Synthesis, Reactions, and Anticancer Activity of Some 1,3,4-Thiadiazole/Thiadiazine Derivatives of Carbazole

Abdel-Rahman, T. M.

doi:10.1080/10426500500536572

Cited by 16 publications

(3 citation statements)

References 6 publications

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“…23,24 The thiyl radical fragment is very important for radical scavenging and anti-proliferative effects of S-BHT. As reported, a 1,3,4-thiadiazole moiety containing compounds have exhibited potential anticancer, 25,26 antitubercular 27 and antiulcer properties. 28 The aromaticity of 1,3,4-thiadiazoles was attributed to their potential as anticancer agent.…”

Section: Introductionmentioning

confidence: 75%

Design and synthesis of sulfur-containing butylated hydroxytoluene: antioxidant potency and selective anticancer agent

et al. 2019

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In the present study, a series of multipotent antioxidants (MPAOs), namely sulfur-containing BHT (S-BHT), derivatives were rationally designed and synthesized, and their inhibitory activities against free radicals and human cancer cell lines, HT29 (colon cancer) and MCF7 (breast cancer) were further evaluated. The experimental results showed that the Six out-of-eight S-BHT compounds had excellent antioxidant activity against DPPH radical with major enhancement compared to BHT. Among them, compounds 2b, 2a and 3b attained over 45% lower IC 50 values than BHT. In vitro cytotoxicity, MTT assay was carried out using two human cancer cell lines, HT29 (colon cancer) and MCF7 (breast cancer) in addition to their non-tumorigenic counterparts to explore selectivity. In line with antioxidant activity, compounds 2a and 2b displayed the highest cytotoxicity effect on both cancer types. Interestingly, 2b not only exhibited superior cancer inhibition but also scored high selectivity index (SI = 5.2, 12.5) in colon and breast tissues, respectively, exceeding that of the standard chemotherapeutic drugs used 5-Fluorouracil (5-FU) and Tamoxifen (Tmx), with lower IC 50 values. The results indicated that the symmetric S-BHT derivatives were significantly enhanced by the antioxidant potency and their ability as useful and promising selective anticancer agents.

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Section: Introductionmentioning

confidence: 75%

Design and synthesis of sulfur-containing butylated hydroxytoluene: antioxidant potency and selective anticancer agent

et al. 2019

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“…In recent years, interest in thiadiazines has increased because of the high biological activity and broad spectrum action of their derivatives . In addition, it has been reported that certain compounds bearing a thiadiazine nucleus possess significant antimicrobial and anticancer activities. Also, thiadiazines substitution on 3‐ position of coumarin nucleus has been reported to exhibit antioxidative/ antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Some Novel Thiazoles, 1,3,4‐Thiadiazines, 1,3,4‐Thiadiazoles Incorporating Coumarin Moiety

Abdel‐Aziem

2014

Journal of Heterocyclic Chem

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Starting from 3‐acetyl‐2H‐chromen‐2‐one and hydrazinecarbothiohydrazide, new functionalized thiazoles, 1,3,4‐thiadiazines, and 1,3,4‐thiadiazoles were prepared. The structures of the compounds prepared were confirmed by both elemental and spectral analyses as well as by alternate synthesis. The antimicrobial activities of the compounds prepared were screened, and the results showed that most of such compounds exhibit considerable activities.

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“…Compounds containing the 1,3,4-thiadiazole nucleus have a wide range of pharmacological activities that include antimicrobial [ 31 ], antitubercular [ 32 ], anticancer [ 33 , 34 ] and antioxidant [ 35 ] properties.…”

Section: Introductionmentioning

confidence: 99%

Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities

et al. 2012

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A computer-aided predictions of antioxidant activities were performed with the Prediction Activity Spectra of Substances (PASS) program. Antioxidant activity of compounds 1, 3, 4 and 5 were studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and lipid peroxidation assays to verify the predictions obtained by the PASS program. Compounds 3 and 5 showed more inhibition of DPPH stable free radical at 10−4 M than the well-known standard antioxidant, butylated hydroxytoluene (BHT). Compound 5 exhibited promising in vitro inhibition of Fe2+-induced lipid peroxidation of the essential egg yolk as a lipid-rich medium (83.99%, IC50 16.07 ± 3.51 µM/mL) compared to α-tocopherol (α-TOH, 84.6%, IC50 5.6 ± 1.09 µM/mL). The parameters for drug-likeness of these BHT analogues were also evaluated according to the Lipinski’s “rule-of-five” (RO5). All the BHT analogues were found to violate one of the Lipinski’s parameters (LogP > 5), even though they have been found to be soluble in protic solvents. The predictive polar surface area (PSA) and absorption percent (% ABS) data allow us to conclude that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these new multipotent antioxidants (MPAOs) as potential antioxidants for tackling oxidative stress and lipid peroxidation processes.

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Synthesis, Reactions, and Anticancer Activity of Some 1,3,4-Thiadiazole/Thiadiazine Derivatives of Carbazole

Abstract: EgyptA novel method for the synthesis of 1,3,4-thiadiazole and 1,3,4-thiadiazine derivatives bearing a carbazole moiety is described. Carbazole was transformed into carbazole-9-thiocarbohydrazide in two steps. This compound was allowed to react with various electrophiles

Cited by 16 publications

References 6 publications

Design and synthesis of sulfur-containing butylated hydroxytoluene: antioxidant potency and selective anticancer agent

Design and synthesis of sulfur-containing butylated hydroxytoluene: antioxidant potency and selective anticancer agent

Synthesis and Antimicrobial Activity of Some Novel Thiazoles, 1,3,4‐Thiadiazines, 1,3,4‐Thiadiazoles Incorporating Coumarin Moiety

Butylated Hydroxytoluene Analogs: Synthesis and Evaluation of Their Multipotent Antioxidant Activities

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