7-acylhydrazone-cyclopentene pyridine compound, preparation method and application thereof, pharmaceutical composition and application thereof

By synthesizing 7-acylhydrazone-cyclopentenylpyridine compounds, the problem of insufficient anti-TMV activity of maltaldehyde was solved, and highly effective insecticides, fungicides, herbicides and antiviral drugs were prepared, which are suitable for industrial production.

CN120647578APending Publication Date: 2025-09-16INSTITUTE OF APPLIED CHEMISTRY JIANGXI ACADEMY OF SCIENCES
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Patent Information

Application Number
CN202510791096.6
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-06-13
Publication Date
2025-09-16

AI Technical Summary

Technical Problem

The existing sea mango aldehyde's anti-TMV activity is not high enough, and the natural active substance is unstable in the environment, with problems such as toxicity, insecticidal spectrum and photostability.

Method used

7-Acylhydrazone-cyclopentenopyridine compounds are synthesized by inserting an acylhydrazone group into the 7-position of cyclopentenopyridine to form a special Schiff base structure containing a -CONHN=C- substructure, and then performing a condensation reaction to prepare the compound.

Benefits of technology

The anti-TMV activity of the compounds was improved, and they had a wide range of biological activities, such as insecticide, antibacterial, weed control, anti-HIV and anti-cancer, especially good insecticidal activity against the larvae of the diamondback moth. The biological activity of many compounds was higher than that of ribavirin, and they showed fungicidal activity against plant pathogens.

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Abstract

The invention provides a 7-acylhydrazone-cyclopentene pyridine compound, a preparation method and application thereof, a pharmaceutical composition and application thereof, and relates to the technical field of medicines. According to the invention, an acylhydrazone group with pesticide activity is connected to the 7th site of cyclopentene pyridine to obtain the cyclopentene pyridine compound containing an acylhydrazone active fragment. The 7-acylhydrazone-cyclopentene pyridine compound provided by the invention contains a special Schiff base structure of a-CONHN = C-substructure, and an acylhydrazone group contains oxygen atoms and nitrogen atoms at the same time, can participate in formation of hydrogen bonds in organisms, has certain flexibility, is firmer in combination with receptors, has wide biological activity, and can be used for preparing a novel compound for preparing the 7-acylhydrazone-cyclopentene pyridine compound. And the compound has good application prospects in preparation of insecticides, bactericides, herbicides, anti-HIV drugs, anti-virus drugs or anti-cancer drugs, especially in plant protection, for example, the compound has good application prospects in preparation of insecticides, bactericides, herbicides, anti-virus drugs, anti-HIV drugs or anti-cancer drugs.
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Claims

1. A 7-acylhydrazone-cyclopentapyridine compound having the structure shown in Formula I: in, X includes oxygen or sulfur; R includes hydrogen, alkyl, amino, unsubstituted or substituted aromatic group; R' includes hydrogen, alkyl or acyl group; when R and R' are not hydrogen at the same time, R and R' may form a ring or not.

2. The 7-acylhydrazone-cyclopentapyridine compound according to claim 1, wherein The aromatic group includes phenyl, naphthyl or N-heterocyclic group; The substituents in the substituted aromatic group include one or more of an alkyl group, a halogen group, an alkoxy group and a hydroxyl group.

3. The 7-acylhydrazone-cyclopentapyridine compound according to claim 1 or 2, characterized in that: The alkyl groups in R and R' independently include C1 to C6 alkyl groups; The alkoxy group includes C1 to C6 alkoxy groups.

4. The 7-acylhydrazone-cyclopentapyridine compound according to claim 2, wherein The N-heterocyclic group includes pyridyl, pyrazinyl, isoquinolyl or quinolyl.

5. The 7-acylhydrazone-cyclopentapyridine compound according to claim 1, 2 or 4, characterized in that: The substituted aryl group includes benzyl, 1-naphthylmethyl, 4-methoxyphenyl, 4-dimethylaminophenyl, 4-methylphenyl, 4-hydroxyphenyl, 4-bromophenyl, 4-nitrophenyl, 4-trifluoromethylphenyl, 4-fluorophenyl, 4-chlorophenyl, 2-fluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-dichlorophenyl, 2-pyridyl, 2-(5-chloropyridyl)yl, 3-pyridyl, 4-pyridyl, 2-pyrazinyl, 2-(5-methoxypyrazinyl), 3-isoquinolyl or 7-quinolyl.

6. The 7-acylhydrazone-cyclopentapyridine compound according to claim 1, characterized in that The ring formed when R and R' form a ring includes an N-heterocycle, and the N-heterocycle includes a five-membered N-heterocycle or a six-membered N-heterocycle.

7. A method for preparing the 7-acylhydrazone-cyclopentapyridine compound according to any one of claims 1 to 6, comprising the following steps: Compound 2, a hydrazide compound, an acid, and a polar solvent are mixed to carry out a condensation reaction to obtain a 7-acylhydrazone-cyclopentenopyridine compound; 8. The preparation method according to claim 7, characterized in that The molar ratio of the compound 2 to the hydrazide compound is 1:1-3; The acid includes one or more of formic acid, acetic acid, propionic acid, lactic acid and oxalic acid; The polar solvent includes one or more of lower alcohol, water, benzene solvent and amide solvent; The condensation reaction temperature is 0-60° C., and the reaction time is 1-10 hours.

9. A pharmaceutical composition, characterized in that The invention comprises an active component and pharmaceutically acceptable excipients; the active component comprises the 7-acylhydrazone-cyclopentenopyridine compound according to any one of claims 1 to 6.

10. Use of the 7-acylhydrazone-cyclopentapyridine compound according to any one of claims 1 to 6 or the pharmaceutical composition according to claim 9 in the preparation of insecticides, fungicides, herbicides, antiviral drugs, anti-HIV drugs or anticancer drugs.