Azine Derivatives as a New Generation of Insect Growth Regulators

Eberle, Martin; Farooq, Saleem; Jeanguenat, André; Mousset, Deborah; Steiger, Arthur; Trah, Stephan; Zambach, Werner; Rindlisbacher, Alfred

doi:10.2533/000942903777678560

Cited by 10 publications

(2 citation statements)

References 4 publications

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“…On the other hand, aldazines and ketazines with a conjugated hydrazone system (C=N-N=C) were exploited in various pharmacological studies and many commercial applications. Both symmetric and asymmetric azines have demonstrated biological activities as antimicrobial, antibacterial, anti-inflammatory, antimalarial dyes, anticonvulsant, insect growth regulating, and many other activities [21][22][23][24][25]. Furthermore, several aldazine and ketazine derivatives possessed antiproliferative properties and were applied as cytotoxic agents capable of preventing cell progression in malignant cells via various mechanisms [26][27][28].…”

Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis and Molecular Docking Studies of New Azines Bearing Indole as Anticancer Agents

et al. 2023

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The development of new approaches for the synthesis of new bioactive heterocyclic derivatives is of the utmost importance for pharmaceutical industry. In this regard, the present study reports the green synthesis of new benzaldazine and ketazine derivatives via the condensation of various carbonyl compounds (aldehydes and ketones with the 3-(1-hydrazineylideneethyl)-1H-indole using the grinding method with one drop of acetic acid). Various spectroscopic techniques were used to identify the structures of the synthesized derivatives. Furthermore, the anticancer activities of the reported azine derivatives were evaluated against colon, hepatocellular, and breast carcinoma cell lines using the MTT technique with doxorubicin as a reference medication. The findings suggested that the synthesized derivatives exhibited potential anti-tumor activities toward different cell lines. For example, 3c, 3d, 3h, 9, and 13 exhibited interesting activity with an IC50 value of 4.27–8.15 µM towards the HCT-116 cell line as compared to doxorubicin (IC50 = 5.23 ± 0.29 µM). In addition, 3c, 3d, 3h, 9, 11, and 13 showed excellent cytotoxic activities (IC50 = 4.09–9.05 µM) towards the HePG-2 cell line compared to doxorubicin (IC50 = 4.50 ± 0.20 µM), and 3d, 3h, 9, and 13 demonstrated high potency (IC50 = 6.19–8.39 µM) towards the breast cell line (MCF-7) as compared to the reference drug (IC50 = 4.17 ± 0.20 µM). The molecular interactions between derivatives 3a-h, 7, 9, 11, 13, and the CDK-5 enzyme (PDB ID: 3IG7) were studied further using molecular docking indicating a high level of support for the experimental results. Furthermore, the drug-likeness analysis of the reported derivatives indicated that derivative 9 (binding affinity = −8.34 kcal/mol) would have a better pharmacokinetics, drug-likeness, and oral bioavailability as compared to doxorubicin (−7.04 kcal/mol). These results along with the structure–activity relationship (SAR) of the reported derivatives will pave the way for the design of additional azines bearing indole with potential anticancer activities.

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Section: Introductionmentioning

confidence: 99%

Mechanochemical Synthesis and Molecular Docking Studies of New Azines Bearing Indole as Anticancer Agents

et al. 2023

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“…Ketazines, mixed azines, and cyclic compounds have exhibited antitumor [7][8][9][10][11][12], anti-bacterial [13][14][15][16][17][18][19][20], anti-inflammatory [21], antimalarial dyes [22], anticonvulsant [23,24], insect growth regulators [25] and many other activities. Contrary, acyclic aldazines are much less studied.…”

Section: Introductionmentioning

confidence: 99%