5470-48-4

Basic information

• Product Name: [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol
• Synonyms: [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol;1-(4-Nitrobenzylidene)thiosemicarbazide;4-Nitrobenzaldehydethiosemicarbazone;p-Nitrobenzaldehyde thiosemicarbazone
• CAS NO: 5470-48-4
• Molecular Formula: C₈H₈N₄O₂S
• Molecular Weight: 224.24
• Mol File: 5470-48-4.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 405.6°C at 760 mmHg
• Flash Point: 199.1°C
• Appearance: /
• Density: 1.46g/cm³
• Vapor Pressure: 8.65E-07mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol(CAS DataBase Reference)
• NIST Chemistry Reference: [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol(5470-48-4)
• EPA Substance Registry System: [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol(5470-48-4)

Safety Data

• Hazardous Substances Data: 5470-48-4(Hazardous Substances Data)

Usage

Description

[2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol is a complex organic compound characterized by the presence of a nitrobenzylidene group, a hydrazono group, an amino group, and a thiol group. [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol is known for its potential biological activity and is often utilized in pharmaceutical and research applications. The combination of the nitro group and the thiol group suggests that it may possess antioxidant and antibacterial properties, while the presence of the amino group indicates the potential for binding and interactions with biological molecules. [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol's diverse functional groups contribute to its chemical interest and possible biological relevance.

Uses

Used in Pharmaceutical Applications:
[2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol is used as a pharmaceutical agent for its potential antioxidant and antibacterial properties. The presence of the nitro group and the thiol group allows the compound to exhibit these characteristics, making it a candidate for the development of new drugs targeting various diseases and infections.
Used in Research Applications:
In the field of research, [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol is used as a chemical probe for studying the interactions between biological molecules and its constituent functional groups. The amino group's ability to bind with other molecules makes it a valuable tool for investigating various biological processes and mechanisms.
Used in Antioxidant Development:
[2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol is used as a precursor in the development of novel antioxidants. Its nitro and thiol groups contribute to its potential antioxidant properties, which can be harnessed to create new compounds with enhanced antioxidant capabilities.
Used in Antibacterial Agents:
[2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol is utilized as a starting material in the synthesis of new antibacterial agents. [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol's structure allows for modifications and improvements to create more effective and targeted treatments against bacterial infections.
Used in Chemical Synthesis:
In the chemical industry, [2-(4-Nitrobenzylidene)hydrazono](amino)methanethiol serves as an intermediate in the synthesis of various complex organic compounds. Its unique structure and functional groups make it a versatile building block for creating a wide range of chemical products.

InChI:InChI=1/C8H8N4O2S/c9-8(15)11-10-5-6-1-3-7(4-2-6)12(13)14/h1-5H,(H3,9,11,15)/b10-5+

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 79-19-6 thiosemicarbazide 
• 4346-94-5 thiosemicarbazide hydrochloride 

Downstream Products

• 93691-33-9 (E)-2((E)-(4-nitrobenzylidene)hydrazono)thiazolidine-4-one 
• 132778-88-2 N,N'''-bis-(4-nitro-benzylidene)-μ-disulfido-dicarboxamidrazone 
• 4871-28-7 1-(4-nitrobenzylidene)-2-(4-(4-methoxyphenyl)thiazol-2-yl)-hydrazine 
• 117971-60-5 2-{[1-(4-Nitro-phenyl)-meth-(Z)-ylidene]-hydrazono}-2,3-dihydro-[1,3]thiazin-4-one 
• 877455-52-2 (RhCl(P(C₆H₅)3)2(NO₂C₆H₃CHNNC(NH₂)S)) 
• 1187878-79-0 [Ru(P(C₆H₅)3)2(CO)(H)(SC(NH₂)NNCHC₆H₄NO₂)] 
• 1187878-79-0 trans-[ruthenium(carbonyl)(hydride)(triphenylphosphine)2(SC(NH₂)N₂CHC₆H₄NO₂)] 
• 1338084-26-6 C₁₈H₁₇N₇O₅S 
• 1338083-71-8 C₁₃H₉N₇O₄S 
• 1338083-93-4 C₁₅H₁₂N₆O₄S 
• 1338084-05-1 C₁₃H₈N₆O₄S 

Relevant articles and documents

Synthesis, in vitro thymidine phosphorylase activity and molecular docking study of thiadiazole bearing isatin analogs

A series of seventeen analogs (1─17) were synthesized and characterized through different spectroscopic techniques such as 1H, 13CNMR, HR-EI-MS and were evaluated for in vitro thymidine phosphorylase inhibition. All compounds showed excellent to good thymidine phosphorylase activity having IC50 value ranging between 4.10 ± 0.20 and 54.60 ± 1.40?μM when compared with standard drug 7-deazaxanthine (IC50 = 38.68 ± 1.12?μM). Among the series, compounds 1 (IC50 = 8.30 ± 0.30?μM), 6 (IC50 = 6.30 ± 0.10?μM), 11 (IC50 = 8.40 ± 0.30?μM) and 16 (IC50 = 4.10 ± 0.20?μM) were found more potent. Potent compounds were further subjected to molecular docking study to identify their interactions with the active site of amino acid. Structure activity relationship was done for all analogs mostly based on substitution pattern on phenyl and isatin rings. Graphic abstract: [Figure not available: see fulltext.]

Assessment of Thiosemicarbazone-Containing Compounds as Potential Antileukemia Agents against P-gp Overexpressing Drug Resistant K562/A02 Cells

P-Glycoprotein (P-gp) overexpression is considered to be the leading cause of multidrug resistance (MDR) and failure of chemotherapy for leukemia. In this study, seventeen thiosemicarbazone-containing compounds were prepared and evaluated as potential ant

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.