5351-91-7

Usage

Uses

Used in Medicinal Chemistry and Drug Development:
2-(2-Thienylmethylidene)hydrazine-1-carbothioamide is used as a chemical building block for the synthesis of new pharmaceutical compounds. Its unique structure allows it to interact with various biological targets, making it a promising candidate for the development of drugs with novel mechanisms of action.
Used in Organic Synthesis:
In the field of organic synthesis, 2-(2-Thienylmethylidene)hydrazine-1-carbothioamide serves as a versatile intermediate for the preparation of a wide range of organic compounds. Its reactivity and functional groups enable the formation of various derivatives, which can be further utilized in the synthesis of complex organic molecules.
Used in Materials Science:
2-(2-Thienylmethylidene)hydrazine-1-carbothioamide is used as a component in the development of new materials with specific properties. Its incorporation into polymers, for example, can lead to materials with improved electrical conductivity, thermal stability, or other desirable characteristics.
Further Research:
Due to the potential biological activities of 2-(2-Thienylmethylidene)hydrazine-1-carbothioamide, further research is needed to fully understand its properties and explore its potential uses in various applications. This may include investigating its interactions with biological systems, evaluating its efficacy and safety in drug development, and exploring its role in the synthesis of novel materials.

InChI:InChI=1/C6H7N3S2/c7-6(10)9-8-4-5-2-1-3-11-5/h1-4H,(H3,7,9,10)/b8-4+

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 79-19-6 thiosemicarbazide 
• 31330-51-5 ethyl (E)-2-cyano-3-(2-thienyl)-2-propenoate 

Downstream Products

• 125791-40-4 (Z)-3-(5-Amino-2-thiophen-2-yl-[1,3,4]thiadiazol-3-yl)-1-thiophen-2-yl-propenone 
• 78559-47-4 5-[1-Phenyl-meth-(Z)-ylidene]-3-{[1-thiophen-2-yl-meth-(E)-ylidene]-amino}-2-thioxo-imidazolidin-4-one 
• 78559-21-4 5-[1-Phenyl-meth-(Z)-ylidene]-2-{[1-thiophen-2-yl-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 78559-23-6 5-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2-{[1-thiophen-2-yl-meth-(E)-ylidene]-hydrazono}-thiazolidin-4-one 
• 1242658-45-2 1-(4-(3-methoxyphenyl)thiazol-2-yl)-2-(thiophen-2-ylmethylene)hydrazine 
• 618063-86-8 C₁₅H₁₃N₃S₂ 
• 618063-87-9 C₁₅H₁₃N₃OS₂ 
• 433317-13-6 N-(4-phenylthiazol-2-yl)-2-formylthiophene hydrazone 
• 1424370-25-1 C₁₂H₁₇N₃S 
• 1424370-02-4 4-cyclohexyl-3-(thiophen-2-yl)-4H-1,2,4-triazole 
• 1424370-01-3 4-(2-chlorobenzyl)-3-(thiophen-2-yl)-4H-1,2,4-triazole 
• 1424370-23-9 C₁₃H₁₂ClN₃S 
• 1424370-32-0 C₁₄H₁₄BrN₃S 
• 1424370-06-8 4-(4-bromophenethyl)-3-(thiophen-2-yl)-4H-1,2,4-triazole 

Relevant academic research and scientific papers

Synthesis, physicochemical properties, and in vitro antibacterial screening of palladium(II) complexes derived from thiosemicarbazone

A new series of PdII complexes derived from thiosemicarbazone has been synthesized. The synthesized PdII complexes have been characterized on the basis of elemental analyses, FT-IR, 1H- and 13C-NMR, UV/VIS, and thermal studies. A square-planar geometry has been assigned around PdII ions on the basis of results obtained from UV/VIS studies. The thiosemicarbazone ligand and its PdII complexes have been screened against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria in vitro as growth-inhibiting agents, and the results revealed significant antibacterial activities. Copyright

Synthesis, Characterization, and DNA-Binding Kinetics of New Pd(II) and Pt(II) Thiosemicarbazone Complexes: Spectral, Structural, and Anticancer Evaluation

