5351-71-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Thienyl)ethanone thiosemicarbazone is used as an anticancer agent for its ability to inhibit the growth of cancer cells. Research has shown its potential to be a promising candidate for the development of new cancer treatments.
Used in Antioxidant Applications:
1-(2-Thienyl)ethanone thiosemicarbazone is used as an antioxidant due to its reported antioxidant properties. It has the potential to be further explored and developed as a natural antioxidant for various applications, including in the pharmaceutical and food industries.
Used in Antimicrobial Applications:
1-(2-Thienyl)ethanone thiosemicarbazone is used as an antimicrobial agent for its demonstrated antimicrobial properties. It has the potential to be developed as a new antimicrobial compound for use in various industries, such as healthcare and agriculture, to combat microbial infections.

InChI:InChI=1/C7H9N3S2/c1-5(9-10-7(8)11)6-3-2-4-12-6/h2-4H,1H3,(H3,8,10,11)

Upstream product

• 88-15-3 2-Acetylthiophene 
• 4346-94-5 thiosemicarbazide hydrochloride 
• 79-19-6 thiosemicarbazide 

Downstream Products

• 36941-46-5 1-thiophen-2-yl-ethanone (4-phenyl-thiazol-2-yl)-hydrazone 
• 36941-49-8 1-thiophen-2-yl-ethanone (4-p-tolyl-thiazol-2-yl)-hydrazone 
• 36941-47-6 1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(1-(thiophen-2-yl)ethylidene)hydrazine 
• 36941-48-7 1-thiophen-2-yl-ethanone [4-(4-bromo-phenyl)-thiazol-2-yl]-hydrazone 
• 36941-50-1 1-(4-(4-methoxyphenyl)thiazol-2-yl)-2-(1-(thiophen-2-yl)ethylidene)hydrazine 
• 1623025-77-3 3-benzyl-2-(2-(1-(thiophen-2-yl)ethylidene)hydrazono)thiazolidin-4-one 

Relevant academic research and scientific papers

Eco-friendly sequential one-pot synthesis, molecular docking, and anticancer evaluation of arylidene-hydrazinyl-thiazole derivatives as CDK2 inhibitors

One current approach in the treatment of cancer is the inhibition of cyclin dependent kinase (CDK) enzymes with small molecules. CDK are a class of enzymes, which catalyze the transfer of the terminal phosphate of a molecule of ATP to a protein that acts

Mn(II) and Cu(II) complexes of a bidentate Schiff's base ligand: Spectral, thermal, molecular modelling and mycological studies

Complexes of manganese(II) and copper(II) of general composition M(L) 2X2 have been synthesized [L = 2-acetyl thiophene thiosemicarbazone and X = Cl- and NO3-]. The elemental analysis, molar conductance measurements, magnetic susceptibility measurements, mass, IR, UV, NMR and EPR spectral studies of the compounds led to the conclusion that the ligand acts as a bidentate manner. The Schiff's base ligand forms hexacoordinated complexes having octahedral geometry for Mn(II) and tetragonal geometry for Cu(II) complexes. The thermal studies suggested that the complexes are more stable as compared to ligand. In molecular modelling the geometries of Schiff's base and metal complexes were fully optimized with respect to the energy using the 6-31g(d,p) basis set. The mycological studies of the compounds were examined against the plant pathogenic fungi i.e. Rhizoctonia bataticola, Macrophomina phaseolina, Fusarium odum.

Organoplatinum(II) complexes with 2-acetylthiophene thiosemicarbazone: Synthesis, characterization, crystal structures, and in vitro antitumor activity

Novel organoplatinum(II) complexes with 2-acetylthiophene thiosemicarbazone (ATTSC) were synthesized. The reaction of K2PtCl4 with ATTSC in 1:1 and 1:2 metal to ligand ratios yielded 1 [Pt4(ATTSC-2H) 4?4DMF] and 2 [Pt(ATTSC-H)(ATTSC)Cl?3CH3OH)]. The crystal structures of these platinum chelates have been solved by single-crystal X-ray diffraction structure determinations and revealed metalation of the thiophene ring at C2 through platinum atoms. Further characterization of 1 and 2 was performed using electronic, IR, UV/vis, and NMR spectroscopies and elemental analysis. The in vitro antitumor activity of the ligand as well as 1 and 2 was determined against two different human tumor cell lines (HT-29 and HuTu-80). These tests revealed that the platinum(II) complexes are more cytotoxic than their ligand. The tetranuclear complex 1 shows higher antiproliferative activity (IC50 = 1.2 and 1.5 μM) when compared to 2 (IC50 = 3 and 5.9 μM), while the ligand has IC50 values of 8.6 and >10 μM. Compounds 1 and 2 can therefore be considered as agents with potential antitumor activity.

Synthesis and biological evaluation of anti-Toxoplasma gondii activity of a novel scaffold of thiazolidinone derivatives

We designed and synthesised novel N-substituted 1,3-thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii efficacy. This scaffold was functionalised both at the N1-hydrazine portion with three structurally different moieties and at the lactam nitrogen with substituted benzyl groups selected on the basis of our previous structure-activity relationships studies. Using three different assay methods, the compounds were assessed in vitro to determine both the levels of efficacy against the tachyzoites of T. gondii (IC50 = 5–148 μM), as well as any evidence of cytotoxicity towards human host cells (TD50 = 68 to ≥320 μM). Results revealed that ferrocene-based thiazolidinones can possess potent anti-tachyzoite activity (TI =2–64).

