synthesis methods. The application is significant

Method used

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  • Banisterine oxazoline derivate and preparation method and application thereof
  • Banisterine oxazoline derivate and preparation method and application thereof
  • Banisterine oxazoline derivate and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Example 1: Synthesis of 1-methyl-3-[5-(2-mercapto)-1,3,4-oxazoline]-β-carboline (6a)

[0095] 1. Add 2.4g of 1-methyl-β-carboline-3-hydrazide to a 50mL round bottom flask, and add 10mL of ethanol to dissolve it. Under ice bath, add 0.56g of potassium hydroxide and 3mL of Carbon disulfide was slowly heated to reflux for 48 hours, and the reaction progress was tracked by thin-layer chromatography. After the reaction, concentrate under reduced pressure to remove the solvent, add 10 mL of distilled water to dissolve the residue, adjust the pH to acidic with dilute hydrochloric acid solution, filter, wash the residue with water, recrystallize with methanol, and dry to obtain the product.

[0096] 2. The product detection data is as follows: Yield: 65%; 1 H NMR (600MHz, DMSO-d 6 )δ:12.09(s,1H,9-NH),8.71(s,1H,4-H),8.40(d,J=7.9Hz,1H,5-H),7.66(d,J=8.2Hz, 1H,8-H),7.61(t,J=7.6Hz,1H,7-H),7.31(t,J=7.7Hz,1H,6-H),2.85(s,3H,1-CH 3 ). 13 C NMR (151MHz, DMSO-d 6 )δ: 177.90, 161.71,...

Embodiment 2

[0097] Example 2: Synthesis of 1-phenyl-3-[5-(2-mercapto)-1,3,4-oxazoline]-β-carboline (6b)

[0098] 1. The operation is the same as in Example 1, except that 1-methyl-β-carboline-3-hydrazide is replaced by 1-phenyl-β-carboline-3-hydrazide.

[0099] 2. The product detection data is as follows: Yield: 78%; 1 H NMR (600MHz, DMSO-d 6 )δ:11.99(s,1H,9-NH),8.88(s,1H,4-H),8.48(d,J=7.9Hz,1H,5-H),8.06(d,J=7.1Hz, 2H,8,4'-H),7.71(d,J=8.2Hz,1H,Ar-H),7.67(t,J=7.6Hz,2H,Ar-H),7.64-7.58(m,3H, Ar-H,7-H),7.35(t,J=7.2Hz,1H,6-H). 13 C NMR (151MHz, DMSO-d 6 )δ: 178.05, 161.60, 143.27, 142.06, 137.63, 134.48, 131.38, 129.99, 129.68, 129.43, 129.35, 129.08, 122.70, 121.34, 120.95, 114.39, 113.27.

Embodiment 3

[0100] Example 3: Synthesis of 1-p-methylphenyl-3-[5-(2-mercapto)-1,3,4-oxazoline]-β-carboline (6c)

[0101] 1. The operation is the same as in Example 1, except that 1-methyl-β-carboline-3-hydrazide is replaced by 1-p-methoxyphenyl-β-carboline-3-hydrazide.

[0102] 2. The product testing data is as follows: Yield: 69%; 1 H NMR (600MHz, DMSO-d 6 )δ:11.92(s,1H,9-NH),8.82(s,1H,4-H),8.44(d,J=7.4Hz,1H,5-H),7.95(d,J=7.3Hz, 2H,8-H,Ar-H),7.70(d,J=8.0Hz,1H,Ar-H),7.64-7.58(m,1H,7-H),7.46(d,J=7.3Hz,2H ,Ar-H),7.35-7.31(m,1H,6-H),2.46(s,3H,4′-CH 3 ). 13 C NMR (151MHz, DMSO-d 6 )δ: 161.65, 143.36, 142.03, 139.24, 134.87, 134.41, 131.39, 129.89, 129.35, 128.96, 122.64, 121.37, 120.90, 114.14, 113.27, 21.44.

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Abstract

The invention discloses a banisterine oxazoline derivate and a preparation method and application thereof. The structural formula of the banisterine oxazoline derivate is shown in the formula (I), wherein R1 is methyl or phenyl or p-methylphenyl or p-chlorophenyl or p-bromophenyl or p-trifluoromethylphenyl or p-methoxyphenyl or 3,4,5-triethoxy phenyl or o-chlorophenyl or m-chlorobenzene or 2-naphthyl; R2 is sulfydryl or hydroxyl or azyl or ethyl or cyclopropyl or phenyl or p-methylphenyl or p-chlorphenyl. The derivate can have the remarkable cytotoxic activity for spodoptera frugiperda cell free system Sf9, and has the remarkable inhibitory activity for rhizoctonia solani. The banisterine oxazoline derivate is simple in structure, easy to synthesize, simple in synthesis technology, high in product purity and suitable for large-scale industrial production and has the good application prospect.

Description

technical field [0001] The invention belongs to the technical field of pesticides. More specifically, it relates to a oxazoline derivative of camelamine 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 Chemistr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A01N43/90A01P3/00A01P7/04
CPCA01N43/90C07D471/04
Inventor 钟国华张智军张菁翁群芳张晶晶
Owner SOUTH CHINA AGRI UNIV