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Usage

Uses

Used in Pharmaceutical Industry:
(1E)-1-(5-chlorothiophen-2-yl)ethanone thiosemicarbazone is used as a potential pharmaceutical agent for its possible anticancer, antiviral, and antifungal properties. Due to its thiosemicarbazone structure, it may exhibit biological activities that can be harnessed for the development of new drugs to treat various diseases.
Used in Research and Development:
(1E)-1-(5-chlorothiophen-2-yl)ethanone thiosemicarbazone is used as a subject of research and development to explore its specific biological activities and potential applications. Further studies are required to determine its efficacy and safety in various therapeutic areas, which can lead to the discovery of new treatments and advancements in medicine.

Upstream product

• 6310-09-4 2-acetyl-5-chlorothiophene 
• 79-19-6 thiosemicarbazide 

Relevant academic research and scientific papers

Half-sandwich ruthenium-arene complexes with thiophen containing thiosemicarbazones: Synthesis and structural characterization

Novel conformationally rigid half-sandwich organoruthenium(II) complexes ([(η6-p-cymene)Ru(η1-S-TSC1)Cl2], (1); [(η6-p-cymene)Ru(η1-S-TSC2)Cl2], (2) and [(η6-p-cymene)Ru(η2-N,S-TSC3)Cl]Cl, (3) have been synthesized from the reaction of [{(η6-p-cymene)RuCl}2(μ-Cl)2] with the respective thiosemicarbazones TSC1(2-acetyl-5-chloro-thiophene thiosemicarbazone), TSC2(2-acetyl-5-methyl-thiophene thiosemicarbazone) and TSC3(3-thiophene aldehyde thiosemicarbazone) in a 1: 2 M ratio in methanol and all of the complexes have been characterized by elemental analysis, UV–Vis, FT-IR and1H NMR spectroscopy. The crystal structures of TSC1, TSC2and [(η6-p-cymene)Ru(η1-S-TSC2)Cl2], (2) have been determined by X-ray crystallography revealing that TSC1and TSC2, crystallized in the monoclinic space group P21/c and complex (2) show a distorted octahedral geometry around the ruthenium centre. The mononuclear complex adopts a typical three legged piano-stool geometry (a description commonly used for half–sandwich compounds) with the metal centre coordinated by two chlorides and a TSC ligand. The coordination geometry around RuIIatom is distorted octahedron with three sites occupied by the p-cymene ligand (with an ?6coordination mode) while the remaining three sites occupied by the S atom of the TSC ligand and two Cl atoms. The spectroscopic studies showed that TSC1and TSC2are coordinated to the central metal as a monodentate ligand coordinating via the thiocarbonyl sulfur atom (C[dbnd]S) in complexes (1) and (2), whereas TSC3is coordinated to ruthenium as a bidentate ligand through azomethine nitrogen (C[dbnd]N) and sulfur atom in complex (3).

4-(3-Nitrophenyl)thiazol-2-ylhydrazone derivatives as antioxidants and selective hMAO-B inhibitors: synthesis, biological activity and computational analysis

A new series of 4-(3-nitrophenyl)thiazol-2-ylhydrazone derivatives were designed, synthesised, and evaluated to assess their inhibitory effect on the human monoamine oxidase (hMAO) A and B isoforms. Different (un)substituted (hetero)aromatic substituents were linked to N1 of the hydrazone in order to establish robust structure–activity relationships. The results of the biological testing demonstrated that the presence of the hydrazothiazole nucleus bearing at C4 a phenyl ring functionalised at the meta position with a nitro group represents an important pharmacophoric feature to obtain selective and reversible human MAO-B inhibition for the treatment of neurodegenerative disorders. In addition, the most potent and selective MAO-B inhibitors were evaluated in silico as potential cholinesterase (AChE/BuChE) inhibitors and in vitro for antioxidant activities. The results obtained from molecular modelling studies provided insight into the multiple interactions and structural requirements for the reported MAO inhibitory properties.

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.

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.

Thio semicarbazone and semicarbazone inhibitors of cysteine proteases and methods of their use

The present invention relates to thio semicarbazone and semicarbazone inhibitors of cysteine proteases and methods of using such compounds to prevent and treat protozoan infections such as trypanosomiasis, malaria and leishmaniasis. The compounds also fin

Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain

American trypanosomiasis, or Chagas' disease, is the leading cause of heart disease in Latin America. Currently there is an urgent need to develop antitrypanosomal therapy due to the toxicity of existing agents and emerging drug resistance. A novel series of potent thio semicarbazone small-molecule inhibitors of the Trypanosoma cruzi cysteine protease cruzain have been identified. Some of these inhibitors have been shown to be trypanocidal. We initially discovered that 3′-bromopropiophenone thio semicarbazone (1i) inhibited cruzain and could cure mammalian cell cultures infected with T. cruzi. 3′-Bromopropiophenone thio semicarbazone showed no toxicity for mammalian cells at concentrations that were trypanocidal. Following this lead, more than 100 compounds were designed and synthesized. A specific structure-activity relationship (SAR) was established, and many potent analogues with IC50 values in the low nanomolar range were identified. Eight additional analogues were trypanocidal in a cell culture assay, and this indicates that aryl thio semicarbazone is a productive scaffold for killing the parasites. Kinetic studies show that these are time-dependent inhibitors. Molecular modeling studies of the enzyme-inhibitor complex have led to a proposed mechanism of interaction as well as insight into the SAR of the thio semicarbazone series. The nonpeptide nature of this series, small size, and extremely low cost of production suggest this is a promising direction for the development of new antitrypanosome chemotherapy.