5351-60-0

Usage

Chemical structure

Thiourea derivative containing an amino group and a nitrophenyl group

Potential applications

a. Pharmaceuticals
b. Agrochemicals
c. Materials science

Biological activities

a. Anti-tumor properties
b. Anti-inflammatory properties

Use in coordination chemistry

Can be used as a ligand in metal complexation studies

Research interest

Due to its synthesis, properties, and potential applications, it is a compound of interest for further research and potential use in various industries.

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 2231-57-4 Thiocarbohydrazide 

Downstream Products

• 1452579-94-0 C₁₆H₁₂N₆O₃S 
• 1132880-99-9 4-nitrobenzaldehyde N'-(5-benzoylmethyl-1,3,4-thiadiazol-2-yl)hydrazone hydrobromide 

Relevant academic research and scientific papers

Synthesis of new deoxycholic acid bis thiocarbazones under solvent-free conditions using microwave irradiation

A simple method for the synthesis of new deoxycholic acid bis thiocarbazones under solvent-free conditions using microwave irradiation has been developed. Its main advantages are short reaction times, good conversions and the environmentally friendly nature of the process. Their structures were characterised by 1H NMR, IR, ESI-MS spectra and elemental analysis. The preliminary results indicate that some of these compounds possess inhibitory effects against Escherichia coli.

Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives

Derivatives of thiocarbohydrazone studied so far have shown great biological activity such as antioxidant, antimicrobial, and anticancer. Most of these compounds are bis-substituted derivatives, while monothiocarbohydrazones are much less investigated. Еighteen monothiocarbohydrazones were synthesized and subjected to physicochemical characterization in order to facilitate the examination of their potential biological activity and application in future studies. The structure of synthesized derivatives was confirmed with NMR and FT–IR spectroscopy, and with elemental analysis. For one of the compounds, single-crystal X-ray diffraction analysis was performed. Specific and non-specific molecular interactions were interpreted by LSER principles, using Catalan’s model. For additional information about the dominance and influence of the interactions presented, correlations with Hansen’s solubility parameters were calculated. Influence of the type and position of the substituent on absorption maxima was determined with LFER (linear free-energy relationship) principles, using Hammett’s equation. Acidity constants of the synthesized compounds were theoretically calculated and experimentally determined. Moreover, the excitation of a molecule by a photon of UV–Vis light was interpreted by time-dependent density functional theory (TD–DFT) calculations of UV absorption bands, and intramolecular charge transfer (ICT) was quantified by calculations of the charge transfer distances (DCT).

Synthesis of thiocarbohydrazide and carbohydrazide derivatives as possible biologically active agents

A series of new β-isatin aldehyde-N,N′-thiocarbohydrazone, bis-β-isatin thiocarbohydrazones, bis-β-isatin carbohydrazones was synthesized by condensation of 5-substituted isatin with thiocarbohydrazide or carbohydrazide. The chemical structures of the newly synthesized compounds were confirmed by FT-IR, 1H NMR, and mass spectral analysis. The synthesized compounds were evaluated for in vitro antiviral activity against various strains of DNA and RNA viruses, but exhibited moderate antiviral activity compared with the reference compounds. Among all the compounds 6c exhibited the highest chemoprevention activity in a two-stage mouse-skin carcinogenesis test. Graphical abstract: [Figure not available: see fulltext.]

Solvent-free synthesis of novel unsymmetric chenodeoxycholic acid bis thiocarbazone derivatives promoted by microwave irradiation and evaluation of their antibacterial activity

Eleven new non-symmetric chenodeoxycholic acid bis thiocarbazones were efficiently synthesized via the condensation of steroidal diketones (methyl (5β)-3,7-dioxocholan-24-oate) and substituted benzaldehyde thiocarbohydrazones by means of microwave irradiation. Compared with the conventional heating method, the yields were increased from 31-58% to 80-89% and the reaction times were reduced from 420-520 min to 5.0-7.5 min. The structures of these novel compounds were characterized by spectral data and elemental analysis. Four compounds (7a, 7c, 7f and 7g) possess excellent activity against Bacillus subtilis and Staphylococcus aureus.

Microwave assisted synthesis, characterization of some new isatin and thiophene derivatives as cytotoxic and chemopreventive agents

In obtaining some new cytotoxic and chemopreventive agents with potent antiproliferative activity against cancer cells, a series of new β-isatin aldehyde-N,N′-thiocarbohydrazone, bis-β-isatin thiocarbohydrazones, bis-β-isatin carbohydrazones, N,2-bis(thiophen-2-ylmethylidene) thiocarbohydrazone and N,2-bis(thiophen-2-ylmethylidene) carbohydrazone derivatives was synthesized by microwave oriented reaction and evaluated for their in vitro cytotoxic activity. The newly synthesized compounds were characterized based on spectral (FT-IR, NMR, MS) analyses. The inhibitory effects of synthesized compounds on the proliferation of murine leukemia cells (L1210), human T-lymphocyte cells (CEM) and human cervix carcinoma cells (HeLa) were assayed by using MTT assay. The compounds were also tested for their inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-Otetradecanoylphorbol-13-acetate (TPA). In vitro evaluation of these schiff bases revealed mild to moderate cytotoxic activity in a dose dependent manner. The results of the in vitro inhibitory activities of synthetic compounds against EBVEA activation with IC50 ranges from 485-535 (mol ratio/32pmol/TPA). Chlorine group containing derivatives did not show increased inhibitory activity against tumor promoter TPA induction. Sulphur containing derivatives also did not show a high inhibitory potency in this system.

Synthesis of new ferrocene bis thiocarbazones under solvent-free conditions using microwave

A simple efficient method for the synthesis of new ferrocene bis thiocarbazones via microwave irradiation under solvent-free conditions has been developed. Compared to the conventional method, its major advantages are short reaction times, good conversions and actually accorded the green synthesis technology. The structures of target compounds were confirmed by 1H NMR, IR, ESI-MS spectra data and elemental analysis. Preliminary bioassay results showed that some of these compounds possess inhibitory effects against S. aureus, S. pyogenes and E. coli bacteria.

RING-CHAIN AND RING-LINEAR-RING TAUTOMERISM IN THIOCARBONOHYDRAZONES

The structure of the thiocarbonohydrazones of monocarbonyl compounds was studied by 1H and 13C NMR spectroscopy in solutions and by mass spectrometry in the gas phase. In solutions, irrespective of the substitution in the aromatic ring and in the hydrazine fragment, the thiocarbonohydrazones of aromatic aldehydes exist in the linear form, whereas the 2- and 5-substituted thiocarbonohydrazones of ketones are susceptible to ring-chain tautomerism: Thiocarbonohydrazone - 4-amino-1,2,4-triazolidine-3-thione. Those not having substituents at the nitrogen atoms are susceptible to ring-linear-ring equilibria: Hexahydro-1,2,4,5-tetrazine-3-thione - thiocarbonohydrazone - 4-amino-1,2,4-triazolidine-3-thione. In the gas phase under conditions of high vacuum, according to the mass spectra, the coexistence of four tautomeric forms (linear, tetrazine, triazolidine, and 2-hydrazino-1,3,4-thiadiazolidine) is possible in individual cases.