Reactions with hydrazonoyl halides 66: Synthesis of some new 1,3,4-thiadiazoles, triazolino[4,3-a]pyrimidines and isoxazolo[3,4-d]pyridazines containing coumarin moiety

Abdelhamid, Abdou O.; Fahmi, Abdelgawad A.; Ali, Abeer Bahlol

doi:10.5155/eurjchem.2.4.544-551.478

Cited by 6 publications

(4 citation statements)

References 26 publications

(19 reference statements)

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“…The identities of the products were concluded based on some spectroscopic data, although infrared carbonyl stretching data were inconclusive, there was a distinct pattern in the chemical shifts associated with the carbonyl resonance in the 13 C data. For example the two substituted products 5a and b showed carbonyl carbons resonances around 166-167 ppm, These values were consistent with some appropriate data shown by similar compounds obtained by other researchers in literature [10][11][12][18][19][20][21][22][23][24][25]; hence, based on these, one can conclude that structure 5 is the correct structure for the reaction product rather than its isomer 6. It is so clear to say that in structure 5 the carbonyl group is adjacent to sp 3hybrisized nitrogen atom while in the isomer 6 it is adjacent to more electronegative sp 2 -hybridized nitrogen atom in which the carbonyl carbon chemical shift should show more downfield values than those reported in literature.…”

Section: Resultssupporting

confidence: 90%

Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives

Gomha

Badrey

2013

Eur. J. Chem.

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Section: Resultssupporting

confidence: 90%

Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives

Gomha

Badrey

2013

Eur. J. 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 66: Synthesis of some new 1,3,4-thiadiazoles, triazolino[4,3-a]pyrimidines and isoxazolo[3,4-d]pyridazines containing coumarin moiety

Abstract: Reactions with hydrazonoyl halides 66: Synthesis of some new 1,3,4-thiadiazoles, triazolino[4,3-a]pyrimidines and isoxazolo[3,4-d]pyridazines containing coumarin moiety

Cited by 6 publications

References 26 publications

Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives

Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives

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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