Optimized POCl3-assisted synthesis of 2-amino-1,3,4-thiadiazole/1,3,4-oxadiazole derivatives as anti-influenza agents

Dong, Jianghong; Pei, Qing-Lan; Wang, Panpan; Ma, Qinge; Hu, Wenhui

doi:10.1016/j.arabjc.2022.103712

Cited by 19 publications

(3 citation statements)

References 57 publications

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“…[4,5] In this context, thiazole derivatives have been reported to exhibit antioxidant, analgesic, and antimicrobial actions such as antibacterial, antifungal, antimalarial, anticancer, antiallergic, antihypertensive, anti-inflammatory, and antipsychotic properties. [6][7][8][9][10][11][12][13] Furthermore, the thiadiazole nucleus is a wellknown and important heterocyclic nucleus with numerous biological activities, including anti-microbial [14] , anticonvulsant [15] , anti-cancer [16] , anti-viral [17] , anti-tuberculosis [18] , anti-inflammatory and analgesic [19] , diuretic [20] , anti-diabetic [21] , anti-depressant [22] , anti-ulcer [23] , anti-malarial, antileishmanicidal [24] , anti-influenza [25] , anti-hypolipidemic, antihyperlipidemia [26] , anti-hypertensive. [27] The 1,3,4-thiadiazole derivatives are believed to have a variety of biological activities because of the NÀ CÀ SÀ moiety and the ring's strong aromaticity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐Bacterial Evaluation of Novel Scaffolds Based on Bis‐Thiazole or bis‐1,3,4‐Thiadiazole Linked to Thieno[2,3‐b]Thiophene as New Hybrid Molecules

Laboud,

Zahran,

Hassaneen

et al. 2024

ChemistrySelect

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The reaction of bis‐2‐(methylthiocarbonothioyl)hydrazone with the appropriate hydrazonoyl halides in 1,4‐dioxane in the presence of triethylamine at reflux yielded a novel series of bis(1,3,4‐thiadiazoles) linked to a thieno[2,3‐b]thiophene core. The reaction of the appropriate α‐ketohydrazonoyl halides or α‐haloketones with the corresponding bis(2‐carbamothioylhydrazone) in ethanol at reflux in the presence of a few drops of triethylamine produced good yields of novel bis‐thiazoles linked to the thieno[2,3‐b]thiophene core as novel hybrid molecules. Elemental analyses and spectral data were used to determine the structures of the novel compounds. The antibacterial activity of newly synthesized compounds was evaluated. The MIC determination using resazurin was studied for the most reactive compounds. The pharmacokinetic properties were evaluated by in silico ADMET analysis.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Anti‐Bacterial Evaluation of Novel Scaffolds Based on Bis‐Thiazole or bis‐1,3,4‐Thiadiazole Linked to Thieno[2,3‐b]Thiophene as New Hybrid Molecules

Laboud,

Zahran,

Hassaneen

et al. 2024

ChemistrySelect

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“…Drug resistibility is one of the major problems occurring worldwide and to deal with this, the need of synthesizing new compounds has become one of the most interesting research areas. Thiadiazole nucleus is a well-known and one of the most important heterocyclic nuclei, exhibiting various biological activities, such as anti-microbial [1][2][3][4][5], anti-convulsant [6][7][8], anti-cancer [4,9,10], anti-viral [11,12], anti-tuberculosis [12,13], anti-inflammatory and analgesic [14][15][16], diuretic [17], anti-diabetic [18,19], anti-depressant [20,21], anti-ulcer [16,22], anti-malarial, anti-leishmanicidal [23,24], anti-influenza [25,26], anti-hypolipidemic, antihyperlipidemia [27,28], anti-hypertensive [29], etc. Thiadiazole is a five-membered heterocyclic ring containing a sulfur atom, two nitrogen atoms, and hydrogen binding domain.…”

Section: Introductionmentioning

confidence: 99%

Diverse Biological Activities of 1,3,4-Thiadiazole Scaffold

2022

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The chemistry of 1,3,4-thiadiazole is one of the most interesting scaffolds for synthesizing new drug molecules due to their numerous pharmacological activities. Several modifications in the thiadiazole ring have been made, proving it to be more potent and highly effective with a less toxic scaffold for various biological activities. There are several marketed drugs containing 1,3,4-thiadiazole ring in their structure. In this review article, we have tried to compile the newly synthesized 1,3,4-thiadiazole derivatives possessing important pharmaceutical significance since 2014.

