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Thiapyran[4,3-b] indole compound and preparing method and application thereof

A compound and indole technology, applied in the field of thiopyran [4,3-b] indole compounds and their preparation, can solve the problems of poor water solubility, cumbersome, limited application, etc.

Active Publication Date: 2018-09-21
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The basic skeleton of dehydrohalline is β-carboline, which belongs to a fully aromatic tricyclic planar structure and has strong rigidity, so the water solubility of this type of compound is very poor, which seriously limits its application in medicine and pesticides. application
Moreover, the synthesis of β-carboline compounds is obtained through Pictet-Spengler reaction, esterification reaction, oxidation reaction and other modification reactions. The reaction steps are lengthy and cumbersome, resulting in low overall yield.

Method used

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  • Thiapyran[4,3-b] indole compound and preparing method and application thereof
  • Thiapyran[4,3-b] indole compound and preparing method and application thereof
  • Thiapyran[4,3-b] indole compound and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Synthesis of β-carbolines

[0046] For the preparation of β-carbolines, see literature methods (Hagen T.J., et al. Journal of Medicinal Chemistry, 1987, 30, 750-753).

Embodiment 2

[0047] Example 2: Synthesis of 2-methyl-2,3,4,5-tetrahydro-1H-pyridine[4,3-b]indole (1)

[0048] Synthetic route 1:

[0049]

[0050] Compounds 1 to 3 were all prepared through synthetic route 1.

[0051] For the preparation method of compound 1, see literature method (Raoul M., et al. Journal of Enzyme Inhibition and Medicinal Chemistry, 2006, 21, 251-260). Phenylhydrazine hydrochloride (1.45 g, 10 mmol) was added to a 100 mL round-bottomed flask, 50 mL of absolute ethanol was added to dissolve, then 1-methyl-4-piperidone (1.13 g, 10 mmol) was added, and the mixture was heated to reflux for 3 h. The completion of the reaction was monitored by TLC, concentrated under reduced pressure, 40 mL of distilled water was added to the residue, adjusted to pH 12-13 with 10% NaOH, then extracted with dichloromethane 3 times, the extracts were combined, washed with water, dried over anhydrous MgSO4, filtered, Concentration under reduced pressure gave the title compound.

Embodiment 3

[0052] Example 3: Synthesis of 2-ethoxycarbonyl-2,3,4,5-tetrahydro-1H-pyridine[4,3-b]indole (2)

[0053] The operation is the same as that in Example 2, except that 1-ethoxycarbonyl-4-piperidinone is used instead of 1-methyl-4-piperidinone. Product detection data are as follows: gray solid, yield 74%. 1 H-NMR (400MHz, CDCl 3 )δ: 7.92(s, 1H, 5-NH), 7.46(d, J=7.8Hz, 1H, 6-H), 7.31(d, J=7.9Hz, 1H, 9-H), 7.16(t, J=7.5Hz, 1H, 8-H), 7.10(t, J=7.4Hz, 1H, 7-H), 4.70(s, 2H, 1-CH 2 -),4.21(q,J=7.1Hz,2H,-O CH 2 CH 3 ),3.88(s,2H,3-CH 2 -),2.85(s,2H,4-CH 2 -),1.31(t,J=7.1Hz,3H,-OCH 2 CH 3 ); anal.calcd for C 14 H 16 N 2 O 2 : C, 68.83; H, 6.60; N, 11.47; found: C, 68.69; H, 6.62; N, 11.32.

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Abstract

The invention discloses a thiapyran[4,3-b] indole compound and a preparing method and application thereof. The structure of the compound is shown in the formula 1, wherein the formula 1 is shown in the description, and R1-R5 are not all hydrogen. The compound has excellent activities of inhibiting mycelial growth, protecting detached leaves, protecting living bodies and treating the living bodiesfor rhizoctonia solani, the effects of the compound are even superior to those of positive control drugs, and the compound has an important application value in preventing and / or treating rice sheathblight.

Description

technical field [0001] The invention belongs to the technical field of pesticides. More specifically, it relates to a thiopyran [4,3-b] indole compound and its preparation method and application. Background technique [0002] Due to the diversity and complexity of structure, biodegradability, environmental friendliness, pest specificity and low toxicity to mammals, natural active molecules have gradually become a research hotspot in the field of pesticides ((1) Dayan et al., Bioorganic & Medicinal Chemistry , 2009, 17, 4022-4034; (2) Rosell et al. Journal of Pesticide Science, 2008, 33, 103-121; (3) Petroski. Journal of Agricultural and Food Chemistry, 2009, 57, 8171-8179; (4) Crombie, Pesticide Science, 1999, 55, 761-774), is expected to replace chemical pesticides, thereby reducing the harm to the environment and human health. In recent years, research on natural source fungicides has received much attention at home and abroad. So far, many natural products have been re...

Claims

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Application Information

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IPC IPC(8): C07D495/04A01N43/90A01P3/00
CPCA01N43/90C07D495/04
Inventor 易欣张智军钟国华刘婕江志彦朱琪
Owner SOUTH CHINA AGRI UNIV
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