Synthesis of some novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives from terephthaloyl and isophthaloyl chlorides

Mobinikhaledi, Akbar; Foroughifar, Naser; Rafiee, Abdolhossein

doi:10.1515/hc-2013-0035

Cited by 7 publications

(4 citation statements)

References 19 publications

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“…The obtained solids were recrystallized from aqueous DMSO to afford 5,5′-(1,4-phenylene)bis(4H-1,2,4-triazole-3thiols) 3a-3d. The spectral data of triazoles 3a [20], 3b [16], and 3d [16] were in full agreement with the reported data. The spectral data of compound 3c confirmed the proposed structure.…”

Section: Resultssupporting

confidence: 90%

“…The synthesis of target bis-triazolylbenzene derivatives is outlined in Schemes 1 and 2. Initially, terephthalic acid hydrazide (1) was refluxed with substituted isothiocyanates in ethanol for 5-7 h according to literature procedures [20]. After cooling, a solid product precipitated from the reaction mixture.…”

Section: Resultsmentioning

confidence: 99%

“…Similarly, isophthalic acid hydrazide 5 was refluxed with phenyl or methyl isothiocyanate in ethanol to give 6a and 6b, respectively. Without further purification, bis-thiosemicarbazide derivatives 6a and 6b were converted to bis-1,2,4-triazole-3-thiols 7a and 7b via wellstudied intramolecular dehydrative cyclization following reported procedure [20] (Scheme 2). Spectroscopic data of triazoles 7a and 7b were in full agreement with the reported results.…”

Section: Resultsmentioning

confidence: 99%

“…Commercially available fine chemicals and solvents were purchased from Aldrich and were used as received without further purification. Terephthalic acid hydrazide (1) and isophthalic acid hydrazide (5) were prepared according to reported procedures [20].…”

Section: Experimenalmentioning

confidence: 99%

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Synthesis and Antiproliferative and Antilipolytic Activities of a Series of 1,3- and 1,4-Bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzenes

et al. 2021

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A series of 1,3 and 1,4-bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzene derivatives were synthesized by the reac tion of isophthalic and terephthalic acid hydrazides with methyl and aryl isothiocyanates, followed by base-catalyzed cyclization and alkylation of the resulting bis-triazolethiols with alkyl bromides. The suggested obesity-colorectal cancer association initiated evaluation of the antiproliferative activity of the newly syn thesized compounds against a panel of obesity-related colorectal cells and inhibition of pancreatic lipase (PL). In vitro enzymatic, colorimetric, and cell culture bioassays were carried out with respective reference agents. Among the tested compounds, 1,3-bis{5-[(4-bromobenzyl)sulfanyl]-4-methyl-4H-1,2,4-triazol-3-yl}ben zene showed clearly promising, though unselective, cytotoxicity in HT29, HCT116, SW620, CACO2, and SW480 cancer cells with a PL-IC 50 value of 9.57±1.21 μM (<10 μM). Hence, the pharmacophores of most promising compounds can be druggable leads with a novel duality of antidiabesity-antineoplastic capacities and optimized potency and safety. Mechanistic examinations for hindrance of lipolysis catalysis and apoptogenic growth inhibition propensity may be attempted.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Experimenalmentioning

confidence: 99%

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Synthesis and Antiproliferative and Antilipolytic Activities of a Series of 1,3- and 1,4-Bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzenes

et al. 2021

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Design, synthesis and antitumor activity of new naproxen based 1,2,4-triazole-Schiff base derivatives

Alsenani

2023

J.Umm Al-Qura Univ. Appll. Sci.

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In the present work, new Naproxen based 1,2,4-triazole-Schiff base derivatives have been synthesized and screened for in vitro antitumor activity and in silico pharmacokinetic studies. The structure of the newly synthesized compounds (5–12) was elucidated by IR, NMR and mass spectrometry. All the compounds were tested against breast MCF-7, hepatocellular Huh-7 and lung A-549 cancer cell lines using MTT assay. Compound 7 was better in killing A549 cells with IC50 3.71 µM (1.48 fold), compared with Doxorubicin (IC50 5.50 µM). Also, compound 7 was found to be non toxic on MRC-5 normal cells as it depicts IC50 more than 500 μM. Besides, compound 12 also revealed promising activity with IC50 6.94 and 3.33 µM against MCF-7 and Huh-7 respectively. The in silico studies displayed that the synthesized compounds favors the desired pharmacokinetic profile and drug likeness properties. It can be concluded that these new Naproxen based 1,2,4-triazole-Schiff base derivative (7) has the potential to be further investigated as lead molecule in the development of new chemotherapeutic agent.

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Preparation of a thermoset polymeric membrane with shape memory and inherent self-healing properties

Davarpanah,

Abdolmaleki

2024

Polymer Testing

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Synthesis of some novel bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives from terephthaloyl and isophthaloyl chlorides

Cited by 7 publications

References 19 publications

Synthesis and Antiproliferative and Antilipolytic Activities of a Series of 1,3- and 1,4-Bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzenes

Synthesis and Antiproliferative and Antilipolytic Activities of a Series of 1,3- and 1,4-Bis[5-(R-sulfanyl)-1,2,4-triazol-3-yl)benzenes

Design, synthesis and antitumor activity of new naproxen based 1,2,4-triazole-Schiff base derivatives

Preparation of a thermoset polymeric membrane with shape memory and inherent self-healing properties

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