5706-78-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorobenzaldehyde thiosemicarbazone is used as a potential antitubercular drug for combating tuberculosis bacteria. Its chemical structure enables it to target and inhibit the growth of Mycobacterium tuberculosis, the bacterium responsible for causing tuberculosis. This application is particularly relevant in the context of increasing antibiotic resistance and the need for new, effective treatments against drug-resistant tuberculosis strains.

InChI:InChI=1/C8H8ClN3S/c9-7-4-2-1-3-6(7)5-11-12-8(10)13/h1-5H,(H3,10,12,13)/b11-5+

Upstream product

• 34025-59-7 2,4-bis(2-chlorophenyl)-3-azabicyclo<3.3.1>nonan-9-one 
• 79-19-6 thiosemicarbazide 
• 4346-94-5 thiosemicarbazide hydrochloride 
• 89-98-5 2-chloro-benzaldehyde 
• 2698-41-1 o-chlorobenzylidene malononitrile 

Downstream Products

• 109699-99-2 5-(4-methoxy-benzylidene)-thiazolidine-2,4-dione-2-(2-chloro-benzylidenehydrazone) 
• 109567-24-0 5-salicylidene-thiazolidine-2,4-dione-2-(2-chloro-benzylidenehydrazone) 
• 109690-15-5 2-chloro-benzaldehyde (5-butyl-4-oxo-thiazolidin-2-ylidene)-hydrazone 
• 137609-27-9 5-(2-Chloro-phenyl)-thiazolo[4,3-b][1,3,4]thiadiazol-2-ylamine 
• 137609-20-2 2-(2-Chloro-phenyl)-3-(5-oxo-2-thioxo-imidazolidin-1-yl)-thiazolidin-4-one 
• 137609-13-3 2-(2-Chloro-phenyl)-2'-imino-[3,3']bithiazolidinyl-4,4'-dione 
• 122386-04-3 Cu⁽¹⁺⁾*C₈H₇ClN₃S^(1-)={Cu(C₆H₄ClCHNNCSNH₂)} 
• 79188-60-6 Pd(o-chlorobenzalidenethiosemicarbazonate)2 
• 324066-82-2 N'-[4-(4-bromophenyl)thiazol-2-yl]-N-(2-chlorobenzylidene)hydrazine 
• 1338084-31-3 C₁₈H₁₇ClN₆O₃S 
• 1338083-76-3 C₁₃H₉ClN₆O₂S 
• 1338083-98-9 C₁₅H₁₂ClN₅O₂S 
• 1338084-10-8 C₁₃H₈ClN₅O₂S 
• 1018475-04-1 2-[{5-(2-chlorophenyl)-[1,3,4]-thiadiazol-2-yl}imino]-1,3-thiazolidin-4-one 

Relevant academic research and scientific papers

Inhibition kinetics of chlorobenzaldehyde thiosemicarbazones on mushroom tyrosinase

2-Chlorobenzaldehyde thiosemicarbazone (2-Cl-BT) and 4-chlorobenzaldehyde thiosemicarbazone (4-Cl-BT) were synthesized, and their inhibitory kinetics on the activity of mushroom tyrosinase were investigated. Results showed that these compounds exhibited s

Effect of organic solvents on solvatochromic, fluorescence, and electrochemical properties of synthesized thiazolylcoumarin derivatives

In this present investigation, thiazolylcoumarin derivatives (5a–5k) were synthesized from thiosemicarbazide, ethyl acetoacetate, and naphthaldehyde through a multistep route. The formation of thiazolylcoumarin derivatives with bioactive scaffolds was con

The design, synthesis, and: In vitro trypanocidal and leishmanicidal activities of 1,3-thiazole and 4-thiazolidinone ester derivatives

Chagas and leishmaniasis are both neglected tropical diseases, whose inefficient therapies have made them remain the cause for millions of deaths worldwide. Given this, we synthesized 27 novel 1,3-thiazoles and 4-thiazolidinones using bioisosteric and est

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.

