Synthesis and diuretic activity of novel 5-amino-1,3,4-thiadiazole-2-thiol derivatives

Drapak, Іryna; Zimenkovsky, Borys; Slabyy, Mychaylo; Holota, Serhii; Perekhoda, Lina; Yaremkevych, Roksolana

doi:10.7124/bc.000a4a

Cited by 7 publications

(7 citation statements)

References 35 publications

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“…Then, 2-chloro-1-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone and catalytic amount (0.1 mmol%) of potassium iodide was added and the reaction mixture refluxed for 1.5 h. The selective alkylation of the exocyclic sulfur atom in 1 was achieved using such an approach, and intermediate compound 2 was obtained with an 81% yield. Differences in the nucleophilic properties of thiol-and amine-group in 1 were the main reason for selective alkylation, and such an approach is popular in the design of bioactive 1,3,4-thiadiazoles [27,28] In this regard, the main object of the present work was developing a fast and easy synthetic scheme for hybrid molecules containing pyrazoline, 1,2,4-thiadiazole, and dichloroacetic acid moieties, using cheap, commercially available reagents. The structure characterization of the synthesized molecule, using NMR and LC-MS spectra and in vitro anticancer activity evaluation accordingly to the "60 lines screening" algorithm (DTP NCI, USA), are presented herein as well.…”

Section: Synthesis Of the Title Compoundmentioning

confidence: 99%

“…Then, 2-chloro-1-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone and catalytic amount (0.1 mmol%) of potassium iodide was added and the reaction mixture refluxed for 1.5 h. The selective alkylation of the exocyclic sulfur atom in 1 was achieved using such an approach, and intermediate compound 2 was obtained with an 81% yield. Differences in the nucleophilic properties of thiol-and amine-group in 1 were the main reason for selective alkylation, and such an approach is popular in the design of bioactive 1,3,4-thiadiazoles [27,28]. In the next step, the acylation of the primary amino group of 2 was applied, and the commercially available dichloroacetyl chloride was used as an acylating agent.…”

Section: Synthesis Of the Title Compoundmentioning

confidence: 99%

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2,2-Dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide

Yushyn

Holota

Lesyk

2022

Molbank

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The pharmacophore hybridization approach is widely used for the design of drug-like small molecules with anticancer properties. In the present work, a “cost-effective” approach to the synthesis of the novel non-condensed pyrazoline-bearing hybrid molecule with 1,3,4-thiadiazole and dichloroacetic acid moieties is proposed. The 5-amino-1,3,4-thiadiazole-2-thiol was used as a starting reagent, and the synthetic strategy includes stepwise alkylation of the sulfur atom and acylation of the nitrogen atom to obtain the target title compound. The structure of the synthesized 2,2-dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide (yield 90%) was confirmed by 1H, 13C, 2D NMR and LC-MS spectra. Anticancer activity in “60 lines screening” (NCI DTP protocol) was studied in vitro for the title compound.

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Section: Synthesis Of the Title Compoundmentioning

confidence: 99%

“…Then, 2-chloro-1-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazol-2-yl]ethanone and catalytic amount (0.1 mmol%) of potassium iodide was added and the reaction mixture refluxed for 1.5 h. The selective alkylation of the exocyclic sulfur atom in 1 was achieved using such an approach, and intermediate compound 2 was obtained with an 81% yield. Differences in the nucleophilic properties of thiol-and amine-group in 1 were the main reason for selective alkylation, and such an approach is popular in the design of bioactive 1,3,4-thiadiazoles [27,28]. In the next step, the acylation of the primary amino group of 2 was applied, and the commercially available dichloroacetyl chloride was used as an acylating agent.…”

Section: Synthesis Of the Title Compoundmentioning

confidence: 99%

2,2-Dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide

Yushyn

Holota

Lesyk

2022

Molbank

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“…When different functional groups that interact with biological receptors are added to this ring, moiety compounds with extraordinary properties are obtained. Thiadiazoles and their derivatives have various biological and medicinal characteristics such as antimicrobial [1], anticancer [2], antibacterial, antiviral [3], antifungal [4] antitubercular [5], antihypertensive [6], anticonvulsant [7], diuretic [8], antioxidant [9] properties. They are also used for various applications such as pesticides, herbicides, and insecticides in the agriculture field [10].…”

Section: Introductionmentioning

confidence: 99%

Novel Bis-1,3,4-Thiadiazoles Derivatives: Synthesis, Spectroscopic Characterization, DFT Calculations and Evaluation of their Antimicrobial and Antioxidant Activities

