Synthesis, Antifungal Activity, DFT Study and Molecular Dynamics Simulation of Novel 4‐(1,2,4‐Oxadiazol‐3‐yl)‐<i>N</i>‐(4‐phenoxyphenyl)benzamide Derivatives

Yang, Zihui; Liu, Qingsong; Sun, Yue; Sun, Xuebao; Chen, Linlin; Sun, Lu; Gu, Wen

doi:10.1002/cbdv.202100651

Cited by 8 publications

(5 citation statements)

References 40 publications

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“…Smaller gaps, indicating easier electron transfer, are associated with higher polarizability and enhanced reactivity, while larger gaps signify greater stability and lower reactivity [27]. By studying the properties of the HOMO and LUMO, we can gain valuable information about a molecule's susceptibility to reactions, its capacity for excited-state behavior, and its propensity to interact with other molecules, all of which contribute to understanding its potential biological activity [28]. The calculated energy values for the FMOs (EHOMO, ELUMO) and their energy gaps, as well as the global reactivity descriptors in the absence of a solvent, are mentioned in Table 1.…”

Section: Global Reactivity Indicesmentioning

confidence: 99%

Theoretical Study of Benzothiazole and Its Derivatives: Molecular Structure, Spectroscopic Properties, NBO, MEP and TD-DFT Analyses

Abdoulaye,

Lucie,

Lamoussa

et al. 2024

MSCE

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Benzothiazole (BTH) and its derivatives are organic molecules with biologic actions. Because of their many applications, they are produced on a massive scale and used in a number of environmental compartments. Their discharge into water produces environmental problems, exposing our environment to public health problems. A solution that can contribute to their deterioration is becoming a necessity. For this reason, a conceptual analysis of the reactivity of benzothiazole and four of its compounds was undertaken in order to investigate certain aspects of their biodegradability. A theoretical investigations of the compounds studied were conducted in the gas and water phases with the most widely used density functional theory method, Becke-3-Parameter-Lee-Yang-Parr (B3LYP) with 6-31G+ (d, p) basis. Reactivity study calculated global indices of reactivity revealed that 2-SCH3_BTH is the most reactive. Dipole moment values analysis reveals that 2-NH2_BTH is the most soluble in water, while the lipophilicity shows that 2-NH2_BTH is the most hydrophilic compound. Thermodynamic parameters values reflect that reactions are respectively exothermic and spontaneous. By analyzing an Electrostatic Molecular Potential (EMP) map, researchers can pinpoint reactive sites on a molecule and anticipate its reactivity. This assessment is further enhanced by incorporating global and local reactivity descriptors. Additionally, an exploration of frontier molecular orbitals offers valuable insights into the molecule's charge transfer characteristics. Moreover, a combined examination of internal and external molecular interactions unveils hyperconjugative interactions arising from charge delocalization, as elucidated through natural bond orbital (NBO) analysis.

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Section: Global Reactivity Indicesmentioning

confidence: 99%

Theoretical Study of Benzothiazole and Its Derivatives: Molecular Structure, Spectroscopic Properties, NBO, MEP and TD-DFT Analyses

Abdoulaye,

Lucie,

Lamoussa

et al. 2024

MSCE

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“…14. 70 Based on the fungicide flufenoxadiazam, the intriguing diaryl ether substructure was introduced at the amine's side site. The preliminary in vitro antifungal assay indicated that most of the synthesized compounds exhibited moderate to good fungicidal activity against five plant pathogenic fungi at 20 mg L −1 ( Botrytis cinerea , Rhizoctonia solani , Sclerotinia sclerotiorum , Alternaria solani , and Gibberella zeae ).…”

Section: 24-oxadiazole Derivatives With Pesticidal Activitymentioning

confidence: 99%

1,2,4-Oxadiazole as a potential scaffold in agrochemistry: a review

Zhong,

Wu,

et al. 2023

Org. Biomol. Chem.

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“…Another antifungal application of TFMO containing compounds was reported by Yang et al [22]. The design of active compounds was guided by previous TFMO HDACi and diphenyl ether moieties, frequently used in pesticides.…”

Section: Zbg Scaffoldsmentioning

confidence: 99%

Significance of Five-Membered Heterocycles in Human Histone Deacetylase Inhibitors

2023

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Five-membered heteroaromatic rings, in particular, have gained prominence in medicinal chemistry as they offer enhanced metabolic stability, solubility and bioavailability, crucial factors in developing effective drugs. The unique physicochemical properties and biological effects of five-membered heterocycles have positioned them as key structural motifs in numerous clinically effective drugs. Hence, the exploration of five-ring heterocycles remains an important research area in medicinal chemistry, with the aim of discovering new therapeutic agents for various diseases. This review addresses the incorporation of heteroatoms such as nitrogen, oxygen and sulfur into the aromatic ring of these heterocyclic compounds, enhancing their polarity and facilitating both aromatic stacking interactions and the formation of hydrogen bonds. Histone deacetylases are present in numerous multiprotein complexes within the epigenetic machinery and play a central role in various cellular processes. They have emerged as important targets for cancer, neurodegenerative diseases and other therapeutic indications. In histone deacetylase inhibitors (HDACi’s), five-ring heterocycles perform various functions as a zinc-binding group, a linker or head group, contributing to binding activity and selective recognition. This review focuses on providing an up-to-date overview of the different five-membered heterocycles utilized in HDACi motifs, highlighting their biological properties. It summarizes relevant publications from the past decade, offering insights into the recent advancements in this field of research.

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Synthesis, Antifungal Activity, DFT Study and Molecular Dynamics Simulation of Novel 4‐(1,2,4‐Oxadiazol‐3‐yl)‐N‐(4‐phenoxyphenyl)benzamide Derivatives

Cited by 8 publications

References 40 publications

Theoretical Study of Benzothiazole and Its Derivatives: Molecular Structure, Spectroscopic Properties, NBO, MEP and TD-DFT Analyses

Theoretical Study of Benzothiazole and Its Derivatives: Molecular Structure, Spectroscopic Properties, NBO, MEP and TD-DFT Analyses

1,2,4-Oxadiazole as a potential scaffold in agrochemistry: a review

Significance of Five-Membered Heterocycles in Human Histone Deacetylase Inhibitors

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