Synthesis, Compound, Emulsification, and Antibacterial Activity of Modified 1,2,4-Trizaole Derivatives

Guo, Haoquan; Dong, Yuguo; Zhu, S. H.; Que, Han; Lu, Xinyu; Zhu, Xiaojun; Cheng, Kanghua; Gu, Xiaoli

doi:10.1021/acsomega.9b00691

Cited by 5 publications

(3 citation statements)

References 5 publications

(10 reference statements)

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“…18 For the triazole fungicide tebuconazole, nevertheless, the presence of the bulky tert-butyl group makes the asymmetric synthesis of its enantiomers by chemical methods a significant challenge. 19 To our current knowledge, the optical purity of tebuconazole enantiomers can only be obtained via chiral high-performance liquid chromatography (HPLC) resolution 20 (Scheme 2). This chiral HPLC resolution approach, however, has inherent limitations in terms of high cost and low efficiency for industrial production.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Chang et al reported the chemical synthesis of ( S )-flutriafol (98% ee ) from its epoxy-precursor ( S )-2,2-disubstituted oxirane, which was asymmetric synthesized through the application of a noble metal rhodium(I)-chiral diene catalyst . For the triazole fungicide tebuconazole, nevertheless, the presence of the bulky tert -butyl group makes the asymmetric synthesis of its enantiomers by chemical methods a significant challenge . To our current knowledge, the optical purity of tebuconazole enantiomers can only be obtained via chiral high-performance liquid chromatography (HPLC) resolution (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

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Chemoenzymatic Asymmetric Synthesis of Chiral Triazole Fungicide (R)-Tebuconazole in High Optical Purity Mediated by an Epoxide Hydrolase from Rhodotorula paludigensis

Hu,

Jia,

et al. 2024

J. Agric. Food Chem.

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Tebuconazole is a chiral triazole fungicide used globally in agriculture as a racemic mixture, but its enantiomers exhibit significant enantioselective dissimilarities in bioactivity and environmental behaviors. The steric hindrance caused by the tertbutyl group makes it a great challenge to synthesize tebuconazole enantiomers. Here, we designed a simple chemoenzymatic approach for the asymmetric synthesis of (R)-tebuconazole, which includes the biocatalytic resolution of racemic epoxy-precursor (2-tert-butyl-2-[2-(4-chlorophenyl)ethyl] oxirane, rac-1a) by Escherichia coli/Rpeh whole cells expressed epoxide hydrolase from Rhodotorula paludigensis (RpEH), followed by a one-step chemocatalytic synthesis of (R)-tebuconazole. It was observed that (S)-1a was preferentially hydrolyzed by E. coli/Rpeh, whereas (R)-1a was retained with a specific activity of 103.8 U/g wet cells and a moderate enantiomeric ratio (E value) of 13.4, which was remarkably improved to 43.8 after optimizing the reaction conditions. Additionally, a gram-scale resolution of 200 mM rac-1a was performed using 150 mg/mL E. coli/Rpeh wet cells, resulting in the retention of (R)-1a in a 97.0% ee s , a 42.5% yield s , and a 40.5 g/L/d space-time yield. Subsequently, the synthesis of highly optical purity (R)-tebuconazole (>99% ee) was easily achieved through the chemocatalytic ring-opening of the epoxy-precursor (R)-1a with 1,2,4-triazole. To elucidate insight into the enantioselectivity, molecular docking simulations revealed that the unique L-shaped substrate-binding pocket of RpEH plays a crucial role in the enantioselective recognition of bulky 2,2-disubstituted oxirane 1a.

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Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Asymmetric Synthesis of Chiral Triazole Fungicide (R)-Tebuconazole in High Optical Purity Mediated by an Epoxide Hydrolase from Rhodotorula paludigensis

Hu,

Jia,

et al. 2024

J. Agric. Food Chem.

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“…Triazoles are five-membered heterocyclic compounds composed of two carbon atoms and three nitrogen atoms. Many nitrogen-rich triazole derivatives can act as weak Lewis bases and are found to be biologically active species. − They are considered pharmacophores capable of interacting with specific biological targets, which are widely used as antitumor, − antibacterial, antifungal, and prebiotic agents . Several commercial drugs with triazole cores have been demonstrated.…”

Section: Introductionmentioning

confidence: 99%

Triazole-Bridged Zinc Dinuclear Complexes: Mechanochemical Synthesis, Crystal Structure, and Biological Activity

et al. 2022

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Two zinc (Zn) complexes, [Zn2(DAT)2Cl4] (I) and [Zn2(DAT)2(NO3)4] (II), were prepared by grinding 3,5-diamino-1,2,4-triazole (C2H5N5, DAT) with Zn precursors such as ZnCl2 and Zn(NO3)2, respectively. This solid-state reaction gives the corresponding Zn complex as the sole product in over 99% yield. This mechanochemical method promotes the selective formation of Zn complexes different from those obtained using the conventional solution-based route. The crystal structures of the two complexes were analyzed by single-crystal X-ray diffraction. Complex (I) crystallizes in the monoclinic space group P21/c, whereas complex (II) crystallizes in the triclinic space group P 1̅. Each complex is characterized by the presence of a characteristic DAT-bridged dimer with one DAT ligand per Zn atom, and the DAT ligand provides a bridge between the two Zn metals. All Zn centers of (I) and (II) adopted a slightly distorted tetrahedral geometry. Both complexes contain a hexanuclear Zn2N4 ring, but their ring structures are different. Complex (I) possesses a boat geometry, while complex (II) has a nearly planar structure. The Zn-bound chlorides of complex (I) form intermolecular N–H···Cl hydrogen bonds that link neighboring molecules. In complex (II), the O atoms in the nitrate groups are hydrogen-bonded to the DAT ligand via O···H–N linkages. Both complexes exhibit blue emissions in the solid state at ambient temperature. They were evaluated as anticancer agents in HeLa, NCCIT, and MCF-7 cancer cell lines, exhibiting promising anticancer activities.

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Green aqueous synthesis and antimicrobial evaluation of 3,5-disubstituted 1,2,4-triazoles

Beyzaei

Malekraisi

Aryan

et al. 2020

Chem Heterocycl Comp

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Synthesis, Compound, Emulsification, and Antibacterial Activity of Modified 1,2,4-Trizaole Derivatives

Cited by 5 publications

References 5 publications

Chemoenzymatic Asymmetric Synthesis of Chiral Triazole Fungicide (R)-Tebuconazole in High Optical Purity Mediated by an Epoxide Hydrolase from Rhodotorula paludigensis

Chemoenzymatic Asymmetric Synthesis of Chiral Triazole Fungicide (R)-Tebuconazole in High Optical Purity Mediated by an Epoxide Hydrolase from Rhodotorula paludigensis

Triazole-Bridged Zinc Dinuclear Complexes: Mechanochemical Synthesis, Crystal Structure, and Biological Activity

Green aqueous synthesis and antimicrobial evaluation of 3,5-disubstituted 1,2,4-triazoles

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