Intrabacterial Metabolism Obscures the Successful Prediction of an InhA Inhibitor of Mycobacterium tuberculosis

Tuberculosis, caused by Mycobacterium tuberculosis (M. tuberculosis), kills 1.6 million people annually. To bridge the gap between structure- A nd cell-based drug discovery strategies, we are pioneering a computer-aided discovery paradigm that merges stru

Synthesis and comparison of antileishmanial and cytotoxic activities of S-(?)-limonene benzaldehyde thiosemicarbazones with their R-(+)-analogues

In this study, we explore a series of novel potential antiprotozoal S-(?)-limonene-based benzaldehyde thiosemicarbazones were synthesised and their activity effective against the extracellular promastigote form of Leishmania amazonensis examined. Likewise, in parallel, a series of R-(+)-limonene-based thiosemicarbazones previously synthesised by our research group and thiosemicarbazones lacking the monoterpenic moiety, were also biologically evaluated. Here, we report the combination of theoretical and experimental approaches, as well as statistical analysis, to investigate the effect of the monoterpenic group and its stereochemistry in the biological activity of benzaldehyde thiosemicarbazone derivatives, for the identification of their structure-activity relationship. The terpenic thiosemicarbazones displayed the highest activities, confirming that the monoterpenic moiety is essential for activity. Notably, among the compounds tested, the S-(?)-enantiomer of the 4-nitro-derivative (8d) presented considerably lower cytotoxicity than its R-(+)-analogue, emphasizing the importance of the stereochemistry. The most active derivative (8d) exhibited a potent antiprotozoal activity (IC50 2.4 μM) and high selectivity (SI > 1147). Also, theoretical calculations were carried out at the density functional theory (DFT) level to show that the Gibbs free energy and LUMO orbitals present an excellent correlation with the experimental IC50 values. Finally, the combination of all these results may in principle be extremely advantageous to a deeper chemical understanding, as well as, allows a rational alternative for the future development of new drugs that act against leishmaniasis.

Synthesis and evaluation of novel 1,3,4-thiadiazole–fluoroquinolone hybrids as antibacterial, antituberculosis, and anticancer agents

A series of 5-substituted-1,3,4-thiadiazole-based fluoroquinolone derivatives were designed as potential antibacterial and anticancer agents using a molecular hybridization approach. The target compounds 16–25 were synthesized by reacting the correspondin

Microwave Assisted Synthesis and Biological Activity of Novel Bis{2-[2-(substituted benzylidene)hydrazinyl]thiazole} Derivatives

Abstract—New 4,4'-(4,6-dimethoxy-1,3-phenylene)bis{2-[2-(substituted benzylidene)hydrazinyl]thiazole} derivatives (5a–5j) have been synthesized from the corresponding 1,1'-(4,6-dimethoxy-1,3-phenylene)bis(2,2- dibromoethanone) and substituted thiosemicarbazones by the conventional method and under microwave irradiation. Structures of the synthesized compounds were characterized by FT-IR, 1H, and 13C NMR and Mass spectra. The products were evaluated for their in vitro antibacterial activity against Gram-positive and Gramnegative stains. Some of the compounds 5b, 5f, 5h demonstrated high activity against B. subtilis (+ve), compound 5c exhibited high activity against E. coli (–ve) and P. aeruginosa (–ve) stains. Among the titled compounds also evaluated for their in vitro antimycobacterial activity, the product 5b demonstrated pronounced antimycobacterial activity against M. bovis stain.

One PotTwo Step Synthesis of 2-Arylidenehydrazinyl-4-arylthiazole

An efficient, simple one pot, two step procedure has been developed for the synthesis of 2-arylidenehydrazinyl-4-arylthiazole. The reaction of aromatic aldehyde, thiosemicarbazide and phenacyl bromide gave the desired products in good yield. The first reaction product thiosemicarbazone was obtained on reaction with aromatic aldehyde and thiosemicarbazide; without isolating this directly treated with phenacyl bromide in presence of acidic buffer at room temperature desired product was obtained with simple workup procedure.