DNA binding properties and antibacterial activity of heterolyptic transition metal complexes with 2,2-bipyridyl and 2-acetylthiophene thiosemicarbazone

Metal complexes having the composition M(Bipy)Cl2 (where, M = Cu(II), Ni(II) and Co(II); Bipy = 2,2-bipyridyl) are reacted with 2-acetylthiophene thiosemicarbazone (ATT) to produce heteroleptic transition metal complexes with molecular formula [M(Bipy)ATT]. The complexes are characterized by mass spectra, molar conductivity, infrared and electronic spectra. Electrochemical behaviour of these metal complexes was investigated by cyclic voltammetric studies. The metal complexes show quasi reversible cyclic voltammetric responses for the Cu(II)/Cu(I) couple. The binding properties of these complexes with calf-thymus DNA have been investigated by using absorption spectrophotometry. Metal complexes are screened for their antibacterial activity by using agar well diffusion method against pathogenic bacterial strains viz. Escherichia coli and Staphylococcus aureus. Antibacterial activity of the present complexes are comparable with the activity of ciprofloxacin. The Cu(Bipy)Cl2 complex inhibits bacteria more strongly than any other complex. The Ni(Bipy)ATT complex shows more activity than the parent complex, Ni(Bipy)Cl2.

Synthesis, biological evaluation and quantitative structure-active relationships of 1,3-thiazolidin-4-one derivatives. A promising chemical scaffold endowed with high antifungal potency and low cytotoxicity

With reference to recent studies reporting on the various biological properties of the thiazolidinone scaffold, we synthesized more than a hundred compounds characterized by a 1,3-thiazolidin-4-one nucleus derivatised at the C2 with a hydrazine bridge linked to (cyclo)aliphatic or hetero(aryl) moieties, and their N-benzylated derivatives. These molecules were assayed as potential anti-Candida agents and they were shown to possess comparable, and in some cases higher biological activity than well-established topical and systemic antimycotic drugs (i.e. clotrimazole, fluconazole, ketoconazole, miconazole, tioconazole, amphotericin B). Compounds endowed with the lowest MICs underwent further testing in order to assess their cytotoxic effect (CC50) on Hep2 cells, which demonstrated their relative safety. Finally, QSAR and 3-D QSAR models were used to predict putative chemical modifications of the 1,3-thiazolidin-4-one scaffold in order to design new and potential more active compounds against Candida spp.

Anti-Candida activity and cytotoxicity of a large library of new N-substituted-1,3-thiazolidin-4-one derivatives

On the basis of the recent findings about the biological properties of thiazolidinones and taking into account the encouraging results about the antifungal activity of some (thiazol-2-yl)hydrazines, new N-substituted heterocyclic derivatives were designed combining the thiazolidinone nucleus with the hydrazonic portion. In details, 1,3-thiazolidin-4-ones bearing (cyclo)aliphatic or (hetero)aromatic moieties linked to the N1-hydrazine at C2 were synthesized and classified into three series according to the aromatic or bicyclic rings connected to the lactam nitrogen of the thiazolidinone. These molecules were assayed for their anti-Candida effects in reference to the biological activity of the conventional topic (clotrimazole, miconazole, tioconazole) and systemic drugs (fluconazole, ketoconazole, amphotericin B). Finally, we investigated the selectivity against fungal cells by testing the compounds endowed with the best MICs on Hep2 cells in order to assess their cell toxicity (CC50) and we noticed that two derivatives were less cytotoxic than the reference drug clotrimazole. Moreover, a preliminary molecular modelling approach has been performed against lanosterol 14-α demethylase (CYP51A1) to rationalize the activity of the tested compounds and to specify the target protein or enzyme.

Novel 1,3-thiazolidin-4-one derivatives as promising anti- Candida agents endowed with anti-oxidant and chelating properties

Pursuing our recent outcomes regarding the antifungal activity of N-substituted 1,3-thiazolidin-4-ones, we synthesized thirty-six new derivatives introducing aliphatic, cycloaliphatic and heteroaromatic moieties at N1-hydrazine connected with C2 position of the thiazolidinone nucleus and functionalizing the lactam nitrogen with differently substituted (NO2, NH2, Cl and F) benzyl groups. These compounds were tested to evaluate their minimum inhibitory concentration (MIC) against several clinical Candida spp. with respect to topical and systemic reference drugs (clotrimazole, fluconazole, ketoconazole, miconazole, tioconazole, amphotericin B). Moreover, anti-oxidant properties were also evaluated by using different protocols including free radical scavenging (DPPH and ABTS), reducing power (CUPRAC and FRAP), metal chelating and phosphomolybdenum assays. Moreover, for the most active derivatives we assessed the toxicity (CC50) against Hep2 human cells in order to characterize them as multi-target agents for fungal infections.

Synthesis of bis-thiazoles, bis-pyrazoles, bis-hydrazonates, and bis-triazolothiadiazoles based on bis-hydrazonoyl and bis-hydrazones

A facile synthesis of bis-thiazoles, bis-pyrazoles, and bis-hydrazonates from the reaction of bis-hydrazonoyl dichlorides with different moieties is described. Bis-triazolothiadiazoles were synthesized via oxidative cyclization of bis-hydrazones. Structures of the final product were elucidated by elemental analyses and spectral data.

Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma

Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer.