NOVEL NITENPYRAM ANALOGUES WITH TETRAHYDROPYRIDONE-FIXED CIS-CONFIGURATION: SYNTHESIS, INSECTICIDAL ACTIVITIES, AND MOLECULAR DOCKING STUDIES

被引：5
作者：
Sun, Chuan-Wen [1 ]
Wang, Jing [1 ]
Wu, Ying [1 ]
Nan, Shi-Bin [1 ]
Zhang, Wang-Geng
机构：
[1] Shanghai Normal Univ, Coll Life & Environm Sci, Shanghai 200234, Peoples R China
来源：
HETEROCYCLES | 2013年 / 87卷 / 09期
基金：
中国国家自然科学基金;
关键词：
Nitenpyram Analogue; Synthesis; Insecticidal Acvitity; cis-Configuration; Molecular Docking; NITROMETHYLENE NEONICOTINOIDS; CROSS-RESISTANCE; MELDRUMS ACID; DIVERSITY; MECHANISMS; MOTH;
D O I：
10.3987/COM-13-12766
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
To make further researches on the diversity of nitenpyram analogues with a cis-nitromethylene configuration, a series of cis-nitenpyram analogues (3a-q) with tetrahydropyridone-fixed cis-configuration were designed and synthesized. Preliminary bioassays showed that most of the designed nitenpyram analogues exhibited good insecticidal activity at 100 mg/L against Nilaparvata lugens and Myzus persicae, while analogues 3n afforded the best in vitro activity. Modeling the ligand-receptor complexes by molecular docking study revealed the analogues 3 with various substituents on phenyl show their different binding affinities to the insect nAChR, which also explained the structure-activity relationships observed in vitro.
引用
收藏
页码：1865 / 1880
页数：16
相关论文
共 50 条
  • [31] Synthesis, Molecular docking, Antioxidant, Anti-TB, and Potent MCF-7 Anticancer Studies of Novel Aryl-carbohydrazide Analogues
    Thorat, Bapu R.
    Mali, Suraj N.
    Wagh, Rahul R.
    Yamgar, Ramesh S.
    CURRENT COMPUTER-AIDED DRUG DESIGN, 2022, 18 (04) : 247 - 257
  • [32] Synthesis, quantum mechanical calculations, antimicrobial activities and molecular docking studies of five novel 2,5-disubstituted benzoxazole derivatives
    Temiz-Arpaci, Ozlem
    Zeyrek, Celal Tugrul
    Arisoy, Mustafa
    Erol, Meryem
    Celik, Ismail
    Kaynak-Onurdag, Fatma
    JOURNAL OF MOLECULAR STRUCTURE, 2021, 1245
  • [33] Synthesis, Biological Activities, Antioxidant Properties, and Molecular Docking Studies of Novel Bis-Schiff Base Podands as Responsive Chemosensors for Anions
    Yapar, Gonul
    Demir, Neslihan
    Kiraz, Askin
    Ozkat, Gozde Yalcin
    Yildiz, Mustafa
    JOURNAL OF MOLECULAR STRUCTURE, 2022, 1266
  • [34] 1,2,4-Triazole and 1,3,4-oxadiazole analogues: Synthesis, MO studies, in silico molecular docking studies, antimalarial as DHFR inhibitor and antimicrobial activities
    Thakkar, Sampark S.
    Thakor, Parth
    Doshi, Hiren
    Ray, Arabinda
    BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (15) : 4064 - 4075
  • [35] Synthesis, biological activities, and molecular docking studies of triazolo[4,3-b]triazine derivatives as a novel class of α-glucosidase and α-amylase inhibitors
    Seyfi, Soheila
    Salarinejad, Somayeh
    Moghimi, Setareh
    Toolabi, Mahsa
    Sadeghian, Nastaran
    Tuezuen, Burak
    Firoozpour, Loghman
    Ketabforoosh, Shima H. M. E.
    Taslimi, Parham
    Foroumadi, Alireza
    ARCHIV DER PHARMAZIE, 2024, 357 (07)
  • [36] Synthesis, characterization, biological evaluation, ADMET, and molecular docking studies of novel chalcone-sulfonate hybrid compounds as potential antioxidant and antiobesity activities
    Korkmaz, Adem
    Bursal, Ercan
    JOURNAL OF MOLECULAR STRUCTURE, 2025, 1332
  • [37] Synthesis, characterization and biological activities of two novel orthopalladated complexes: Interactions with DNA and bovine serum albumin, antitumour activity and molecular docking studies
    Karami, Kazem
    Hashemi, Sara
    Lipkowski, Janusz
    Mardani, Fatemeh
    Momtazi-borojeni, Amir Abbas
    Lighvan, Zohreh Mehri
    APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (10)
  • [38] Novel 1H-pyrrolo[2,3-b]pyridine sulfonamide analogues: Design, synthesis, in-vitro anticancer and molecular docking studies
    Mothe, Thirupathi
    Konkala, Veera Swamy
    Gopala, Sridhar Goud
    Lingala, Arun Kumar
    Murahari, Kiran Kumar
    Desireddi, Janardana Reddi
    Manchal, Ravinder
    JOURNAL OF MOLECULAR STRUCTURE, 2025, 1322
  • [39] Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies
    Celik, Gonca
    Tatar Yilmaz, Gizem
    Sahin, Huseyin
    Barut, Burak
    Yayli, Nurettin
    TURKISH JOURNAL OF CHEMISTRY, 2023, 47 (01) : 171 - +
  • [40] Design, synthesis, antimycobacterial activity and molecular docking studies of novel 3-(N-substituted glycinamido) benzoic acid analogues as anti tubercular agents
    Veeravarapu, Hymavathi
    Tirumalasetty, Mohan
    Kurati, SonyPriya
    Wunnava, Umarani
    Muthyala, Murali Krishna Kumar
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2020, 30 (23)
12345