Synthesis of Some Novel 1,4‐Phenylene‐<i>bis</i>‐thiazolyl Derivatives and Their Anti‐hypertensive α‐blocking Activity Screening

Abdelrazek, Fathy M.; Gomha, Sobhi M.; Metz, Peter; Abdalla, Mohamed M.

doi:10.1002/jhet.2633

Cited by 25 publications

(10 citation statements)

References 14 publications

(18 reference statements)

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“…In addition, many bis ‐pyrazole and bis ‐1,3,4‐thiadiazole derivatives were reported to exhibit various pharmaceutical, agrochemical, and many other applications including antibacterial, fungicidal, tuberculostatic, antiamoebic, and plant growth regulative properties . In view of these reports and in continuation of our previous works in synthesis of bioactive bis ‐heterocyclic compounds , we report herein the synthesis of bis ‐1,3,4‐thiadiazole derivatives using N′,N″ ‐([1,1′‐biphenyl]‐4,4′‐diyl) bis (2‐oxopropanehydrazonoyl chloride) as common precursor and evaluate these compounds for their antimicrobial activities.…”

Section: Introductionmentioning

confidence: 89%

Utility of Bis‐Hydrazonoyl Chlorides as Precursors for Synthesis of New Functionalized Bis‐Thiadiazoles as Potent Antimicrobial Agents

Gomha

El-Gendy

Muhammad

et al. 2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).N 0 ,N″- ([1,-4,4 0 -diyl)bis(2-oxopropanehydrazonoyl chloride) is considered to be the key intermediate for the synthesis of a variety bis-1,3,4-thiadiazole derivatives in one step methodology with good yields by reaction of with a series of hydrazinecarbodithioate derivatives 2a-e, 6a,b, and 8a-e. The assigned structures for all the newly synthesized compounds were confirmed on the basis of elemental analyses and spectral data (infrared, NMR, and mass), and the mechanisms of their formation were also discussed. Moreover, the antimicrobial activity for twelve selected products was screened, and the results obtained exploring the high potency of some of the tested compounds compared with the employed standard bactericides and fungicides. In addition, the minimum inhibitory concentration of the tested compounds was determined, and the results obtained exploring the high potency of three of the tested compounds against all the tested microorganisms.

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Section: Introductionmentioning

confidence: 89%

Utility of Bis‐Hydrazonoyl Chlorides as Precursors for Synthesis of New Functionalized Bis‐Thiadiazoles as Potent Antimicrobial Agents

Gomha

El-Gendy

Muhammad

et al. 2018

Journal of Heterocyclic Chem

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“…Continuing our work on bis-heterocycle synthesis [31][32][33][34][35], the starting compound 2,2′-(1,2-diphenylethane-1,2-diylidene)bis(hydrazinecarbothioamide) 2 was obtained via reaction of benzil 1 with thiosemicarbazide in a molar ratio of 1:2 in refluxing EtOH/drops HCl for 3 h using a published procedure [36] (Scheme 1). The second thermal degradation step was sharp and started at 270 • C. The weight losses of chitosan, CLCS and CLCS/MWCNTs composite at 500 • C were 65.46%, 57.95% and 53.29%, respectively (Table 1).…”

Section: Synthesis Of Benzil Bis-thiazolesmentioning

confidence: 99%

Cross-Linked Chitosan/Multi-Walled Carbon Nanotubes Composite as Ecofriendly Biocatalyst for Synthesis of Some Novel Benzil Bis-Thiazoles