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“…1,3,4‐Oxadiazole, as an important nitrogen‐ and oxygen‐containing heterocycle, has various applications 26,27 . More importantly, it possesses diverse biological activities, including antibacterial, 28 anticancer, 29 antiviral 30 and anti‐inflammatory 31 among others. Meanwhile, sulfonate or carboxylate derivatives with broad‐spectrum biological activities have attracted the attention of a large number of agricultural researchers, and have been proven to have antifungal, 32 antiviral, 33 antibacterial, 34,35 anticancer 36 and other biological activities.…”

Section: Introductionmentioning

confidence: 99%

Novel 1,3,4‐oxadiazole sulfonate/carboxylate flavonoid derivatives: synthesis and biological activity

Peng

Liu

Zhu

et al. 2022

Pest Management Science

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Background: With the long-term use of traditional bactericides and antiviral agents, drug resistance has become increasingly prominent, resulting in impaired crop growth and yields. Based on this, the introduction of small molecular active groups into natural products has become the direction of research for green pesticides.Results: In this study, novel 1,3,4-oxadiazole sulfonate/carboxylate flavonoid derivatives were explored. Among them, D4 exhibited good inhibitory effects on plant bacteria. It is worth mentioning that D4 (15 ∼g ml −1 ) exhibited an excellent median effective concentration (EC 50 ) value against Xanthomonas oryzae pv. oryzae (Xoo), which was better than bismerthiazol (73 ∼g ml −1 ) and thiodiazole copper (100 ∼g ml −1 ). The EC 50 for D4 was much lower than the two positive controls (bismerthiazol, thiodiazole copper), making D4 more potent in this assay of bacterial growth inhibition. In addition, mechanism research using scanning electron microscopy revealed that D4 could cause deformation or rupture of the cell membranes of Xoo and Pseudomonas syringae pv. actinidiae. Moreover, D4 exhibited the best EC 50 for in vivo curative (132 ∼g ml −1 ) and protective (101 ∼g ml −1 ) activities against tobacco mosaic virus, which were more effective than ningnanmycin. Microscale thermophoresis data suggested that D4 [dissociation constant (K d ) = 0.038 ± 0.011 ∼mol L −1 ] exhibited a stronger binding capacity than the control agent ningnanmycin (K d = 4.707 ± 2.176 ∼mol L −1 ). Conclusion:The biological activity data and mode of action demonstrated that D4 had the best antibacterial and antiviral effects. Compound D4 discovered in the current work may be a very promising agricultural drug.

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Optimized POCl3-assisted synthesis of 2-amino-1,3,4-thiadiazole/1,3,4-oxadiazole derivatives as anti-influenza agents

Cited by 19 publications

References 57 publications

Synthesis and Anti‐Bacterial Evaluation of Novel Scaffolds Based on Bis‐Thiazole or bis‐1,3,4‐Thiadiazole Linked to Thieno[2,3‐b]Thiophene as New Hybrid Molecules

Synthesis and Anti‐Bacterial Evaluation of Novel Scaffolds Based on Bis‐Thiazole or bis‐1,3,4‐Thiadiazole Linked to Thieno[2,3‐b]Thiophene as New Hybrid Molecules

Diverse Biological Activities of 1,3,4-Thiadiazole Scaffold

Novel 1,3,4‐oxadiazole sulfonate/carboxylate flavonoid derivatives: synthesis and biological activity

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