In a bid to come up with potential anticancer agents, a class of thiosemicarbazone ligands bearing substituted thiophene were synthesized followed by complexation with various Pd(II) and Pt(II) metal precursors. The ligands (E)-1-((thiophen-2-yl)methylene)thiosemicarbazide (L1), (E)-1-((4-bromothiophen-2-yl)methylene)thiosemicarbazide (L2), and (E)-1-((5-bromothiophen-2-yl)methylene)thiosemicarbazide (L3) were synthesized by condensation reactions and obtained in good yields. Complexation of L1 and L2 with Pd(cod)Cl2 gave C1 (C6H7Cl2N3PdS2) and C2 (C6H6BrCl2N3PdS2), respectively. Complexation of L1 with K2PtCl4 gave C3 (C6H7Cl2N3PtS2), while L3 with K2PtCl2[(PPh)3]2 gave C4 (C24H21BrClN3PPtS2). The structures and coordination for all compounds were established by FTIR, 1H-NMR, 13C-NMR, UV-Vis, elemental analysis, and single-crystal X-ray diffraction studies for ligand L1. Tuning of the spectral and anticancer activity of the compounds was investigated by changing the position of the bromide substituent, metal center, and the σ or π-donor/acceptor strength of the groups surrounding the metal center. The compounds had low to moderate anticancer potency with their spectral and structural properties correlating with the corresponding anticancer activity profiles. DNA binding modes were studied by spectroscopy and were comparable to known DNA intercalators. Structure-activity profiles were evident especially between C1 and C2 differing by the presence of a Br in position 5 of thiophene ring, which caused a remarkable increase in IC50 values, from 14.71 ± 0.016 (C1) to 43.08 ± 0.001(C2) in Caco-2 cells, 1.973 ± 0.048 (C1) to 59.56 ± 0.010 (C2) in MCF-7 cells, 16.65 ± 0.051 (C1) to 72.25 ± 0.003 (C2) in HeLa cells, 14.64 ± 0.037 (C1) to 94.34 ± 0.003 (C2) in HepG2, and 14.05 ± 0.042 (C1) to >100(C2) in PC-3 cells.

Novel iron carbonyl complexes from thiophene-2-carboxaldehyde thiosemicarbazone

The reaction of thiophene-2-carboxaldehyde thiosemicarbazone (2-C4H3SCHNNHC(S)NH2) (1) with diiron nonacarbonyl under mild conditions in anhydrous benzene yields three iron carbonyl organometallic clusters: (i) Fe2S2 square-base pyramidal cluster 2 ([Fe(CO)3]3(μ3-S)2), (ii) Fe2S2 square-base pyramidal metal carbene cluster 3 ([Fe(CO)3]2Fe(CO)2 (μ3-S)2(C(NH2)NHNCH (2-C4H3S)), and (iii) double butterfly cluster 4 ([Fe(CO)3]3Fe(CO)2(μ4-S) (C,N; C(NH2)NHNCH(2-C4H3S) (μ2-S, N; SC(NH2)NNCH(2-C4 H3S)), and an octahedral complex 5 (Fe(CO)2(S, N; SC(NH2)NNCH (2-C4H3S))2. These products were fully characterized spectrally. The molecular structures of 1, 3, 4, and 5 have been determined by single-crystal X-ray diffraction.

Synthesis, characterization, alkaline phosphatase inhibition assay and molecular modeling studies of 1-benzylidene-2-(4-tert- butylthiazol-2-yl) hydrazines

