Bridged heterocyclic neonicotinoid analogues: design, synthesis, and insecticidal activity

Chen, Nanyang; Xia, Shanshan; Zou, Minming; Shao, Xusheng

doi:10.1007/s11164-014-1631-8

Cited by 8 publications

(11 citation statements)

References 22 publications

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“…Several methods are reported for the synthesis of heterocylic [3.3.3]propellanes. Oxa-aza [3.3.3]propellanes were synthesized by Alizadeh et al [4,[22][23][24], Yavari et al [25], Chen et al [26] and Zhang et al [27]. Hassan et al reported the formation of oxaaza-and bisoxathia-aza [3.3.3]-propellanes via nucleophilic addition of symmetrical and unsymmetrical N 1 ,N 2 -disubstituted-1,2-dicarbothioamides on dicyanomethylene-1,3-indanedione 1 [28].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

Hassan

Aly

Mohamed

et al. 2019

Bioorganic Chemistry

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A large number of natural products containing the propellane scaffold have been reported to exhibit cytotoxicity against several cancers; however, their mechanism of action is still unknown. Anticancer drugs targeting DNA are mainly composed of small planar molecule/s that can interact with the DNA helix, causing DNA malfunction and cell death. The aim of this study was to design and synthesize propellane derivatives that can act as DNA intercalators and/or groove binders. The unique structure of the propellane derivatives and their ability to display planar ligands with numerous possible geometries, renders them potential starting points to design new drugs targeting DNA in cancer cells. New substituted furo-imidazo[3.3.3]propellanes were synthesized via the reaction of substituted alkenylidene-hydrazinecarbothioamides with 2-(1,3-dioxo-2,3dihydro-1H-2-ylidene) propanedinitrile in tetrahydrofuran at room temperature. The structures of the products were confirmed by a combination of elemental analysis, NMR, ESI-MS, IR and single crystal X-ray analysis. Interestingly, 5c, 5d and 5f showed an ability to interact with Calf Thymus DNA (CT-DNA). Their DNA-binding mode was investigated using a combination of absorption spectroscopy, DNA melting, viscosity, CD spectroscopy measurements, as well as competitive binding studies with several dyes. Their cytotoxicity was evaluated against the NCI-60 panel of cancer cell lines. 5c, 5d and 5f exhibited similar anti-proliferative activity against the A549 non-small cell lung cancer (NSCLC) cell line. Further mechanistic studies revealed their ability to induce DNA damage in the A549 cell line, as well as apoptosis, evidenced by elevated *

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Section: Introductionmentioning

confidence: 99%

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

Hassan

Aly

Mohamed

et al. 2019

Bioorganic Chemistry

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“…The development of neonicotinoids is provoked by the rapid resistance growing [7] and serious bee toxicity [8][9][10]. Thus, there is an urgent need for the development of novel, effective, neonicotinoid replacements.…”

Section: Introductionmentioning

confidence: 99%

PLS Structure-Insecticidal Activity Relationships of Nitromethylene, Pyrrole- and Dihydropyrrole-Fused Neonicotinoids

Borota

Crisan

Bora

et al. 2019

The 23rd International Electronic Conference on Synthetic Organic Chemistry

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A single Neonicotinoids are considered to be one of the important classes of insecticides used at the present time. In this study the partial least squares (PLS) approach is applied to a series of nitromethylene, pyrrole- and dihydropyrrole-fused neonicotinoids to model their insecticidal activity (pLC50 values) against the cowpea aphids. The structures were modeled using the MMFF94s force field. A robust PLS model (3PCs, R2X(Cum) = 0.963, R2Y(cum) = 0.870 and Q2(Cum) = 0.796) with predictive power (CCCext = 0.873, r2m = 0.680, Q2F1 = 0.805, Q2F2 = 0.802, Q2F3 = 0.704) is obtained. New insecticides active against the cowpea aphids can be predicted.

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“…Neonicotinoids are synthetic insecticides acting on the insect nicotinic acetylcholine receptor (nAChR) and have been increasingly used to control various insects during recent decades, especially since imidacloprid was introduced to the market [3]. However, the neonicotinoids success is being provoked by the rapid development of resistance [2] and severe bee toxicity [4][5][6]. It is considered that neonicotinoid insecticides represent the most effective chemical class for the control of sucking insect pests (aphids, whiteflies, leaf-and planthoppers, thrips), micro lepidoptera, and a number of coleopteran pest species [7].…”

Section: Introductionmentioning

confidence: 99%

Insecticidal Activity Evaluation of Phenylazo and Dihydropyrrole-Fused Neonicotinoids Against Cowpea Aphids Using the MLR Approach

Funar-Timofei¹,

Bora²

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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This paper presents a Quantitative Structure-Activity Relationship (QSAR) study of a series of 24 dihydropyrrole-fused and phenylazo neonicotinoid derivatives, with insecticidal activity tested against Cowpea aphids (Aphis craccivora). In this regard, the conformational search ability of the OMEGA software was employed to model neonicotinoid conformer ensembles, using molecular mechanics calculations based on the 94s variant of the Merck Molecular force field (MMFF94). The minimum energy conformers were used to calculate structural descriptors, which were further related to the insecticidal activity (pLC50 values), using the multiple linear regression (MLR) approach. The genetic algorithm was used for variable selection and several criteria for internal and external model validation. A robust model (r2 = 0.880, r2adj = 0.855, q2LOO = 0.827, s = 0.2098, F = 34.295) with predictive power (concordance correlation coefficient (CCC)ext = 0.945, r2m= 0.824) was obtained, using the QSARINS software. The developed model can be confidently used for the prediction of the insecticidal activity of new chemicals, saving a substantial amount of time and money.

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Bridged heterocyclic neonicotinoid analogues: design, synthesis, and insecticidal activity

Cited by 8 publications

References 22 publications

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

Design, synthesis, and DNA interaction studies of furo-imidazo[3.3.3]propellane derivatives: Potential anticancer agents

PLS Structure-Insecticidal Activity Relationships of Nitromethylene, Pyrrole- and Dihydropyrrole-Fused Neonicotinoids

Insecticidal Activity Evaluation of Phenylazo and Dihydropyrrole-Fused Neonicotinoids Against Cowpea Aphids Using the MLR Approach

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