Design, Synthesis, and Insecticidal Activity Evaluation of Piperine Derivatives

Overview

Journal Front Chem

Specialty Chemistry

Date 2022 Aug 12

PMID 35958231

Authors

Chiying Zhang

Qingqiang Tian

Yahui Li

Affiliations

Soon will be listed here.

Abstract

Structural optimization of natural products has become one of the most effective ways to develop novel pesticides. In this study, 30 novel pesticide derivatives containing a linear bisamide were synthesized. Then, their insecticidal activities against were evaluated. Results indicate that different bisamide substitutes show different larvicidal structure-activity relationships. At the same time, 2-trifluoroethyl is the most efficient substituent. The bioactivity results showed that most of the desired compounds exhibited better insecticidal activity against than piperine. Among them, resulted in 90% mortality at 1 mg/ml concentration. This study provides a novel protocol for the discovery of new insecticides. The molecular docking results indicated that compound D28 could act on -aminobutyric acid receptors.

Citing Articles

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Han J, Zhang S, He J, Li T Toxins (Basel). 2023; 15(12).

PMID: 38133200 PMC: 10747706. DOI: 10.3390/toxins15120696.

Cantharidin-Based Verbenone Derivatives as a Novel Insecticide against : Design, Synthesis, Insecticidal Activity Evaluation, and 3D QSAR Study.

Lee K, Nada H, Kim M, Park H, Lee K, Seo D Biomolecules. 2023; 13(8).

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References

Wang H, Yang Z, Fan Z, Wu Q, Zhang Y, Mi N . Synthesis and insecticidal activity of N-tert-butyl-N,N'-diacylhydrazines containing 1,2,3-thiadiazoles. J Agric Food Chem. 2010; 59(2):628-34. DOI: 10.1021/jf104004q. View

Franklim T, Freire-de-Lima L, de Nazareth Sa Diniz J, Previato J, Castro R, Mendonca-Previato L . Design, synthesis and trypanocidal evaluation of novel 1,2,4-triazoles-3-thiones derived from natural piperine. Molecules. 2013; 18(6):6366-82. PMC: 6270562. DOI: 10.3390/molecules18066366. View

Sun J, Lv X, Qiu H, Wang Y, Du Q, Li D . Synthesis, biological evaluation and molecular docking studies of pyrazole derivatives coupling with a thiourea moiety as novel CDKs inhibitors. Eur J Med Chem. 2013; 68:1-9. DOI: 10.1016/j.ejmech.2013.07.003. View

Gaur R, Bao G . Chemistry and Pharmacology of Natural Catechins from Camellia sinensis as Anti-MRSA Agents. Curr Top Med Chem. 2021; 21(17):1519-1537. DOI: 10.2174/1568026621666210524100632. View

Xia D, Liu H, Cheng X, Maraswami M, Chen Y, Lv X . Recent Developments of Coumarin-based Hybrids in Drug Discovery. Curr Top Med Chem. 2022; 22(4):269-283. DOI: 10.2174/1568026622666220105105450. View

Shen J, Li D, Zhang S, Zhu X, Wan H, Li J . Fitness and inheritance of metaflumizone resistance in Plutella xylostella. Pestic Biochem Physiol. 2017; 139:53-59. DOI: 10.1016/j.pestbp.2017.04.010. View

Sun Y, Jiang Y, Wu H, Xu N, Ma Z, Zhang C . Function of four mitochondrial genes in fumigation lethal mechanisms of Allyl Isothiocyanate against Sitophilus zeamais adults. Pestic Biochem Physiol. 2021; 179:104947. DOI: 10.1016/j.pestbp.2021.104947. View

Han Q, Wu N, Li H, Zhang J, Li X, Deng M . A Piperine-Based Scaffold as a Novel Starting Point to Develop Inhibitors against the Potent Molecular Target ChtI. J Agric Food Chem. 2021; 69(27):7534-7544. DOI: 10.1021/acs.jafc.0c08119. View

Kimura K, Yamaoka M, Kamisaka Y . Inhibition of lipid accumulation and lipid body formation in oleaginous yeast by effective components in spices, carvacrol, eugenol, thymol, and piperine. J Agric Food Chem. 2009; 54(10):3528-34. DOI: 10.1021/jf0531149. View

10.