Alkaline phosphatases are homodimeric protein enzymes which removes phosphates from several types of molecules. These catalyze the hydrolysis of monoesters in phosphoric acid which in turn catalyze a transphosphorylation reaction. Thiazoles are a privileged class of heterocyclic compounds which may potentially serve as effective phosphatase inhibitors. In this regard, the present research paper reports the facile synthesis and characterization of substituted 1-benzylidene-2-(4-tert-butylthiazol-2-yl) hydrazines with excellent yields. The synthesized compounds were tested for inhibitory potential against alkaline phosphatases. The compound 1-(4-Hydroxy, 3-methoxybenzylidene)-2-(4-tert-butylthiazol-2-yl) hydrazine (5e) was found to be the most potent inhibitor of human tissue non-alkaline phosphatase in this group of molecules with an IC50 value of 1.09 ± 0.18 μM. The compound 1-(3,4-dimethoxybenzylidene)-2-(4-tert-butylthiazol-2-yl) hydrazine (5d) exhibited selectivity and potency for human intestinal alkaline phosphatase with an IC50 value of 0.71 ± 0.02 μM. In addition, structure activity relationship and molecular docking studies were performed to evaluate their binding modes with the target site of alkaline phosphatase. The docking analysis revealed that the most active inhibitors showed the important interactions within the binding pockets of human intestinal alkaline phosphatase and human tissue non-alkaline phosphatase and may be responsible for the inhibitory activity of the compound towards the enzymes. Therefore, the screened thiazole derivatives provided an outstanding platform for further development of alkaline phosphatase inhibitors.

Effect directed synthesis of a new tyrosinase inhibitor with anti-browning activity

The inhibition of enzymatic browning is an attractive target to elevate the quality of foods. The objective of this work is to describe a novel platform for the discovery of tyrosinase inhibitors, based on (a) one-pot preparation of a library of thiosemicarbazide compounds, (b) biological evaluation using tyrosinase TLC bioautography, (c) inhibitor identification via mass spectrometry coupled to bioautography. During these proof-of-concept experiments, the approach led to the straightforward identification of a new thiosemicarbazone with improved tyrosinase inhibition properties and fresh-cut apple slices antibrowning effect when compared to kojic acid. In conclusion, the platform represents an interesting strategy for the discovery of this type of inhibitors.

Facile synthesis of novel fluorescent thiazole coumarinyl compounds: Electrochemical, time resolve fluorescence, and solvatochromic study

In this study, Benzocoumarin-Thiazoles-Azomethine derivatives with bioactive scaffolds were synthesized and characterized. The present investigation is concerned with the multistep synthesis of thiazole coumarinyl derivatives (5a-k), which were accomplished from naphthaldehyde, ethyl acetoacetate, and thiosemicarbazide. The formation of newly synthesized derivatives was confirmed by 1H NMR and 13C NMR spectroscopic studies. Thiazole coumarinyl derivatives were subjected to UV-Visible studies in different solvents such as ethanol, ethyl acetate, and DMF for solvatochromic studies. The synthesized coumarinyl thiazole compounds showed absorption in the range of 332-390 nm. Electrochemical studies were performed in DMSO and redox behavior was offered by thiazoles. Fluorescence of coumarinyl thiazole compounds were examined in ethanol, ethyl acetate, and DMF to visualize the solvent effect on the emitting ability of compounds. Fluorescence spectra of coumarinyl thiazoles expressed a sharp emission in the range 436-550 nm.

Thiosemicarbazones exhibit inhibitory efficacy against New Delhi metallo-β-lactamase-1 (NDM-1)

The superbug infection caused by metallo-β-lactamases (MβLs) carrying drug-resistant bacteria, specifically, New Delhi metallo-β-lactamase (NDM-1) has become an emerging threat. In an effort to develop novel inhibitors of NDM-1, thirteen thiosemicarbazones (1a-1m) were synthesized and assayed. The obtained molecules specifically inhibited NDM-1, with an IC50 in the range of 0.88–20.2 μM, and 1a and 1f were found to be the potent inhibitors (IC50 = 1.79 and 0.88 μM) using cefazolin as substrate. ITC and kinetic assays indicated that 1a irreversibly and non-competitively inhibited NDM-1 in vitro. Importantly, MIC assays revealed that these molecules by themselves can sterilize NDM-producing clinical isolates EC01 and EC08, exhibited 78-312-fold stronger activities than the cefazolin. MIC assays suggest that 1a (16 μg ml?1) has synergistic antimicrobial effect with ampicillin, cefazolin and meropenem on E. coli producing NDM-1, resulting in MICs of 4-32-, 4-32-, and 4-8-fold decrease, respectively. These studies indicate that the thiosemicarbazide is a valuable scaffold for the development of inhibitors of NDM-1 and NDM-1 carrying drug-resistant bacteria.

