5344-82-1

Usage

Uses

Used in Agriculture:
1-(2-Chlorophenyl)-2-thiourea is used as an herbicide for controlling the growth of unwanted plants and weeds in various agricultural settings. Its application helps improve crop yield by reducing competition for resources such as nutrients, water, and sunlight.

Reactivity Profile

When heated to decomposition 1-(2-Chlorophenyl)-2-thiourea emits very toxic fumes of chlorides, nitrogen oxides, and sulfur oxides. [EPA, 1998]. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid.

Fire Hazard

When heated to decomposition 1-(2-Chlorophenyl)-2-thiourea emits very toxic fumes of chlorides, nitrogen oxides, and sulfur oxides.

InChI:InChI=1/C7H7ClN2S/c8-5-3-1-2-4-6(5)10-7(9)11/h1-4H,(H3,9,10,11)

Upstream product

• 2740-81-0 2-chlorophenylisothiocyanate 
• 21258-05-9 N-benzoyl-N'-(2-chlorophenyl)thiourea 
• 1147550-11-5 ammonium thiocyanate 
• 95-51-2 o-chloroaniline 
• 137-04-2 2-chloroaniline hydrochloride 
• 53662-47-8 triethylammonium o-chlorophenyl dithiocarbamate salt 
• 45765-25-1 (2-chlorophenyl)cyanamide 
• 333-20-0 potassium thioacyanate 
• 45943-14-4 benzoyl isothiocyanate 

Downstream Products

• 76488-79-4 (2-chloro-phenyl)-(4,5,6,7-tetrahydro-benzothiazol-2-yl)-amine 
• 440107-93-7 2-(2-chloro-anilino)-4-methyl-thiazole-5-carboxylic acid ethyl ester 
• 39130-93-3 2-(2-chloro-anilino)-thiazol-4-one 
• 107773-90-0 5,5-diethyl-1-(2-chloro-phenyl)-2-thio-barbituric acid 
• 51039-90-8 (2-chloro-phenyl)-(4-methyl-thiazol-2-yl)-amine 
• 108237-95-2 2-(2-chloro-anilino)-5-phenyl-thiazol-4-one 
• 136343-79-8 N-(2-chlorophenyl)thiazol-2-amine 
• 19952-47-7 4-chlorobenzo[d]thiazol-2-amine 
• 2740-81-0 2-chlorophenylisothiocyanate 
• 45765-25-1 (2-chlorophenyl)cyanamide 
• 54469-56-6 (4-benzothiazol-2-yl-thiazol-2-yl)-(2-chloro-phenyl)-amine 
• 61108-36-9 (2-chloro-phenyl)-(4'-methyl-2'-phenyl-[4,5']bithiazolyl-2-yl)-amine 
• 61108-50-7 (2-chloro-phenyl)-[2'-(4-chloro-phenyl)-4'-methyl-[4,5']bithiazolyl-2-yl]-amine 
• 103795-43-3 2-(2-chloro-anilino)-5-ethyl-thiazol-4-one 

Relevant academic research and scientific papers

Discovery of aminothiazole derivatives as novel human enterovirus A71 capsid protein inhibitors

Enterovirus A71 (EV-A71), one of the major pathogens that causes hand, foot and mouth disease (HFMD), has seriously threatened the health and safety of young children. In this study, aminothiazole derivatives were synthesized and screened against EV-A71 in Rhabdomyosarcoma (RD) cells. The best compound (12s), with a biphenyl group, showed activity against EV-A71 (EC50: 0.27 μM) but also against a series of different human enteroviruses without significant cytotoxicity (CC50 > 56.2 μM). Mechanistic studies including time-of-drug-addition assays, viral entry assays and microscale thermophoresis (MST) experiments, showed that 12s binds to EV-A71 capsid and blocks the binding between the viral protein VP1 and the relevant human scavenger receptor class B member 2 (hSCARB2).