Tang M, Wang Z, Shi Y . Involvement of cytochrome c release and caspase activation in toosendanin-induced PC12 cell apoptosis. Toxicology. 2004; 201(1-3):31-8. DOI: 10.1016/j.tox.2004.03.023. View

11.

Chen Y, Wu J, Wang A, Qi Z, Jiang T, Chen C . Discovery of N-(5-((5-chloro-4-((2-(isopropylsulfonyl)phenyl)amino)pyrimidin-2-yl)amino)-4-methoxy-2-(4-methyl-1,4-diazepan-1-yl)phenyl)acrylamide (CHMFL-ALK/EGFR-050) as a potent ALK/EGFR dual kinase inhibitor capable of overcoming a variety of.... Eur J Med Chem. 2017; 139:674-697. DOI: 10.1016/j.ejmech.2017.08.035. View

12.

Santana Ribeiro T, Freire-de-Lima L, Previato J, Mendonca-Previato L, Heise N, de Lima M . Toxic effects of natural piperine and its derivatives on epimastigotes and amastigotes of Trypanosoma cruzi. Bioorg Med Chem Lett. 2004; 14(13):3555-8. DOI: 10.1016/j.bmcl.2004.04.019. View

13.

Liu Z, Li Q, Song B . Recent Research Progress in and Perspectives of Mesoionic Insecticides: Nicotinic Acetylcholine Receptor Inhibitors. J Agric Food Chem. 2020; 68(40):11039-11053. DOI: 10.1021/acs.jafc.0c02376. View

14.

Seeliger D, de Groot B . Ligand docking and binding site analysis with PyMOL and Autodock/Vina. J Comput Aided Mol Des. 2010; 24(5):417-22. PMC: 2881210. DOI: 10.1007/s10822-010-9352-6. View

15.

Tang J, Lv X, Wang X, Sun J, Zhang Y, Yang Y . Design, synthesis, biological evaluation and molecular modeling of novel 1,3,4-oxadiazole derivatives based on Vanillic acid as potential immunosuppressive agents. Bioorg Med Chem. 2012; 20(14):4226-36. DOI: 10.1016/j.bmc.2012.05.055. View

16.

Lima Neto J, da Solidade Ribeiro L, de Siqueira H . Inheritance and Fitness of Plutella xylostella (Lepidoptera: Plutellidae) Resistance to Chlorfenapyr. J Econ Entomol. 2021; 114(2):875-884. DOI: 10.1093/jee/toaa299. View

17.

Wu W, Wang M, Zhu J, Zhou W, Hu Z, Ji Z . Five new insecticidal sesquiterpenoids from Celastrus angulatus. J Nat Prod. 2001; 64(3):364-7. DOI: 10.1021/np0004193. View

18.

Tong Z, Duan J, Wu Y, Liu Q, He Q, Shi Y . Evaluation of Highly Detectable Pesticides Sprayed in L.: Degradation Behavior and Risk Assessment for Honeybees. Molecules. 2018; 23(10). PMC: 6222740. DOI: 10.3390/molecules23102482. View

19.

Liu H, Ren Z, Wang W, Gong J, Chu M, Ma Q . Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity. Eur J Med Chem. 2018; 157:81-87. DOI: 10.1016/j.ejmech.2018.07.059. View

20.

Zhao Z, Xu Q, Chen W, Wang S, Yang Q, Dong Y . Rational Design, Synthesis, and Biological Investigations of -Methylcarbamoylguanidinyl Azamacrolides as a Novel Chitinase Inhibitor. J Agric Food Chem. 2022; 70(16):4889-4898. DOI: 10.1021/acs.jafc.2c00016. View