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

页码：1415 / 1422

页数：8

共 50 条

[31] Discovery of bis-aromatic ring neonicotinoid analogues fixed as cis-configuration: Synthesis, insecticidal activities, and molecular docking studies
Sun, Chuanwen
Jin, Jia
Zhu, Jun
Wang, Haifeng
Yang, Dingrong
Xing, Jiahua
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (11) : 3301 - 3305
[32] Docking and QSAR Studies of 1,4-Dihydropyridine Derivatives as Anti-Cancer Agent
Mollazadeh, Shirin
Shamsara, Jamal
Iman, Maryam
Hadizadeh, Farzin
RECENT PATENTS ON ANTI-CANCER DRUG DISCOVERY, 2017, 12 (02) : 174 - 185
[33] Synthesis and structural conformation studies of a potent unsymmetrical 1,4-dihydropyridine
Naveen, S.
Anandalwar, Sridhar M.
Prasad, J. Shashidhara
Manvar, Dinesh
Mishra, Arun
Shah, Anamik
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2008, 38 (04) : 315 - 319
[34] Synthesis and Structural Conformation Studies of a Potent Unsymmetrical 1,4-Dihydropyridine
S. Naveen
Sridhar M. Anandalwar
J. Shashidhara Prasad
Dinesh Manvar
Arun Mishra
Anamik Shah
Journal of Chemical Crystallography, 2008, 38 : 315 - 319
[35] Design, Multicomponent Synthesis, and Bioactivities of Novel Neonicotinoid Analogues with 1,4-Dihydropyridine Scaffold
Zhang, Wenwen
Yang, Xiaobao
Chen, Weidong
Xu, Xiaoyong
Li, Lu
Zhai, Hongbin
Li, Zhong
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (05) : 2741 - 2745
[36] Phenylboronic acid catalyzed synthesis of polysubstituted 1,4-dihydropyridine derivatives as promising antioxidant agents correlated with molecular docking
Pansuriya, Ketan
Lalpara, Jaydeep N.
Hadiyal, Sanjay D.
Dhaduk, Bhavin B.
Dubal, G. G.
CHEMICAL DATA COLLECTIONS, 2022, 42
[37] Synthesis, inhibition effects, molecular docking and theoretical studies as Paraoxonase 1 (PON1) inhibitors of novel 1,4-dihydropyridine substituted sulfonamide derivatives
Kaya, Mustafa Oguzhan
Demirci, Tuna
Ozdemir, Oguzhan
Calisir, Umit
Sonmez, Fatih
Arslan, Mustafa
MEDICINAL CHEMISTRY RESEARCH, 2023, 32 (05) : 841 - 855
[38] Synthesis, inhibition effects, molecular docking and theoretical studies as Paraoxonase 1 (PON1) inhibitors of novel 1,4-dihydropyridine substituted sulfonamide derivatives
Mustafa Oguzhan Kaya
Tuna Demirci
Oguzhan Ozdemir
Umit Calisir
Fatih Sonmez
Mustafa Arslan
Medicinal Chemistry Research, 2023, 32 : 841 - 855
[39] Synthesis and evaluation of calcium channel antagonist activity of some new imidazolyl 1,4-dihydropyridine analogues containing carbamoyl substitute
Javidnia, Katayoun
Miri, Ramin
Edraki, Najme
Khoshneviszadeh, Mehdi
ACTA PHARMACOLOGICA SINICA, 2006, 27 : 130 - 130
[40] SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITIES OF NEW 1,4-DIHYDROPYRIDINE DERIVATIVES CONTAINING A NITROOXY MOIETY AT THE 3-ESTER POSITION
OGAWA, T
NAKAZATO, A
TSUCHIDA, K
HATAYAMA, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1993, 41 (01) : 108 - 116

← 1 2 3 4 5 →