Design, synthesis, biological activity and density function theory study of pyrazole derivatives containing 1,3,4-thiadiazole moiety

Ding, Xiao-Ming; Zhai, Zhi-Wen; Lv, Lu-Ping; Sun, Zheng; Liu, Xinghai

doi:10.1007/s11705-017-1634-2

Cited by 11 publications

(5 citation statements)

References 23 publications

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“…The structure-activity relationship of compounds 83a and 83l was also studied by density function theory method. 33…”

Section: -Herbicidal Activitymentioning

confidence: 99%

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A Review on Synthesis, Therapeutic, and Computational Studies of Substituted 1, 3, 4 Thiadiazole Derivatives

Shamroukh

Hegab²

2020

Egypt. J. Chem.

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Several studies have been reported on 1,3,4-thiadiazole and their derivatives because of their wide range of therapeutic activities. Many drugs containing thiadiazole derivatives are available in market such as acetazolamide, methazolamide, sulphamethazole, cefazoline. This review article highlights the recently synthesized 1,3,4-thiadiazole possessing important therapeutic activities and Computational Studies.

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“…The structure-activity relationship of compounds 83a and 83l was also studied by density function theory method. 33…”

Section: -Herbicidal Activitymentioning

confidence: 99%

“…H 2 SO 4 to give the corresponding 1,3,4thiadiazole derivative 40 with a low yield (Scheme 20). 33 Kubota et. al, described a reaction between benzamidrazone (41) and carbon disulfide to obtain the thiadiazole 42 (Scheme 21).…”

Section: Introductionmentioning

confidence: 99%

A Review on Synthesis, Therapeutic, and Computational Studies of Substituted 1, 3, 4 Thiadiazole Derivatives

Shamroukh

Hegab²

2020

Egypt. J. Chem.

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“…The anti-tumour potential of the 2-amino-1,3,4thiadiazole skeleton is known for long and further its fused derivatives with imidazo[2,1-b] ring system has resulted in compounds exhibiting potential diuretics, [15] antiglaucoma, [16] anticonvulsant or antiinfective [17] drug. Consequently, many imidazo[2,1-b] [1,3,4]thiadiazole derivatives have been reported to possess antitumor properties and are known to exhibit a broad spectrum of biological activities such as antitubercular, [18] anaesthetic, [19] antibacterial, 20] anticonvulsant, [21] antiinflammatory, [22] antifungal, [23] antipyretic, [24] anthelmintic, [25] analgesic, [26] cardiotonic, 27] leishmanicidal, [28] diuretic, [29] and herbicidal [30] activities. Megazol (Figure 1) are veteran anthelmintic.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Sagar,

Kumara,

et al. 2023

ChemistrySelect

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The microwave‐assisted synthesis, crystallographic studies, in‐silico docking and the evaluation of in‐vitro biological activities of 2‐(3,4‐dimethoxy)‐6‐(substituted phenyl)‐ imidazo[2,1‐b][1,3,4]thiadiazole‐5‐carbaldehydes is represented here. Single‐crystal X‐ray diffraction experiments were used to identify the crystal structure of the 6‐(4‐chlorophenyl)‐2‐(3,4‐dimethoxybenzyl)imidazo[2,1‐b][1,3,4]thiadiazole‐5‐carbaldehyde. Using fingerprint plots, Hirshfeld surface analysis was used to confirm the contributions of distinct intermolecular interactions in the development of the crystal packing. Further, density functional theory calculations were employed to calculate the molecule's electronic properties. The chemically active regions on the molecule are identified by analysing the molecular electrostatic potential map. in‐silico studies revealed that the molecules can be effectively used as antibacterial agents by taking the 3q82 receptor with chloramphenicol as a standard. As compared to the chloramphenicol standard, in‐vitro tests showed that molecules 4 a, 4 b, 4 c, and 4 f had a zone of inhibition that ranged from 9 to 11 mm against both Gram‐positive (Bacillus subtilis) and Gram‐negative (Escherichia coli) bacteria. The minimum inhibitory concentration was between 40 to 70 μg/ml. These compounds′ Hydroxyl free radical scavenging activity was between 40 to 85 %. Whereas, DPPH radical scavenging activity was between 40 and 70 %. Percentage hemolysis or cell protective activity of the compounds was ineffective at 20–40 %.

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“…Over the past few decades, many new pesticides containing carboxamide moiety, such as fluxapyroxad, penflufen, and isoflucypram, had been developed. Meanwhile, 1, 3, 4-thiadiazole thioether unit had played an important role in the field of agricultural chemistry, including antibacterial [16,25], antifungal [26,27], antiviral [28][29][30][31], insecticidal [32], and herbicidal [33] properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivity Evaluation of Novel Thiochroman-4-One Derivatives Incorporating Carboxamide and 1, 3, 4-Thiadiazole Thioether Moieties

Xiao

et al. 2022

Journal of Chemistry

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A series of novel thiochroman-4-one derivatives incorporating carboxamide and 1, 3, 4-thiadiazole thioether moieties were synthesized. Bioassay results indicated that the EC50 values of compound 6-chloro-N-(5-(methylthio)-1, 3, 4-thiadiazol-2-yl)-4-oxothiochromane-2-carboxamide (5a) against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. Citri (Xac) were 24 and 30 μg/mL, respectively, which were even better than those of bismerthiazol and thiadiazole copper. Meanwhile, compound 6-methyl-4-oxo-N-(5-(propylthio)-1, 3, 4-thiadiazol-2-yl)thiochromane-2-carboxamide (5m) showed a better antifungal activity against Botrytis cinerea (B. cinerea), with an inhibition rate of 69%, than carbendazim. As far as we know, this is the first report on the antibacterial and antifungal activities of this series of novel thiochroman-4-one derivatives incorporating carboxamide and 1, 3, 4-thiadiazole thioether moieties.

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Design, synthesis, biological activity and density function theory study of pyrazole derivatives containing 1,3,4-thiadiazole moiety

Cited by 11 publications

References 23 publications

A Review on Synthesis, Therapeutic, and Computational Studies of Substituted 1, 3, 4 Thiadiazole Derivatives

A Review on Synthesis, Therapeutic, and Computational Studies of Substituted 1, 3, 4 Thiadiazole Derivatives

Microwave‐Assisted Synthesis and Characterization of Some Aldehyde Derivatives of Imidazo[2,1‐b][1,3,4]thiadiazole: Crystal Structure Insights, In‐Silico and Biological Studies

Synthesis and Bioactivity Evaluation of Novel Thiochroman-4-One Derivatives Incorporating Carboxamide and 1, 3, 4-Thiadiazole Thioether Moieties

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