cis-Nitenpyram Analogues Containing 1,4-Dihydropyridine: Synthesis, Insecticidal Activities, and Molecular Docking Studies

被引：11
|
作者：
Sun Chuanwen [1 ]
Chen Yanxia [1 ]
Liu Tianyan [1 ]
Wu Ying [1 ]
Fang Ting [1 ]
Wang Jing [1 ]
Xing Jiahua [2 ]
机构：
[1] Shanghai Normal Univ, Coll Life & Environm Sci, Shanghai 200234, Peoples R China
[2] Branch Natl Pesticide R&D S Ctr, Bioassay Dept, Hangzhou 310023, Zhejiang, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2012年 / 30卷 / 07期
基金：
中国国家自然科学基金;
关键词：
cis-nitenpyram analogue; 1; 4-dihydropyridine; synthesis; insecticidal acvitity; molecular docking; NITROMETHYLENE NEONICOTINOIDS; NICOTINIC RECEPTOR; RESISTANCE; CONFIGURATION; SELECTIVITY; FEATURES;
D O I：
10.1002/cjoc.201200165
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel series of cis-nitenpyram analogues (2a2p) were designed and prepared by introducing the 1,4-dihydropyridine, with their cis-configuration confirmed by X-ray diffraction. Preliminary bioassays showed that most compounds exhibited good insecticidal activities at 20 mg/L against Aphis medicagini, and analogues 2a and 2d afforded the best activity, and both of them had 100% mortality at 4 mg/L. In addition, molecular docking studies were also performed to model the ligand-receptor complexes, and the results explained the structure-activity relationships observed in vitro, which may provide some useful information for future design of new insecticides.
引用
收藏
页码：1415 / 1422
页数：8
相关论文
共 50 条
  • [31] Design, Synthesis, Evaluation and Molecular Docking Studies of Novel Triazole Linked 1,4-Dihydropyridine-isatin Scaffolds as Potent Anticancer Agents
    Deswal, Nidhi
    Shrivastava, Ankita
    Hossain, Md Summon
    Gahlyan, Parveen
    Bawa, Rashim
    Gupta, Rinkoo Devi
    Kumar, Rakesh
    CHEMISTRYSELECT, 2021, 6 (04): : 717 - 725
  • [32] Synthesis of new derivatives containing pyridine, investigation of MAO inhibitory activities and molecular docking studies
    Osmaniye, Derya
    Saglik, Begum Nurpelin
    Levent, Serkan
    Ozkay, Yusuf
    Kaplancikli, Zafer Asim
    Turan, Gulhan
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, 2022, 77 (11-12): : 509 - 517
  • [33] Discovery of new symmetrical and asymmetrical nitrile-containing 1,4-dihydropyridine derivatives as dual kinases and P-glycoprotein inhibitors: synthesis, in vitro assays, and in silico studies
    Saad, Mohamed H.
    El-Moselhy, Tarek F.
    Nabaweya, S. El-Din
    Mehany, Ahmed B. M.
    Belal, Amany
    Abourehab, Mohammed A. S.
    Tawfik, Haytham O.
    El-Hamamsy, Mervat H.
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2022, 37 (01) : 2489 - 2511
  • [34] Green synthesis, molecular docking and anticancer activity of novel 1,4-dihydropyridine-3,5-Dicarbohydrazones under grind-stone chemistry
    Gomha, Sobhi M.
    Muhammad, Zeinab A.
    Abdel-aziz, Hassan M.
    Matar, Islam K.
    El-Sayed, Abdelaziz A.
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2020, 13 (01) : 6 - 17
  • [35] Design, Synthesis, Molecular docking, and Antibacterial Study of Aminomethyl Triazolo Substituted Analogues of Benzimidazolo [1,4]-benzodiazepine
    Devi, Meenu
    Jaiswal, Shivangi
    Yaduvanshi, Neetu
    Jain, Sonika
    Jain, Smita
    Verma, Kanika
    Verma, Rahul
    Kishore, Dharma
    Dwivedi, Jaya
    Sharma, Swapnil
    JOURNAL OF MOLECULAR STRUCTURE, 2023, 1286
  • [36] Synthesis, molecular docking, DFT study, and in vitro antimicrobial activity of some 4-(biphenyl-4-yl)-1,4-dihydropyridine and 4-(biphenyl-4-yl)pyridine derivatives
    Malani, Alimamad
    Makwana, Atul
    Monapara, Jahnvi
    Ahmad, Iqrar
    Patel, Harun
    Desai, Nisheeth
    JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY, 2021, 35 (11)
  • [37] Chiral 1,5-disubstituted 1,3,5-hexahydrotriazine-2-N-nitroimine analogues as novel potent neonicotinoids: Synthesis, insecticidal evaluation and molecular docking studies
    Sun, Chuanwen
    Zhu, Jun
    Wang, Haifeng
    Jin, Jia
    Xing, Jiahua
    Yang, Dingrong
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) : 11 - 20
  • [38] New 1,2,3-Benzotriazole-based thiourea analogues: Synthesis, alpha-glucosidase, urease activities and molecular docking study
    Khan, Urooba
    Hayat, Shawkat
    Nabi, Muhammad
    Ullah, Hayat
    Umar, Ali
    Khan, Muhammad Saleem
    Rahim, Fazal
    Khan, Muhammad Azam
    Iqbal, Rashid
    Gul, Farzana
    Perviaz, Muhammed
    CHEMICAL DATA COLLECTIONS, 2025, 56
  • [39] 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
  • [40] Synthesis, anti-diabetic evaluation and molecular docking studies of 4-(1-aryl-1H-1, 2, 3-triazol-4-yl)-1,4-dihydropyridine derivatives as novel 11-β hydroxysteroid dehydrogenase-1 (11β-HSD1) inhibitors
    Praveenkumar, E.
    Gurrapu, Nirmala
    Kolluri, Prashanth Kumar
    Yerragunta, Vishwanadham
    Kunduru, Bharathi Reddy
    Subhashini, N. J. P.
    BIOORGANIC CHEMISTRY, 2019, 90
12345