2646-31-3

Usage

Uses

Used in Pharmaceutical Research:
4-(4-BROMOPHENYL)-3-THIOSEMICARBAZIDE is used as a research compound for its potential biological activities, including its antibacterial and antifungal properties. It is studied for its ability to combat various types of bacteria and fungi, which could lead to the development of new antimicrobial agents.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(4-BROMOPHENYL)-3-THIOSEMICARBAZIDE is used as a building block for the synthesis of other organic compounds. Its unique structure and reactivity make it a valuable component in the creation of new molecules with potential applications in various industries.
Used in Chemical Research:
4-(4-BROMOPHENYL)-3-THIOSEMICARBAZIDE is utilized in chemical research to explore its chemical properties and reactivity. Understanding these characteristics can contribute to the advancement of chemical science and the discovery of new applications for 4-(4-BROMOPHENYL)-3-THIOSEMICARBAZIDE.
Used in Material Science:
In material science, 4-(4-BROMOPHENYL)-3-THIOSEMICARBAZIDE may be used to develop new materials with specific properties. Its unique structure could contribute to the creation of materials with enhanced characteristics, such as improved stability or reactivity, for use in various applications.

InChI:InChI=1/C7H8BrN3S/c8-5-1-3-6(4-2-5)10-7(12)11-9/h1-4H,9H2,(H2,10,11,12)

Upstream product

• 1985-12-2 4-Bromophenyl isothiocyanate 
• 15964-00-8 (4-bromo-phenyl)-dithiocarbamic acid 
• 3926-62-3 sodium monochloroacetic acid 
• 106-40-1 4-bromo-aniline 
• 1313419-74-7 C₉H₇BrNO₂S₂^(1-)*Na⁽¹⁺⁾ 
• 75-15-0 carbon disulfide 
• 302-01-2 hydrazine 

Downstream Products

• 112298-89-2 1-(4-bromophenyl)-2-thiobiurea 
• 2209-68-9 hydrazine-N,N'-bis-carbothioic acid anilide-(4-bromo-anilide) 
• 90869-24-2 propionaldehyde-[4-(4-bromo-phenyl)-thiosemicarbazone] 
• 98434-40-3 (4-bromo-phenyl)-[1,3,4]thiadiazol-2-yl-amine 
• 14731-28-3 5-(4-bromo-anilino)-3H-[1,3,4]thiadiazole-2-thione 
• 68371-97-1 (4-bromo-phenyl)-[1,2,3,4]thiatriazol-5-yl-amine 
• 87200-43-9 N-(4-bromophenyl)-N'-<2-methyl-4(3H)-quinazolinon-3-yl> thiourea 
• 82236-72-4 C₁₆H₁₃BrN₄OS 
• 79560-77-3 C₁₆H₁₃BrN₄OS 
• 79560-82-0 C₂₁H₂₂BrN₅OS 
• 79560-87-5 C₂₀H₂₀BrN₅O₂S 
• 82236-87-1 C₂₂H₂₄BrN₅OS 
• 82236-82-6 C₂₁H₂₂BrN₅O₂S 
• 200349-23-1 Ru((C₅H₄N)2)2(BrC₆H₄NHC(S)NNH₂)⁽¹⁺⁾*ClO₄^(1-)=[Ru((C₅H₄N)2)2(BrC₆H₄NHC(S)NNH₂)]ClO₄ 

Relevant academic research and scientific papers

Synthesis, characterization, and X-ray crystal structures of copper(II) and nickel(II) complexes with two bis(thiosemicarbazone) ligands and investigation of their electrochemical behavior

Two new bis(thiosemicarbazone) ligands having a halogen substituent on the non-coordinating phenyl rings, namely 2-[1-(2-{3-[2-({2-[(4-bromoanilino)carbothioyl]hydrazono} methyl)phenoxy]propoxy}phenyl)methylidene]-N1-(4-bromophenyl)-1-hydrazinecarbothiami

Thiosemicarbazone-based lead optimization to discover high-efficiency and low-toxicity anti-gastric cancer agents

In this paper, a series of thiosemicarbazone derivatives containing different aromatic heterocyclic groups were synthesized and the tridentate donor system of the lead compound was optimized. Most of the target compounds showed improved antiproliferative activity against MGC803 cells. SAR studies revealed that compound 5d displayed significant advantages in inhibition effect with an IC50 value of 0.031 μM, and better selectivity between cancer and normal cells than 3-AP and DpC (about 15- and 5-fold improved respectively). Besides, compound 5d showed selective antiproliferative activity in not only other cancer cells but also different gastric cancer cell lines. In-depth mechanism studies showed that compound 5d could induce mitochondria-related apoptosis which might be related to the elevation of intracellular ROS level, and cause cell cycle arrest at S phase. Moreover, 5d could evidently suppress the cell migration and invasion by blocking the EMT (epithelial–mesenchymal transition) process. Consequently, our studies provided a lead optimization strategy of thiosemicarbazone derivatives which would contribute to discover high-efficiency and low-toxicity agents for the treatment of gastric cancer.

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.

