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Fangchinoline-carbamate derivative with bactericidal activity

A technology of carbamates and fangchinoline base, which is applied in the field of synthesis of fangchinoline-carbamate derivatives, achieving the effect of high yield and novel structure

Active Publication Date: 2019-08-23
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many structural modifications of fangchinoline base, but there is no literature report on the addition reaction of fangchinoline base and isocyanate to obtain fangchinoline base-carbamate derivatives as agricultural fungicides

Method used

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  • Fangchinoline-carbamate derivative with bactericidal activity
  • Fangchinoline-carbamate derivative with bactericidal activity
  • Fangchinoline-carbamate derivative with bactericidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation of embodiment 1 compound I-a

[0046] The compound I-a prepared in this embodiment has the structure shown in the following formula:

[0047]

[0048] Synthetic method: Dissolve tetrandrine (2.53g, 4.16mmol) in dichloromethane (CH 2 Cl 2 ,15mL), then add triethylamine (NEt 3 , 1.26g, 12.47mmol) and ethyl isocyanate (12.47mmol) and the mixture was warmed to room temperature, under N 2 Stir under atmosphere for 24 hours. The reaction mixture was quenched with ice water and washed with dichloromethane (CH 2 Cl 2 , 3×20mL) extraction. The combined organic phases were washed with brine (2×30 mL), and washed over anhydrous sodium sulfate (Na 2 SO 4 ) to dry overnight. After removing the solvent in vacuo, the crude product was chromatographed on silica gel (petroleum ether:ethyl acetate=10:1, v / v) to obtain the target compound I-a.

[0049] The instrument used for infrared spectrum (IR) measurement is the AVATAR 330 type infrared spectrometer (KBr ...

Embodiment 2

[0051] The preparation of embodiment 2 compound I-b~I-1

[0052] The synthetic method of compound I-b~I-l is the same as I-a, wherein ethyl isocyanate is changed into corresponding R 1 group, R 1 They are: propyl, isopropyl, tert-butyl, phenyl, o-methylphenyl, m-methylphenyl, p-methylphenyl, p-methoxyphenyl, p-chlorophenyl, p-trifluoro Methylphenyl, p-trifluoromethoxyphenyl. The physical and chemical properties of the synthesized compounds are shown in Table 1 below.

[0053] The physicochemical property of table 1 compound I-a~I-l

[0054]

[0055] I-a: yellow powdery solid; yield 89%; melting point::154-155°C; IR: 1739 (C=O); HRMS (ESI), m / z: 680.3386[M+H] + (calcd for C 40 h 46 N 3 o 7 :680.3330); 1 H NMR (600MHz, CDCl 3 )δ: 7.29 (1H, dd, J = 8.2, 2.2Hz), 7.13 (1H, dd, J = 8.2, 2.6Hz), 6.90 (1H, d, J = 7.4Hz), 6.85 (1H, d, J =8.2Hz),6.79(1H,dd,J=8.2,2.6Hz),6.51(2H,s),6.34(1H,s),6.24(1H,dd,J=8.2,2.2Hz),5.96(1H ,s),3.92(3H,s),3.81(1H,d,J=7.8Hz),3.74(3H,s),3.72-...

Embodiment 3

[0067] Embodiment 3 preliminary screening test of antibacterial activity

[0068] Tested strains: Gibberella zeae, Phoma adianticola, Phomopsis adianticola, Altermaria alternata, Colletotrichum fructicola, tea tree Pestalotiopsis theae.

[0069] Production medium: Wash and peel the potatoes, cut into pieces, weigh 400g in a container, add water to boil, and keep boiling slightly for 15-20min, stir moderately, and stop heating. Filter in a beaker with three layers of gauze, add 40g of glucose and 40g of agar, stir to dissolve, transfer to a 2000mL volumetric flask and set the volume to 2000mL. Add 198mL of filtrate to ten 250mL Erlenmeyer flasks, wrap them with sterile parafilm, seal them again with newspaper, exhaust the air with a vertical pressure steam sterilizer at 101°C, and sterilize at 121°C for 30 minutes for later use. All required Petri dishes and pipette tips were sterilized under the same conditions and dried for later use.

[0070] Dispensing and inoculation: W...

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Abstract

The invention belongs to the technical field of chemical pesticide synthesis, and particularly relates to a compound fangchinoline-carbamate derivative with bactericidal activity. The compound is prepared by carrying out a one-step addition reaction on natural product fangchinoline with alkyl or aryl isocyanate in dichloromethane and triethylamine at room temperature, and the yield is high. An antibacterial activity screening test proves that the fangchinoline-carbamate derivative has a relatively good inhibition effect on fusarium graminearum or phomopsis spp., and activity of the fangchinoline-carbamate derivative is superior to or equal to activity of bactericidal pesticide azoxystrobin with a relatively large usage amount.

Description

technical field [0001] The invention belongs to the technical field of chemical pesticide synthesis, and specifically relates to a synthesis method and application of fangchinoline-carbamate derivatives with bactericidal activity. Background technique [0002] Tetrandrine (also known as tetrandrine) and fangchinoline (also known as tetrandrine B) are a class of alkaloids extracted from the roots of tetrandrine. Since the structure of fangchinoline was determined by Kupchan et al. in 1973, the research on its pharmacology has also risen thereupon (Kupchan, S M.Recent advances in the chemistry of tumorinhibitors of plant origin..Transactions of the New York Academy of Sciences, 2012, 32(1Series II): 85-106). Fangchinoline has a certain anti-inflammatory effect on rat formaldehyde arthritis, and also has a certain antihypertensive effect (Ji Yubin. Pharmacology and application of active ingredients in traditional Chinese medicine. People's Health Publishing House, 2010); Fangc...

Claims

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Application Information

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IPC IPC(8): C07D491/18A01N47/22A01P3/00
CPCC07D491/18A01N47/22
Inventor 徐胜臻曹敏惠王齐汤保贺
Owner HUAZHONG AGRI UNIV
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