5351-80-4

Usage

Also known as

ethylidenehydrazinecarbothioamide

Properties

Potent inhibitor of tumor necrosis factor alpha (TNF-α), potential anti-inflammatory and anti-cancer properties

Specific content

Considered a potential therapeutic agent for the treatment of inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease

Significance

Target for further research and development in the field of medicinal chemistry due to its unique structure and mechanism of action

Upstream product

• 79-19-6 thiosemicarbazide 
• 99-93-4 4-Hydroxyacetophenone 

Downstream Products

• 69170-41-8 1-(4-hydroxy-phenyl)-ethanone [4-(1-methyl-1H-benzoimidazol-2-yl)-thiazol-2-yl]-hydrazone 
• 99-93-4 4-Hydroxyacetophenone 
• 144305-98-6 Mn(C₆H₄(OH)C(CH₃)NNHC(S)NH₂)2Cl₂ 

Relevant academic research and scientific papers

Combined theoretical and experimental studies reveal the newly synthesized pyrimidinones as potential apoptotic agents

Reaction of acetophenone thiosemicarbazones (5–8) and (2-methyl) diethyl malonate in absolute ethanol under reflux conditions furnished the corresponding pyrimidinone analogs (9–12) in good to excellent yields. The resulting pyrimidines were characterised

In vitro evaluation of new 4-thiazolidinones on invasion and growth of Toxoplasma gondii

Treatments for toxoplasmosis such as pyrimethamine have shown numerous side effects. It has been reported that the likelihood of relapse associated with pyrimethamine-based therapy in patients with HIV and toxoplasmic encephalitis (TE) can have significant implications, even for patients who often develop new lesions in areas of the brain previously free of infection. This led us to research for new agents against Toxoplasma gondii. Recent findings have shown the potent biological activity of 4-thiazolidinones. We proposed to design and synthesize a new series of 2-hydrazono-4-thiazolidinones derivatives to evaluate the in vitro growth inhibition effect on T. gondii. The growth rates of T. gondii tachyzoites in Human Foreskin Fibroblast (HFF) cell culture were identified by two in vitro methodologies. The first one was by fluorescence in which green fluorescent RH parasites and cherry-red fluorescent ME49 parasites were used. The second one was a colorimetric methodology using β-Gal parasites of the RH strain constitutively expressing the enzyme beta-galactosidase. The 4-thiazolidinone derivatives 1B, 2B and 3B showed growth inhibition at the same level of Pyrimethamine. These compounds showed IC50 values of 1B (0.468–0.952 μM), 2B (0.204–0.349 μM) and 3B (0.661–1.015 μM) against T. gondii. As a measure of cytotoxicity the compounds showed a TD50 values of: 1B (60 μM), 2B (206 μM) and 3B (125 μM). The in vitro assays and molecular modeling results suggest that these compounds could act as possible inhibitors of the Calcium-Dependent Protein Kinase 1 of T. gondii. Further, our results support the fact that of combining appropriate detection technologies, combinatorial chemistry and computational biology is a good strategy for efficient drug discovery. These compounds merit in vivo analysis for anti-parasitic drug detection.

Microwave-assisted synthesis and biological evaluation of new thiazolylhydrazone derivatives as tyrosinase inhibitors and antioxidants

In this work, we have synthesized a series of 2-thiazolylhydrazone derivatives (1–27) and investigated their biological activities as tyrosinase inhibitors and antioxidants. Some compounds showed potent tyrosinase inhibitory activities and 4-(2-(2-(1-(4-Aminophenyl)ethylidene)-hydrazinyl)thiazol-4-yl) phenol (26) showed more potent inhibitory effect than the standard tyrosinase inhibitor kojic acid (IC50: 9.8 μM vs. 23.6 μM). Compounds 2, 14, and 26 exhibited high antioxidant activities in 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. The structure–activity relationship (SAR) indicated that the substitutions of bromine, hydroxyl group, and amino groups cause great effect to the inhibition effect against tyrosinase. The mechanism and kinetic studies demonstrated that the inhibitory effect of compound 26 on the tyrosinase by acting as the reversible and uncompetitive inhibitor. Docking studies suggests that compound 26 interacts strongly with mushroom tyrosinase via hydrogen bonding.

Design, synthesis, bioactivity, and DFT calculation of 2-thiazolyl-hydrazone derivatives as influenza neuraminidase inhibitors

Three series of thiazolylhydrazone derivatives were designed, synthesized, and evaluated for their neuraminidase (NA) inhibitory activity against influenza virus H1N1 in vitro. Compounds 1 and 2 were synthesized via the one-pot reaction and compound 3 was

(4-alkyl-5-acyl-2-thiazole) hydrazone derivatives and medical application thereof

The invention relates to (4-alkyl-5-acyl-2-thiazole) hydrazone derivatives shown as a formula I and pharmaceutically acceptable salts thereof, a medicinal composition and the application thereof to preparation of an influenza virus neuraminidase inhibitor

Synthesis and antimicrobial properties of some new thiazolyl coumarin derivatives

Two novel series of hydrazinyl thiazolyl coumarin derivatives have been synthesized and fully characterized by IR, 1H NMR, 13C NMR, elemental analysis and mass spectral data. The structures of some compounds were further confirmed by X-ray crystallography. All of these derivatives, 10a-d and 15a-h, were screened in vitro for antimicrobial activity against various bacteria species including Mycobacterium tuberculosis and Candida albicans. The compounds 10c, 10d and 15e exhibited very good activities against all of the tested microbial strains.

Ruthenium(II) mediated C-H activation of substituted acetophenone thiosemicarbazones: Synthesis, structural characterization, luminescence and electrochemical properties

Treatment of [RuHCl(CO)(AsPh3)3] with 4′-substituted acetophenone thiosemicarbazone derivatives in methanol under reflux afford a series of air stable new ruthenium(II) cyclometalated complexes containing thiosemicarbazone of general

1-(1-Arylethylidene)thiosemicarbazide derivatives: A new class of tyrosinase inhibitors

A series of 1-(1-arylethylidene)thiosemicarbazide compounds and their analogues were synthesized and characterized by 1H NMR, MS. Their tyrosinase inhibitory activities were investigated by an assay based on the catalyzing ability of tyrosinase

M-STAGE KINESIN INHIBITOR

A mitotic kinesin Eg5 inhibitor which comprises a thiadiazoline derivative represented by the general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient: [wherein R1 represents a hydrogen atom and the like, R2 represents a hydrogen atom, -C(=W)R6 (wherein W represents an oxygen atom or a sulfur atom, and R6 represents substituted or unsubstituted lower alkyl and the like) and the like, R3 represents -C(=Z)R19 (wherein Z represents an oxygen atom or a sulfur atom, and R19 represents substituted or unsubstituted lower alkyl and the like) and the like, R4 represents substituted or unsubstituted lower alkyl and the like, and R5 represents substituted or unsubstituted aryl and the like] and the like are provided.

THIADIAZOLINE DERIVATIVE

(wherein R1 and R4 are the same or different and each represents a hydrogen atom, substituted or unsubstituted lower alkyl, substituted or unsubstituted lower alkynyl, substituted or unsubstituted lower alkenyl, or the like; R5 represents a substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl, or the like; R2 represents -C(-W)R6 or the like; R3 represents a hydrogen atom, -C(=WA)R6A, or the like) Antitumor agents which comprises a thiadiazoline derivative represented by the aforementioned general formula (I) or a pharmacologically acceptable salt thereof as an active ingredient are provided.