Copper compound taking 2-thiophenecarboxaldehyde thiosemicarbazone as ligand and synthesis method of copper compound

The invention discloses a copper compound taking 2-thiophenecarboxaldehyde thiosemicarbazone as a ligand and a synthesis method of the copper compound. The synthesis method comprises the following steps: adding thiosemicarbazone into absolute ethyl alcohol, performing stirring and dissolution, adding 2-thiophenecarboxaldehyde, performing uniform mixing, stirring the mixed solution at 70 DEG C in awater bath, performing volatilization at room temperature, separating a crystal so as to obtain a ligand; and adding the prepared ligand into absolute ethyl alcohol, performing stirring and dissolving, adding CuBr2.2H2O after dissolution, performing stirring at 70 DEG C in a water bath, performing volatilization at room temperature, and separating out a crystal, so as to obtain a Cu compound of the ligand. An in-vitro proliferation inhibition activity experiment is further carried out on the synthesized copper compound, results show that the synthesized series of copper compounds have generally good in-vitro activity, particularly have high specificity on human T24 and HeLa cells, show good inhibitory activity, have little toxic effect on human normal cells, and are suitable for preparingefficient and low-toxicity anti-tumor drugs.

Design, synthesis, biological evaluation, QSAR analysis and molecular modelling of new thiazol-benzimidazoles as EGFR inhibitors

Heterocyclic rings such as thiazole and benzimidazole are considered as privileged structures, since they constitute several FDA-approved drugs for cancer treatment. In this work, a new set of 2-(2-(substituted) hydrazinyl)-4-(1-methyl-1H-benzo[d]imidazol-2-yl) thiazoles 4a-q were designed as epidermal growth factor receptor (EGFR) inhibitors and synthesized using concise synthetic methods. The new target compounds have been evaluated in vitro for their suppression activity against EGFR TK. Compounds 4n, 4h, 4i, 4a and 4d exhibited significant potency in comparison with erlotinib which served as a reference drug (IC50, 71.67–152.59 nM; IC50 erlotinib, 152.59 nM). Furthermore, MTT assay revealed that compounds 4j, 4a, 4f, 4h, 4n produced the most promising cytotoxic potency against the human breast cancer cell line (MCF-7) (IC50; 5.96–11.91 μM; IC50 erlotinib; 4.15 μM). Compound 4a showed promising activity as EGFR TK inhibitor as well as anti-breast cancer agent. In addition, 4a induced apoptotic effect and cell cycle arrest at G2/M phase preventing the mitotic cycle in MCF-7 cells. Moreover, 4a upregulated the oncogenic parameters; caspase-3, p53, Bax/Bcl-2 as well as it inhibited the level of PARP-1 enzyme. QSAR study was carried out for the new derivatives and it revealed the goodness of the models. Furthermore, molecular docking studies represented the binding modes of the promising compounds in the active pocket of EGFR.

New hydrazinothiazole derivatives of usnic acid as potent TDP1 inhibitors

Tyrosyl-DNA phosphodiesterase 1 (Tdp1) is a promising therapeutic target in cancer therapy. Combination chemotherapy using Tdp1 inhibitors as a component can potentially improve therapeutic response to many chemotherapeutic regimes. A new set of usnic acid derivatives with hydrazonothiazole pharmacophore moieties were synthesized and evaluated as Tdp1 inhibitors. Most of these compounds were found to be potent inhibitors with IC50 values in the low nanomolar range. The activity of the compounds was verified by binding experiments and supported by molecular modeling. The ability of the most effective inhibitors, used at non-toxic concentrations, to sensitize tumors to the anticancer drug topotecan was also demonstrated. The order of administration of the inhibitor and topotecan on their synergistic effect was studied, suggesting that prior or simultaneous introduction of the inhibitor with topotecan is the most effective.