REACTIONS WITH HYDRAZONOYL HALIDES XXIV<sup>[1]</sup>: SYNTHESIS OF SOME NEW UNSYMMETRICAL AZINES AND DIHYDRO-1,3,4-THIADIAZOLES

Abdelhamid, Abdou O.; Mohamed, Gaber S.

doi:10.1080/10426509908031623

Cited by 6 publications

(4 citation statements)

References 9 publications

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“…Analogously, methyl cyclocarbodithioates 11–13 [45] were reacted with N ‐(4‐nitrophenyl)‐ C ‐(furan‐2‐yl)methanohydrazonoyl chloride 1 under the same conditions to afford the corresponding 1,3,4‐thiadiazole derivatives 14–16 (Scheme 3). Elemental and spectral data verified the structures of the latter products (see Experimental).…”

Section: Resultsmentioning

confidence: 99%

“…The elemental analyses were performed at Microanalytical Center, Cairo University. N ‐(4‐Nitrophenyl)‐ C ‐(furan‐2‐yl)meth‐anohydrazonoyl chloride 1 , [40, 41] 2‐((methylthio)carbonthioyl)hydrazones 3 , 7 , 8 and 11–13 , [42–45] 1‐(3‐(furan‐2‐yl)‐5‐methyl‐1‐(4‐nitrophenyl)‐1 H ‐pyrazol‐4‐yl)ethan‐1‐one 17 , [46] methyl hydrazinecarbodithioate 18 [47, 48] and hydrazonoyl chlorides 20a‐e [49–53] were prepared using the reported procedures.…”

Section: Methodsmentioning

confidence: 99%

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Design, synthesis and in‐vitro evaluation of new furan‐substituted thiadiazolyl hydrazone derivatives as promising antimicrobial agents

Helmy

Sroor

Othman

et al. 2022

Journal of Heterocyclic Chem

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Seventeen new furan‐substituted thiadiazolyl hydrazone derivatives bearing 4‐nitrophenyl moiety were designed, synthesized and tested for their in vitro antimicrobial activity. Reaction of N‐(4‐nitrophenyl)‐C‐(furan‐2‐yl)methanohydrazonoyl chloride 1 with 2‐((methylthio)carbonthioyl)hydrazine derivatives 3, 7, 8 and 11–13 in absolute ethanol in the presence of triethylamine at room temperature afforded the corresponding 1,3,4‐thiadiazole derivatives 6, 9, 10 and 14–16. Refluxing of 1‐(3‐(furan‐2‐yl)‐5‐methyl‐1‐(4‐nitrophenyl)‐1H‐pyrazol‐4‐yl)ethan‐1‐one 17 with methyl hydrazinecarbodithioate 18 in absolute ethanol in the presence of few drops of hydrochloric acid yielded methyl‐2‐(1‐(3‐(furan‐2‐yl)‐5‐methyl‐1‐(4‐nitrophenyl)‐1H‐pyrazol‐4‐yl)ethylidene)hydrazine‐1‐carbodithioate 19. The compound 19 was reacted with hydrazonoyl halides 20a‐e in absolute ethanol in the presence of triethylamine afforded the corresponding 1,3,4‐thiadiazoles 24a‐e. The specified compounds were tested for antimicrobial activity against selected model microorganisms. Antimicrobial studies revealed that compounds 6c, 6d and 15 against E. coli, compounds 6b, 6c, 10, 14, 15, 24b and 24c against B. mycoides, and compounds 14, 16, 19 and 24d against C. albicans outperformed other developed compounds in terms of antimicrobial activity.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Design, synthesis and in‐vitro evaluation of new furan‐substituted thiadiazolyl hydrazone derivatives as promising antimicrobial agents

Helmy

Sroor

Othman

et al. 2022

Journal of Heterocyclic Chem

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“…1-(1-(4-bromophenyl)-5-methyl-1 H -1,2,3-triazol-4-yl)ethanone ( 1 ) [35]. 3-(1-(4-bromophenyl)-5-methyl-1 H -1,2,3-triazol-4-yl)-1-phenyl-1 H -pyrazole-4-carbaldehyde ( 2 ) [11], methyl hydrazinecarbodithioate ( 3 ) [36] and hydrazonoyl halides 5a – i [37,38,39] were prepared as previously reported.…”