Novel 4-quinoline-thiosemicarbazone derivatives: Synthesis, antiproliferative activity, in vitro and in silico biomacromolecule interaction studies and topoisomerase inhibition

Twelve 2-(quinolin-4-ylmethylene) hydrazinecarbothioamide derivatives were synthetized and their biological properties were investigated, among which, the ability to interact with DNA and BSA through UV–Vis absorption, fluorescence, Circular Dichroism, molecular docking and relative viscosity, antiproliferative activity against MCF-7 and T-47D mammary tumor cells and RAW-264.7 macrophages and inhibitory capacity of the enzyme topoisomerase IIα. In the binding study with DNA and BSA, all the compounds displayed affinity for interaction with both biomolecules, especially JF-92 (p-ethyl-substituted), with binding constant of 1.62 × 106 and 1.43 × 105, respectively, and DNA binding mode by intercalation. The IC50 values were obtained between 0.81 and 1.48 μM and topoisomerase inhibition results in 10 μM. Thus, we conclude that the reduction of the acridine to quinoline ring did not disrupt the antitumor action and that substitution patterns are important for biomolecule interaction affinity as they demonstrate the potential of these compounds for anticancer therapy.

Synthesis of thiophene-thiosemicarbazone derivatives and evaluation of their in vitro and in vivo antitumor activities

A series of thiophene-2-thiosemicarbazones derivatives (5-14) was synthesized, characterized and evaluated for their antitumor activity. They were tested in vitro against human tumor cell lines through the colorimetric method. The results revealed that compounds 7 and 9 were the most effective in inhibiting 50% of the cell growth after 48 h of treatment. As compound 7 showed a potent antiproliferative profile, it has been chosen for further studies in 786-0 cell line by flow cytometry. Treatments with compound 7 (50 μM) induced early phosphatidylserine exposure after 18 h of exposure and this process progressed phosphatidylserine exposure with loss of cell membrane integrity after 24 h of treatment, suggesting a time-dependent cell death process. Regarding the cell cycle profile, no changes were observed after treatment with compound 7 (25 μM), suggesting a mechanism of cell death independent on the cell cycle. The in vivo studies show that compound 7 possess low acute toxicity, being the doses of 30-300 mgKg-1 chosen for studies in Ehrlich solid tumor model in mice. All doses were able to inhibit tumor development being the lowest one the most effective. Our findings highlight thiophene-2-thiosemicarbazones as a promising class of compounds for further studies concerning new anticancer therapies.

Design, synthesis and biological evaluation of novel thiosemicarbazide analogues as potent anticonvulsant agents

Novel thiosemicarbazide derivatives were synthesised and evaluated for their anticonvulsant activity and neurotoxicity. Anticonvulsant activity was done for grand mal and petit mal types of epilepsies by maximal electroshock (MES) and pentylenetetrazol (P

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.

ARYL-AND HETEROARYL-SUBSTITUTED BENZENE DERIVATIVES AS MODULATORS OF PI3-KINASE SIGNALLING PATHWAYS

The present disclosure relates to certain aryl- or heteroaryl-substituted benzene derivatives, pharmaceutical compositions containing them, and methods of using them, including methods for modulating autophagy or preventing, reversing, slowing or inhibiting the PI3K-AKT-MTOR pathway, and methods of treating diseases that are associated with autophagy or the PI3K-AKT-MTOR pathway.

Design, synthesis and anticonvulsant evaluation of novel N-(4-substituted phenyl)-2-[4-(substituted) benzylidene]-hydrazinecarbothio amides

Thirty six new N-(4-substituted phenyl)-2-[4-(substituted) benzylidene]-hydrazinecarbothioamides were synthesized and evaluated for anticonvulsant activity and neurotoxicity. The anticonvulsant activity was established in three seizure models i.e. MES, scMET and 6 Hz model. The most active compound was 2-[4-(4-chlorophenoxy)benzylidene]-N-(4-fluorophenyl) hydrazinecarbothioamide PC 31 which showed 100% protection at 0.5 h in the 6 Hz test. Compound 2-[4-(4-bromophenoxy) benzylidene]-N-(4-bromophenyl) hydrazinecarbothioamide PC 23 was found to be active in both the MES and 6 Hz test. A computational study was carried out from calculation of a pharmacophore pattern and the prediction of pharmacokinetic properties. Titled compounds have also exhibited good binding properties with epilepsy molecular targets such as glutamate, GABA (A) delta and GABA (A) alpha-1 receptors, in the Lamarckian genetic algorithm based on flexible docking studies.

Isatin-β-thiosemicarbazones as potent herpes simplex virus inhibitors

A series of isatin-β-thiosemicarbazones have been designed and evaluated for antiviral activity against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in a plaque reduction assay. Their cytotoxicity was examined using human rhabdomyosarcoma cells (RD cells). Several derivatives of isatin-β-thiosemicarbazone exhibited significant and selective antiviral activity with low cytotoxicity. It was found that the thiourea group at thiosemicarbazone and the NH functionality at isatin were essential for their antiherpetic activity. The synthesis and structure-activity relationship studies are presented.