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

Shamroukh, Ahmed H.; Hegab, Mohamed I.

doi:10.21608/ejchem.2020.25343.2492

Cited by 4 publications

(3 citation statements)

References 59 publications

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“…In 2020, Hegab [18] highlighted the recently synthesized 1,3,4-thiadiazole derivatives possessing important therapeutic activities and computational studies. The preparation of a novel series of 6-arylaminomethyl-3-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles by the cyclocondensation of 5-substituted-4-amino-3-mercapto-1,2,4-triazoles with appropriately substituted anilino acetic acids employing phosphorous oxychloride was reported by Kalluraya [21].…”

Section: Rcho + Nhmentioning

confidence: 99%

Synthesis of 1,3,4-thiadiazole Derivative Using Appropriate Reaction Conditions

Kadu¹,

Masand²

2022

IJRASET

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Five membered heterocyclic rings possessing a mixture of different heteroatoms like S, N, O, etc. not only possess interesting chemical properties but also have a myriad number of biological activities. Of these, 1,3,4-thiadiazole moiety and its derivatives have gained a deep interest in recent year due to their crucial role in wide variety of drugs, dyes, and other substances of high interests. The present work is focussed on the different methods of their synthesis. The review highlights the key features of their synthesis

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Section: Rcho + Nhmentioning

confidence: 99%

Synthesis of 1,3,4-thiadiazole Derivative Using Appropriate Reaction Conditions

Kadu¹,

Masand²

2022

IJRASET

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“…Several synthetic protocols for the preparation of 1,3,4-thiadiazole-containing bioactive compounds have been developed and summarised [2,8,17,[27][28][29][30][31][32][33], the main part based on ring-closure reactions. Variable procedures are applied, like intramolecular cyclization of thiosemicarbazides [15,25] or potassium salt of hydrazinodithio formate [34] in concentrated sulphuric acid, condensation of thiosemicarbazide with carboxylic acids [35], benzoic acids [36,37], or N-arylsulfonylated amino acids [38], thiocarbohydrazides with aldehydes [39], hydrazinecarbodithioates or thiosemicarbazones with hydrazonoyl chlorides [40], sulfonamide diazonium chlorides with phenacyl thiocyanate [41], etc.…”

Section: Introductionmentioning

confidence: 99%

Functionalization of 2-Mercapto-5-methyl-1,3,4-thiadiazole: 2-(ω-Haloalkylthio) Thiadiazoles vs. Symmetrical Bis-Thiadiazoles

Petkova,

Rusew,

Shivachev

et al. 2024

Molecules

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A study on the functionalisation of 2-mercapto-5-methyl-1,3,4-thiadiazole has been conducted, yielding two series of products: 2-(ω-haloalkylthio)thiadiazoles and symmetrical bis-thiadiazoles, with variable chain lengths. The experimental conditions were optimised for each class of compounds by altering the base used and the reagents’ proportions, leading to the development of separate protocols tailored to their specific reactivity and purification needs. The target halogenide reagents and bis-thiadiazole ligands were obtained either as single products or as mixtures easily separable by chromatography. Characterisation of the products was performed using 1D and 2D NMR spectra in solution, complemented by single crystal X-ray diffraction (XRD) for selected samples, to elucidate their structural properties.

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“…The presence of a heterocyclic sulfur atom determines the high lipophilicity of thiadiazole derivatives, which gives them the ability to penetrate cell membranes easily (Haider et al 2015). It is known that 1,3,4-thiadiazole is the basis for the creation of drugs with various pharmacological activities (Li et al 2013;Haider et al 2015;Abdelriheem et al 2017;Hegab and Shamroukh 2020). A number of 1,3,4-thiadiazole derivatives have a pronounced antiepileptic activity (Raj et al 2015).…”

Section: Introductionmentioning

confidence: 99%

Design and evaluation of pharmacological properties of a new 1,3,4-thiadiazolylamide derivative of 2-propylpentanoic acid

Malygin¹,

Yasnetsov²

2021

RRP

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Introduction: The use of the pharmacophoric approach is a promising direction for modifying the chemical structure of 2-propylpentanoic (valproic) acid in order to obtain new drugs. Materials and methods: In the experiments on mice, acute toxicity, neurotoxicity, antiepileptic activity and analgesic effect of N-(5-ethyl-1,3,4-thiadiazol-2-yl)-2-propylpentanamide (valprazolamide) were evaluated. LD50 was determined by probit analysis. Neurotoxicity was determined in a rotarod test and a bar test in mice. The effects of valprazolamide on the exploratory behavior of mice in open field test and in a light/dark transition test were evaluated. Its antiepileptic activity was tested in mice against seizures induced by maximal electroshock, pentylenetetrazole (scPTZ); isoniazid, thiosemicarbazide, pilocarpine, and camphor. The analgesic effect was studied in a hot plate test. Results and discussion: N-(5-ethyl-1,3,4-thiadiazol-2-yl)-2-propylpentanamide was obtained by introducing pharmacophores into the structure of 2-propylpentanoic acid: a substituted amide group and an electron-donor domain of 1,3,4-thiadiazole. The LD50 value for intraperitoneal administration of a new 2-propylpentanoic acid: derivative to mice was 924.8 mg/kg, and the TD50 value in the rotarod test and the bar test were 456.7 mg/kg and 546.7 mg/kg, respectively. The suppression of orienting responses in the animals was noted when it was administered in neurotoxic doses. Valprazolamide showed the most antiepileptic activity on models of MES, scPTZ and isoniazid antagonism tests. The ED50 values were 138.4 mg/kg, 74.5 mg/kg, and 126.8 mg/kg, respectively. The therapeutic indices for these models of epilepsy were 6.7; 12.4; 7.3, and protective index – 3.3; 6.1 and 3.6, respectively. In the hot plate test, valprazolamide increased the latency period before a defensive response to a thermal stimulus (ED50 165 mg/kg). Conclusion: N-(5-ethyl-1,3,4-thiadiazol-2-yl)-2-propylpentanamide is a new 1,3,4-thiadiazolylamide derivative of 2-propylpentanoic acid with antiepileptic and analgesic activities, which belongs to the group of low-toxic agents. Graphic abstract N-(5-ethyl-1,3,4-thiadiazol-2-yl)-2-propylpentanamide (3D) LD50=924.8 mg/kg (mice, intraperitoneally) TD50=456.7 mg/kg (rotarod, mice, intraperitoneally) ED50=138.4 mg/kg (MES, mice, intraperitoneally) ED50=74.5 mg/kg (scPTZ, mice, intraperitoneally)

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

Cited by 4 publications

References 59 publications

Synthesis of 1,3,4-thiadiazole Derivative Using Appropriate Reaction Conditions

Synthesis of 1,3,4-thiadiazole Derivative Using Appropriate Reaction Conditions

Functionalization of 2-Mercapto-5-methyl-1,3,4-thiadiazole: 2-(ω-Haloalkylthio) Thiadiazoles vs. Symmetrical Bis-Thiadiazoles

Design and evaluation of pharmacological properties of a new 1,3,4-thiadiazolylamide derivative of 2-propylpentanoic acid

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