Section: Methodsmentioning

confidence: 99%

Toward Rational Design of Novel Anti-Cancer Drugs Based on Targeting, Solubility, and Bioavailability Exemplified by 1,3,4-Thiadiazole Derivatives Synthesized Under Solvent-Free Conditions

et al. 2019

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The 1,3,4-thiadiazole derivatives (9a–i) were synthesized under solvent free conditions and their chemical composition was confirmed using different spectral tools (IR, Mass, and NMR spectrometry). All the synthesized compounds were screened for their anti-cancer potentiality over human breast carcinoma (MCF-7) and human lung carcinoma (A-549). Most of the tested compounds showed remarkable anti-breast cancer activity. However, compound 4 showed the most anti-lung cancer activity. Then, compounds with cytotoxic activity ≥ 80% over breast and lung cells were subjected to investigate their specificity on human normal skin cell line (BJ-1). Compounds 9b and 9g were chosen owing to their high breast anti-cancer efficacy and their safety, in order to study the possible anti-cancer mode of action. Otherwise, drug delivery provides a means to overcome the low solubility, un-targeted release, and limited bioavailability of the prepared 1,3,4-thiadiazole drug-like substances. Compounds 9b and 9g were chosen to be encapsulated in Na-alginate microspheres. The release profile and mechanism of both compounds were investigated, and the results revealed that the release profiles of both microspheres showed a sustained release, and the release mechanism was controlled by Fickian diffusion. Accordingly, these compounds are promising for their use in chemotherapy for cancer treatment, and their hydrophilicity was improved by polymer encapsulation to become more effective in their pharmaceutical application.

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“…Imidazo [2,1-b]thiazoles 1 [43,44] methyl hydrazine carbodithioate 2 [45] and hydrazonoyl halides 4a-j and 7-9 [46][47][48] were prepared as previously reported. General procedure: To a blend of methyl carbodithioate 3 (0.37 g, 1 mmol) and the proper hydrazonoyl halide 4a-i (1 mmol) in ethanol (20 mL), triethylamine (0.5 mL) was included, the blend was then mixed at room temperature for 2-4 h (checked with TLC).…”

Section: Experimental Instrumentationmentioning

confidence: 99%

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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REACTIONS WITH HYDRAZONOYL HALIDES XXIV^[1]: SYNTHESIS OF SOME NEW UNSYMMETRICAL AZINES AND DIHYDRO-1,3,4-THIADIAZOLES

Cited by 6 publications

References 9 publications

Design, synthesis and in‐vitro evaluation of new furan‐substituted thiadiazolyl hydrazone derivatives as promising antimicrobial agents

Design, synthesis and in‐vitro evaluation of new furan‐substituted thiadiazolyl hydrazone derivatives as promising antimicrobial agents

Toward Rational Design of Novel Anti-Cancer Drugs Based on Targeting, Solubility, and Bioavailability Exemplified by 1,3,4-Thiadiazole Derivatives Synthesized Under Solvent-Free Conditions

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

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REACTIONS WITH HYDRAZONOYL HALIDES XXIV[1]: SYNTHESIS OF SOME NEW UNSYMMETRICAL AZINES AND DIHYDRO-1,3,4-THIADIAZOLES

Cited by 6 publications

References 9 publications

Design, synthesis and in‐vitro evaluation of new furan‐substituted thiadiazolyl hydrazone derivatives as promising antimicrobial agents

Design, synthesis and in‐vitro evaluation of new furan‐substituted thiadiazolyl hydrazone derivatives as promising antimicrobial agents

Toward Rational Design of Novel Anti-Cancer Drugs Based on Targeting, Solubility, and Bioavailability Exemplified by 1,3,4-Thiadiazole Derivatives Synthesized Under Solvent-Free Conditions

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

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REACTIONS WITH HYDRAZONOYL HALIDES XXIV^[1]: SYNTHESIS OF SOME NEW UNSYMMETRICAL AZINES AND DIHYDRO-1,3,4-THIADIAZOLES