et al. 2021

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Aminohydrazide cross-linked chitosan (CLCS) and its MWCNTs (CLCS/MWCNTs) were formulated and utilized as a potent ecofriendly basic heterogeneous biocatalyst under ultrasonic irradiation for synthesis of two novel series of benzil bis-aryldiazenylthiazoles and benzil bis-arylhydrazonothiazolones from the reaction of benzil bis-thiosemicarbazone with 2-oxo-N′-arylpropanehydrazonoyl chlorides and ethyl 2-chloro-2-(2-phenylhydrazono) acetates, respectively. The chemical structures of the newly synthesized derivatives were elucidated by spectral data and alternative methods, where available. Additionally, their yield % was estimated using a traditional catalyst as TEA and green recyclable catalysts as CLCS and CLCS/MWCNTs composite in a comparative study. We observed that, under the same reaction conditions, the yield % of the desired products increased by changing TEA to CLCS then to CLCS/MWCNT from 72–78% to 79–83% to 84–87%, respectively. The thermal stability of the investigated samples could be arranged as CLCS/MWCNTs composite > CLCS > chitosan, where the weight losses of chitosan, CLCS and CLCS/MWCNTs composite at 500 °C were 65.46%, 57.95% and 53.29%, respectively.

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“…It has been reported that such compounds possess antitumor properties against a variety of human cancer cell lines [15][16][17]. In continuation to a previous study where we deal with the utility of hydrazonoyl halides for synthesis of various bioactive bridgehead nitrogen polyheterocycles [18][19][20][21][22][23][24][25][26][27][28][29][30][31][32], we aim herein to report a new facile synthesis of new imidazo [2,1-b]thiazole-linked thiadiazole conjugates, It is anticipated that the synthesized compounds will have potent pharmacological activities as anticancer agents.…”

Section: Introductionmentioning

confidence: 97%

Synthesis, Molecular Docking Screening and Anti-Proliferative Potency Evaluation of Some New Imidazo[2,1-b]Thiazole Linked Thiadiazole Conjugates

et al. 2020

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Background: Imidazo[2,1-b]thiazole scaffolds were reported to possess various pharmaceutical activities. Results: The novel compound named methyl-2-(1-(3-methyl-6-(p-tolyl)imidazo[2,1-b]thiazol-2-yl)ethylidene)hydrazine-1-carbodithioate 3 acted as a predecessor molecule for the synthesis of new thiadiazole derivatives incorporating imidazo[2,1-b]thiazole moiety. The reaction of 3 with the appropriate hydrazonoyl halide derivatives 4a–j and 7–9 had produced the respective 1,3,4-thiadiazole derivatives 6a–j and 10–12. The chemical composition of all the newly synthesized derivatives were confirmed by their microanalytical and spectral data (FT-IR, mass spectrometry, 1H-NMR and 13C-NMR). All the produced novel compounds were screened for their anti-proliferative efficacy on hepatic cancer cell lines (HepG2). In addition, a computational molecular docking study was carried out to determine the ability of the synthesized thiadiazole molecules to interact with active site of the target Glypican-3 protein (GPC-3). Moreover, the physiochemical properties of the synthesized compounds were derived to determine the viability of the compounds as drug candidates for hepatic cancer. Conclusion: All the tested compounds had exhibited good anti-proliferative efficacy against hepatic cancer cell lines. In addition, the molecular docking results showed strong binding interactions of the synthesized compounds with the target GPC-3 protein with lower energy scores. Thus, such novel compounds may act as promising candidates as drugs against hepatocellular carcinoma.

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Synthesis of Some Novel 1,4‐Phenylene‐bis‐thiazolyl Derivatives and Their Anti‐hypertensive α‐blocking Activity Screening

Abstract: A series of novel 1,4‐phenylene‐bis‐thiazolyl derivatives were synthesized and evaluated for their anti‐hypertensive activities as α‐blocking agents and some of them showed promising activities.

Cited by 25 publications

References 14 publications

Utility of Bis‐Hydrazonoyl Chlorides as Precursors for Synthesis of New Functionalized Bis‐Thiadiazoles as Potent Antimicrobial Agents

Utility of Bis‐Hydrazonoyl Chlorides as Precursors for Synthesis of New Functionalized Bis‐Thiadiazoles as Potent Antimicrobial Agents

Cross-Linked Chitosan/Multi-Walled Carbon Nanotubes Composite as Ecofriendly Biocatalyst for Synthesis of Some Novel Benzil Bis-Thiazoles

Synthesis, Molecular Docking Screening and Anti-Proliferative Potency Evaluation of Some New Imidazo[2,1-b]Thiazole Linked Thiadiazole Conjugates

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