Çakmak

Çavuş

2023

Cumhuriyet Science Journal

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Two new, bis-1,3,4-thiadiazoles derivatives (I and II), were prepared by cyclization reaction of oxalic acid with N-alkyl/allyl thiosemicarbazides and phosphorous oxychloride (POCl3). Then the newly prepared products screened for their antimicrobial and antioxidant activities. The biological activity results shown that tested compounds exhibited effective antibacterial activity against six different bacteria. However, the compound II demonstrated greater ABTS˙+ scavenging ability. The characterization of the synthesized molecules was done by FT-IR, 1H NMR, 13C NMR spectroscopic methods and elemental analysis. Moreover, the experimental FT-IR and NMR spectra of the molecules were compared with the results calculated at the cc-pvtz, 6-311g(2d,2p), and 6-311++g(2d,2p) levels of theory. The effect of substituted groups on the spectral and electronic properties of the compounds was investigated. NCI and QTAIM analyses were performed to examine the effects of allyl group and intramolecular interactions on σ and π bonds. How the N-H bonds of the substituted groups affect the bond degrees was investigated using Fuzzy, Laplacian and Mayer approaches, and the relationship of the data with the antioxidant properties of the compounds was examined. In addition, the relationship between bond stretching force constant and intrinsic bond strength index, electron density, and delocalization index for some bonds was revealed.

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“…Being mesoionic compounds, thiadiazoles can easily penetrate cell membranes. The thiadiazole containing compounds exhibited a wide range of activities (anti-inflammatory, antibacterial, antifungal, antiviral, cardioprotective, and an tidiabetic) [11][12][13][14][15][16]. It was reported the anti cancer activity of thiadiazole derivatives [17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, we have synthesized a derivative of thiadiazole -the compound N(5me thyl [1,3,4]thiadiazol2yl)propionamide (Fig. 1), which, as described earlier, has di uretic, cardioprotective and anti-inflammatory effects [24,25] .…”

Section: Introductionmentioning

confidence: 99%

Study of the anticancer activity of N-(5-methyl-[1,3,4]thiadiazol-2-yl)-propionamide toward human tumor cells in vitro

et al. 2023

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In vitro study and characterization of anticancer activity of new heterocyclic derivati ve -N(5methyl [1,3,4]thiadiazol2yl)propionamide. Methods. The cell culture; MTT assay. Results. We synthesized N(5methyl[1,3,4]thiadiazol2yl)propionamide, which possessed diuretic, cardioprotective, and anti-inflammatory effects. Here, we investigated its cytotoxi ci ty effect towards the tumor cell lines of various tissue origins: liver (HepG2), breast (MCF7), lung (A549), cervical (KB31), and leukemia (HL60) cells, as well as towards the non-tumor cells (НЕК293 and NIH3T3). The IC 50 values of the synthesized compound for tumor cells were in the range of 9.4-97.6 μg/mL. We found that the human hepatocellular carcinoma HepG2 cells were the most sensitive to the action of N(5methyl[1,3,4]thiadiazol 2yl)propionamide with the IC 50 value of 9.4 μg/mL. The studied derivative slightly inhibited the growth of the pseudonormal HEK293 and NIH3T3 cells. Conclusions. The antipro li fe rative activity of N(5methyl[1,3,4]thiadiazol2yl)propionamide dropped in the order: hepatocarcinoma > leukemia > breast carcinoma cells. Thus, we revealed in the molecule of N(5methyl[1,3,4]thiadiazol2yl)propionamide a combination of the diuretic, cardioprotec tive, anti-inflammatory and anticancer activities, which is of great significance for this agent as a potent anticancer medicine. K e y w o r d s: N(5methyl[1,3,4]thiadiazol2yl)propionamide, cytotoxicity in vitro, anti cancer activity.

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Synthesis and diuretic activity of novel 5-amino-1,3,4-thiadiazole-2-thiol derivatives

Cited by 7 publications

References 35 publications

2,2-Dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide

2,2-Dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide

Novel Bis-1,3,4-Thiadiazoles Derivatives: Synthesis, Spectroscopic Characterization, DFT Calculations and Evaluation of their Antimicrobial and Antioxidant Activities

Study of the anticancer activity of N-(5-methyl-[1,3,4]thiadiazol-2-yl)-propionamide toward human tumor cells in vitro

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