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Labanauskas, Linas; Brūkštus, Algirdas; Gaidelis, P.; Udrenaite, É. B.; Buchinskaite, V. A.; Mitskus, M. M.; Dauksas, V.

doi:10.1023/a:1010412602886

Cited by 18 publications

(30 citation statements)

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“…The yield obtained from microwave methods was better as compared to conventional method. The target compounds, 5H- [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazine derivatives (4a-o) were prepared by environmental friendly method (Scheme 2) in which the mixture of intermediate compound 3, β-diketone / β-ketoester and catalytic amount of hydrazine hydrate irradiated in microwave oven. The purity of the compounds was checked by TLC.…”

Section: Methodsmentioning

confidence: 99%

“…All data were found in accordance with the proposed structures of synthesized compounds. All the 5H- [1,2,4]triazolo [3,4-b] [1,3,4]thiadiazine derivatives (4a-o) along with some standard antibiotics and antifungal drugs were screened for their antimicrobial activities against selected bacteria and fungus. All the antimicrobial activity results are summarized in Table 1.…”

Section: Methodsmentioning

confidence: 99%

“…The solid separated out was filtered, washed thoroughly with water and crystallized from ethanol (Scheme 1). Synthesis of 5H- [1,2,4]triazolo [3,4-b] [1,3,4] thiadiazines (4a-o) A mixture of compound 3 (10 mmol), catalytic amount of hydrazine hydrate (1 mmol) and DMF (5 mL) as an energy transfer medium was exposed to microwave irradiations for 30 seconds. After that β-diketone/ β-ketoester (10 mmol) was added to the reaction mixture and again exposed to microwave irradiations intermittently at 30 seconds for three minutes.…”

Section: Microwave Irradiation Methodsmentioning

confidence: 99%

“…IR spectra were recorded in KBr on Shimdzu Affinity-1 FTIR spectrophotometer. 1 H NMR spectra were recorded on Varian Gemini 400 spectrometer (300 MHz) using TMS as an internal standard. The mass spectra were recorded using Jeol SX 102 spectrometer at 70 ev.…”

Section: Research Article Experimentalmentioning

confidence: 99%

See 3 more Smart Citations

Facile Synthesis and Antimicrobial Activities of 5H-[1,2,4]triazol[1,3,4]thiadiazine Derivatives

2014

Chem Sci Trans

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Structurally diverse new series of 5H-[1,2,4]triazolo [3,4b] [1,3,4]thiadiazine heterocycles having medicinally privileged nucleus have been synthesized by simple and solvent free environmental benign methods. A mixture of 4-amino-5-substituted-1,2,4-triazolo-3-thiol and β-diketone/ β-ketoester and catalytic amount of hydrazine hydrate exposed to microwave irradiation in microwave oven. The intermediate 4-amino-1,2,4-triazole-3-thiols were also synthesized by entirely new solvent free environmental friendly methods. The synthesized target compounds (4a-o) were characterized by elemental analysis as well as spectral studies and screened for antimicrobial activities.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Microwave Irradiation Methodsmentioning

confidence: 99%

Section: Research Article Experimentalmentioning

confidence: 99%

See 2 more Smart Citations

Facile Synthesis and Antimicrobial Activities of 5H-[1,2,4]triazol[1,3,4]thiadiazine Derivatives

2014

Chem Sci Trans

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“…22 Thiosemicarbazones have been reported to exhibit antituberculosis activity. 23,24 Besides, 1,3,4-thiadiazoles and 1,3-thiazoles and their derivatives exhibit various biological activities such as antituberculosis, 24 antimicrobial, [25][26][27] anti-inflammatory, [28][29][30] antiviral, anticonvulsant, [31][32] antihypertensive, [33][34] local anesthetic, 35 anticancer, [36][37] hypoglycemic, 38 and cytotoxic activities, among others. [39][40][41][42][43][44][45] 1,3,4-Thiadiazole and related compounds are of great interest in chemistry owing to their bioactivity of certain plant growth regulating effects as well as antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterizations of some new tetra thiosemicarbazones and their cyclization reactions; tetra 4-methyl-5-etoxycarbonyl-2,3-dihydro-1,3-thiazole and tetra 2-acetylamino-4-acetyl-4,5-dihydro-1,3,4-thiodiazole derivatives

