70619-48-6

Usage

Uses

Used in Pharmaceutical Industry:
4-(3-Fluorophenyl)-3-thiosemicarbazide is used as a chemical intermediate for the development of new drugs, leveraging its potential antimicrobial, antifungal, and antitumor properties. Its structural features contribute to its favorable pharmacokinetic and pharmacodynamic properties, enhancing its potential as a candidate for further research and development in drug discovery and design.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4-(3-fluorophenyl)-3-thiosemicarbazide serves as a valuable compound for studying the structure-activity relationships of thiosemicarbazide derivatives. Its unique molecular structure allows researchers to explore its interactions with biological targets and evaluate its potential as a lead compound for the development of novel therapeutic agents.
Used in Antimicrobial Agents:
4-(3-Fluorophenyl)-3-thiosemicarbazide is utilized as an antimicrobial agent, exhibiting activity against various types of bacteria and fungi. Its ability to inhibit microbial growth makes it a potential candidate for the development of new antibiotics and antifungal drugs, addressing the growing need for effective treatments against drug-resistant pathogens.
Used in Antitumor Therapy:
As an antitumor agent, 4-(3-fluorophenyl)-3-thiosemicarbazide may have the potential to target and inhibit the growth of cancer cells. Its incorporation into cancer therapeutics could provide a novel approach to treating various types of tumors, offering new hope for patients with limited treatment options.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic efficacy of 4-(3-fluorophenyl)-3-thiosemicarbazide, it can be incorporated into drug delivery systems. These systems, which may include organic and metallic nanoparticles, can improve the compound's delivery to target sites, increasing its effectiveness and reducing potential side effects.

InChI:InChI=1/C7H8FN3S/c8-5-2-1-3-6(4-5)10-7(12)11-9/h1-4H,9H2,(H2,10,11,12)

Upstream product

• 1313419-78-1 C₉H₇FNO₂S₂^(1-)*Na⁽¹⁺⁾ 
• 372-19-0 meta-fluoroaniline 
• 76874-99-2 C₇H₆FNS₂ 
• 404-72-8 3-fluorophenyl isothiocyanate 
• 75-15-0 carbon disulfide 

Downstream Products

• 16113-65-8 benzaldehyde [3-(3-fluoro-phenyl)-4-oxo-5-phenyl-thiazolidin-2-ylidene]-hydrazone 
• 16113-62-5 benzaldehyde [3-(3-fluoro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 16113-63-6 benzaldehyde [3-(3-fluoro-phenyl)-5-methyl-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 16113-64-7 benzaldehyde [5-ethyl-3-(3-fluoro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 70618-03-0 2-acetylpyridine 4-(3-fluorophenyl)-3-thiosemicarbazone 
• 1221255-86-2 N-(3-fluorophenyl)-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide 
• 1282612-23-0 C₃₉H₅₀F₂N₆O₂S₂ 
• 1332478-52-0 methyl (5β)-3-[2-[[(3-fluorophenyl)amino]thioxomethyl]hydrazinylidene]-12-oxocholan-24-oate 
• 1410795-81-1 methyl (5β)-3,7-bis[2-[[(3-fluorophenyl)amino]thioxomethyl]hydrazinylidene]-cholan-24-oate 
• 1353899-39-4 N⁽³⁾-meta-fluorophenyl-acetophenone-thiosemicarbazone 
• 891553-77-8 N⁽³⁾-meta-fluorophenyl-benzophenone-thiosemicarbazone 
• 1332336-83-0 N-(3-fluorophenyl)-2-[2-oxo-5-(trifluoromethoxy)-1,2-dihydro-3H-indol-3-ylidene]-1-hydrazinecarbothioamide 
• 16113-41-0 benzaldehyde 4-(3-fluoro-phenyl)-thiosemicarbazone 

Relevant academic research and scientific papers

Synthesis and antibacterial activity of novel Schiff bases of thiosemicarbazone derivatives with adamantane moiety

Increased bacterial resistance to antibiotics is a major threat to human health, and it is particularly important to develop novel antibiotic drugs. Here, we designed a series of Schiff base thiosemicarbazone derivatives containing an adamantane moiety, and carried out the structural characterization of the compounds and in vitro antibacterial activity tests. Compound 7e was as effective as the commonly used antibiotic ampicillin against the Gram-negative bacterium Escherichia coli, and compound 7g had a good inhibitory effect against Gram-positive Bacillus subtilis. These findings provide data for the development of better thiosemicarbazone antibacterial agents.

Preparation and application of thiosemicarbazone compound

The invention discloses a thiosemicarbazone compound, and biological activity analysis is carried out on the thiosemicarbazone compound. The invention also discloses application of the thiosemicarbazone compound in preparation of antibacterial drugs. According to the invention, important intermediates 6a-6h are synthesized from hydrazine hydrate and react with adamantane benzaldehyde respectivelyto synthesize eight adamantane aromatic aldehyde thiosemicarbazone compounds, the structures of the compounds can be confirmed by infrared, nuclear magnetic hydrogen spectrum, carbon spectrum and massspectrum methods, and the antibacterial activity of the compounds is tested in vitro. The result shows that the compound has a good antibacterial effect on escherichia coli and bacillus subtilis.

Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety

A series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5 ± 0.4% and 95.7 ± 1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3 ± 2.2% and 92.3 ± 0.6% at a concentration of 10 μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5 m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells.

Synthesis, characterization, and antioxidant activity of some new N 4-arylsubstituted-5-methoxyisatin-β-thiosemicarbazone derivatives

Abstract: Firstly, thiosemicarbazides were prepared by the reaction of hydrazine monohydrate with isothiocyanates in cold dry ethanol at 0?°C for 1?h. After that, new isatin-β-thiosemicarbazones were synthesized by treatment of 5-methoxyisatin with thiose

Novel Schiff bases derived from isothiocyanates: synthesis, characterization, and antioxidant activity

A series of novel thiosemicarbazones including Schiff bases were synthesized by treatment of various aryl-substituted aldehydes with thiosemicarbazides in ethanol containing one drop of hydrochloric acid at reflux for 3–5 h. For this, thiosemicarbazides were obtained from hydrazine monohydrate and isothiocyanates in cold dry ethanol at 0 °C for 1 h. FT-IR, 1H NMR, 13C NMR, and LC–MS/MS spectroscopic methods and elemental analysis were used to characterize the identification of the synthesized products. The in vitro antioxidant activity of these compounds was tested by the 1,1-diphenyl-2-picryl hydrazyl (DPPH) free radical trapping method. All of the synthesized compounds showed lower antioxidant activity than the ascorbic acid standard and followed the sequence I > VII > X > VI > IV > IX > XI > II > V > III > VIII.

Synthesis, molecular modeling and antiviral activity of novel 5-fluoro-1H-indole-2,3-dione 3-thiosemicarbazones

In this work, novel 5-fluoro-1-methyl/ethyl-1H-indole-2,3-dione 3-[4-(substituted phenyl)-thiosemicarbazones] 6a-n and 7a-n were synthesized. The antiviral effects of the compounds were tested against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV in HEL cell cultures using acyclovir and ganciclovir as standards, and Coxsackie B4 virus in Vero cell cultures using ribavirin and mycophenolic acid as standards. R2 ethyl substituted 7 derivatives were found effective against viruses tested. R1 4-CF3 substituted 7d, R1 4-OCH3 substituted 7 g and R1 3-Cl substituted 7 l showed activity against HSV-1 (KOS), HSV-2 (G) HSV-1 TK- KOS ACVr and VV. Whereas only R1 4-Br substituted 7n has selective activity against coxsackie B4 virus. Molecular modeling studies of 7d and 7l were performed to determine binding side on HSV-1 glycoprotein B and D, HSV-2 glycoprotein B structures.

Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives

Schiff-base–bearing new bis(thiosemicarbazone) derivatives were prepared from terephthalaldehyde and various thiosemicarbazides. FT–IR, 1 H NMR, 13 C NMR, and UV–Vis spectroscopic methods and elemental analysis were used to elucidate

Novel selective thiadiazine DYRK1A inhibitor lead scaffold with human pancreatic β-cell proliferation activity

The Dual-Specificity Tyrosine Phosphorylation-Regulated Kinase 1A (DYRK1A) is an enzyme that has been implicated as an important drug target in various therapeutic areas, including neurological disorders (Down syndrome, Alzheimer's disease), oncology, and

Thiosemicarbazide, a fragment with promising indolamine-2,3-dioxygenase (IDO) inhibition properties

With the aim to explore the interest of the thiosemicarbazide scaffold for the inhibition of the indoleamine 2,3-dioxygenase (IDO), a promising therapeutic target for anticancer immunotherapy, a series of 32 phenylthiosemicarbazide derivatives was prepared and their IDO inhibition evaluated. Our study demonstrated that among these derivatives, compound 14 characterized with a 4-cyanophenyl group on the thiosemicarbazide was the more potent IDO inhibitor in this series being endowed with an IC50 of 1.2 μM. The SAR depicted showed that substitution in the 3- and 4-position relative to the phenylthiosemicarbazide are very promising whereas substitution in the 2-position always leads to less potent or inactive derivatives. In fact the study highlighted a novel interesting scaffold for IDO inhibition for further development.

Structural studies on acetophenone- and benzophenone-derived thiosemicarbazones and their zinc(II) complexes

In the present work N(3)-meta-chlorophenyl-(HAc3mCl, 1) and N(3)-meta-fluorphenyl-(HAc3mF, 2) acetophenone thiosemicarbazone, and N(3)-meta-chlorophenyl-(HBz3mCl, 3) and N(3)-meta-fluorphenyl-(HBz3mF, 4) benzophenone thiosemicarbazone were obtained, as we