Dipole moment in medicinal research: Green and sustainable approach

Das, Aparna; Banik, Bimal K.

doi:10.1016/b978-0-12-817592-7.00021-6

Cited by 17 publications

(11 citation statements)

References 152 publications

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“…The most relevant synthetic pathways for N-based and O-based heterocyclic compounds mediated by laccases are listed in Table 1 , which summarize also the optimized reaction conditions and obtained yields. Most of these heterocyclic aromatic compounds are important active pharmaceutical ingredients, associated to a wide range of biological and pharmacological activities such as anti-tumour, anti-fungal, antiviral, anti-allergic, antidepressant, antioxidant, anti-HIV, anticonvulsant, anti-diabetic, antipsychotic, anti-malarian and anti-inflammatory activities [ 10 , 22 , 72 , 73 , 74 , 75 , 76 , 77 ].…”

Section: Application Of Laccases In Bio-oxidative Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

“…Phenothiazines are heterocyclic sulphur compounds applicable in many areas of medicine, in particular in the treatment of neurodegenerative diseases such as Alzheimer’s and Parkinson’s diseases [ 74 ]. Considering that laccases can oxidize hydroquinones and catechols to produce in situ p - and o -quinones, the cross-coupling reactions involving sulphur-based nucleophiles (1,2-ethanedithiol or 2-aminothiophenol) were exploited providing a sustainable approach for the synthesis of 2,3-ethylenedithio1,4-quinone and phenothiazine substructures ( Scheme 16 A) [ 97 , 109 ].…”

Section: Application Of Laccases In Bio-oxidative Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

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Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores

2021

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Laccases are multicopper oxidases that have shown a great potential in various biotechnological and green chemistry processes mainly due to their high relative non-specific oxidation of phenols, arylamines and some inorganic metals, and their high redox potentials that can span from 500 to 800 mV vs. SHE. Other advantages of laccases include the use of readily available oxygen as a second substrate, the formation of water as a side-product and no requirement for cofactors. Importantly, addition of low-molecular-weight redox mediators that act as electron shuttles, promoting the oxidation of complex bulky substrates and/or of higher redox potential than the enzymes themselves, can further expand their substrate scope, in the so-called laccase-mediated systems (LMS). Laccase bioprocesses can be designed for efficiency at both acidic and basic conditions since it is known that fungal and bacterial laccases exhibit distinct optimal pH values for the similar phenolic and aromatic amines. This review covers studies on the synthesis of five- and six-membered ring heterocyclic cores, such as benzimidazoles, benzofurans, benzothiazoles, quinazoline and quinazolinone, phenazine, phenoxazine, phenoxazinone and phenothiazine derivatives. The enzymes used and the reaction protocols are briefly outlined, and the mechanistic pathways described.

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Section: Application Of Laccases In Bio-oxidative Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

Section: Application Of Laccases In Bio-oxidative Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores

2021

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“…Hydrazide structures have been determined to exhibit a wide range of biological and pharmaceutical activities and have been successfully used to discover lead compounds. 14 In terms of agricultural fungicidal activity, for example, Wang's group reported benzoic hydrazides (1) containing a 1,2,3-triazole group as potential SDH inhibitors, 15 Yang and co-workers synthesized pyrazole hydrazides (2) bearing a 1,3,4-oxadiazole core as agrochemicals against plant fungus 16 and Ye's group prepared 1,2,3-triazole hydrazide derivatives (3) exhibiting anti-phytopathogenic activity. 17 structures controlling agricultural pathogens, 18−20 such as compounds 4−6 listed in Figure 2.…”

Section: Introductionmentioning

confidence: 99%

Discovery of Aryloxy-, Arylthio-, and Arylamino-Containing Acethydrazides as Fungicidal Agents

Fang

Chen

Liu

et al. 2022

J. Agric. Food Chem.

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The development of new green fungicides is an effective way to solve the resistance of agricultural pathogens and plays an important role in promoting high-quality and sustainable development of modern agriculture. In this project, a series of aryloxy-, arylthio-, and arylamino-containing acethydrazide derivatives were designed, synthesized, and characterized by 1 H nuclear magnetic resonance (NMR), 13 C NMR, and high-resolution mass spectrometry (HRMS). The fungicidal bioassays indicated that some compounds showed excellent and broad-spectrum fungicidal activity, and the structure−activity relationship was discussed. The in vivo fungicidal activity demonstrated that compounds C4 and D8 exhibited good preventative effects against Fusarium graminearum infecting wheat leaves, of which the preventative activity of compound D8 was almost equal to that of the positive agents. Transmission electron microscopy (TEM) observation revealed that the plasma membrane in the C4-treated F. graminearum hyphal cells was severely contracted and separated with the cell wall, coupling with the visible lysosomes and the disappeared cytoplasm and organelles, which may be the reasons for the shriveled and even ruptured hyphae observed by scanning electron microscopy (SEM). Subsequently, transcriptomics and metabolomics were performed to further elucidate the fungicidal mechanism. The regulatory networks of differential genes and metabolites in plasma membrane-related sphingolipid metabolism, linoleic acid metabolism, α-linoleic acid metabolism, and arachidonic acid metabolism were constructed and elaborated. Additionally, preliminary investigation of seeding growth suggested that compounds C4 and D8 may have different degrees of influence on the growth indicators of wheat seedlings; however, this effect may be negligible as the plant grows.

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“…38 Similarly, in the eld of medicinal chemistry and drug design, the electrical dipole moment plays an important role as a descriptor in the quantitative-structureactivity-relationship (QSAR) in order to discover the biological activity of either the natural products or the synthetic compounds. 39,40 For instance, Riahi and coworkers 41 have computed the effect of Efavirenz drug (as a potentially anticancer drug) on DNA to reveal the nature of the intermolecular interaction between them. Their results showed that the appropriate interaction is composed of the electrostatic and dispersion forces at the drug-nucleobase interface leading to the stability of the complexes.…”

Section: Introductionmentioning

confidence: 99%