Er¹,

Ünver²,

Sancak³

et al. 2008

Arkivoc

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Tetra-aldehyde and ketone derivatives (2a-d) which were used to obtain tetra thiosemicarbazone compounds 3a-h were synthesized via the reaction of Ethene-1,1,2,2,-tetra-yl-tetra-methylenetetra-bromide (1) with aldehydes and ketons. Then, tetra-thiosemicarbazone compounds 3a-h were obtained from the reactions of tetra-aldehyde and keton derivatives (2a-d) with thiosemicarbazite and 4-methyl thiosemicarbazite, respectively. In the same way, tetra-4-methyl-5-ethoxycarbonyl-2,3-dihydro-1,3-thiazole compounds 4a-h were synthesized via the reaction of tetra-thiosemicarbazone compounds 3a-h with ethyl-2-chloroacetoacetate. Then, tetrathiosemicarbazone compounds 3a-h were reacted with acetic anhydride, and yielded tetra-2-acetyl-amino-4-acetyl-4,5-dihydro-1,3,4-thiodiazol compounds (5a,b,c,e,f,g). They were characterized by elemental analysis, infrared, 1 H and 13 C-NMR, mass spectroscopy. Then, the microbial features of all compounds were studied by the known method.

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Novel isoxazoline‐linked 1,3,4‐thiadiazole hybrids as anticancer agents: Design, synthesis, biological evaluation, molecular docking, and molecular dynamics simulation

Oubella

Byadi

Bimoussa

et al. 2022

Archiv der Pharmazie

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In the current study, natural (R)‐carvone was utilized as a starting material for the efficient synthesis of two series of isoxazoline derivatives bearing the 1,3,4‐thiadiazole moiety. The new compounds were obtained in good yields and were characterized by 1H and 13C NMR and HRMS analysis. The newly synthesized monoterpenic isoxazoline 1,3,4‐thiadiazole and their thiosemicarbazone intermediate derivatives were evaluated for their anticancer activity in four cancer cell lines (HT‐1080, A‐549, MCF‐7, and MDA‐MB‐231). Most of the synthesized compounds exhibited moderate to high anticancer effects. Compound 13c showed the highest anticancer activity with IC50 values ranging from 19.33 ± 1.81 to 34.81 ± 3.03 µM. Further investigation revealed that compounds 12e and 13c could inhibit the cell growth of HT‐1080 and MCF‐7 cells by inducing apoptosis through caspase‐3/7 activation. The apoptotic effect was accompanied by an S phase and G2/M cell cycle arrest for 13c and 12e, respectively. Compounds 12e and 13c were assessed in silico using molecular docking and molecular dynamics. We found that compound 13c is moderately active against the caspase‐3 protein, which triggers apoptosis via intrinsic and extrinsic routes, making compound 13c a promising candidate to activate the proapoptotic protein (caspase‐3).

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Cited by 18 publications

References 0 publications

Facile Synthesis and Antimicrobial Activities of 5H-[1,2,4]triazol[1,3,4]thiadiazine Derivatives

Facile Synthesis and Antimicrobial Activities of 5H-[1,2,4]triazol[1,3,4]thiadiazine Derivatives

Synthesis and characterizations of some new tetra thiosemicarbazones and their cyclization reactions; tetra 4-methyl-5-etoxycarbonyl-2,3-dihydro-1,3-thiazole and tetra 2-acetylamino-4-acetyl-4,5-dihydro-1,3,4-thiodiazole derivatives

Novel isoxazoline‐linked 1,3,4‐thiadiazole hybrids as anticancer agents: Design, synthesis, biological evaluation, molecular docking, and molecular dynamics simulation

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