Self-assembly of a benzothiazolone conjugate into panchromatic fluorescent fibres and their application in cellular imaging

We report the synthesis and characterization of the structures formed by self-assembly of 4-chloro-2(3H)-benzothiazolone (CBT) into panchromatic fibres and their application in cellular imaging. The aggregation properties of the synthesized compound were studied extensively under different solvents and concentrations and their morphologies examined at a supramolecular level by various microscopic techniques such as atomic force microscopy (AFM), fluorescence microscopy, and optical microscopy. Interestingly, the self-assembled structures formed byCBTreveal panchromatic emission properties and show blue, green, and red fluorescence under different excitation wavelengths. The mechanism of structure formation of the self-assemblies was studied through different techniques such as concentration-dependent1H-NMR, ATR-FTIR, UV-visible spectroscopy, and fluorescence spectroscopy. Finally, the utility ofCBTfor cell imaging applications was demonstrated and it can be noted thatCBTwas efficiently taken up by mammalian cells and the cells revealed panchromatic emission in the blue, green, and red channels. The intensities of the fluorescence observed were blue > green > red and the dye interestingly does not exhibit any fluorescence quenching.

Eco-efficient one-pot tandem synthesis of 1-aryl-1H-tetrazol-5-amine by CAN via in situ generated 1-phenylthiourea and heterocumulene

A simple, cost-effective, environmentally benign, and efficient one-pot tandem approach to the synthesis of pharmaceutically important 1-aryl-1H-tetrazole-5-amines 3a-k and 4a-k has been described. The reaction utilized 1-phenyl thiourea, which was generated in situ from aqueous ammonia and isocyanates 1a-k, for the formation of heterocumenes using sodium azide, triethylamine, and ceric ammonium nitrate (CAN) to obtain various aryl-substituted 1H-tetrazole-5-amines (3a-k) in good to excellent yields.

Design, synthesis, and antipoliferative activities of novel substituted imidazole-thione linked benzotriazole derivatives

A new series of benzotriazole moiety bearing substituted imidazol-2-thiones at N1 has been designed, synthesized and evaluated for in vitro anticancer activity against the different cancer cell lines MCF-7(breast cancer), HL-60 (Human promyelocytic leukemia), and HCT-116 (colon cancer). Most of the benzotriazole analogues exhibited promising antiproliferative activity against tested cancer cell lines. Among all the synthesized compounds, BI9 showed potent activity against the cancer cell lines such as MCF-7, HL-60 and HCT-116 with IC50 3.57, 0.40 and 2.63 μM, respectively. Compound BI9 was taken up for elaborate biological studies and the HL-60 cells in the cell cycle were arrested in G2/M phase. Compound BI9 showed remarkable inhibition of tubulin polymerization with the colchicine binding site of tubulin. In addition, compound BI9 promoted apoptosis by regulating the expression of pro-apoptotic protein BAX and anti-apoptotic proteins Bcl-2. These results provide guidance for further rational development of potent tubulin polymerization inhibitors for the treatment of cancer.

Synthesis and biological evaluation of 3-amino-1,2,4-triazole derivatives as potential anticancer compounds

Two series of compounds carrying 3-amino-1,2,4-triazole scaffold were synthesized and evaluated for their anticancer activity against a panel of cancer cell lines using XTT assay. The 1,2,4-triazole synthesis was revisited for the first series of pyridyl derivatives. The biological results revealed the efficiency of the 3-amino-1,2,4-triazole core that could not be replaced and a clear beneficial effect of a 3-bromophenylamino moiety in position 3 of the triazole for both series (compounds 2.6 and 4.6) on several cell lines tested. Moreover, our results point out an antiangiogenic activity of these compounds. Overall, the 5-aryl-3-phenylamino-1,2,4-triazole structure has promising dual anticancer activity.

Novel compound bassed on thiazolidine and use thererof

The present invention relates to a novel compound and uses thereof. More specifically, the present invention provides: a novel compound based on thiazolidine which can effectively inhibit the aggregation of tau, one of the causes of Alzheimerandprime;s disease; and uses thereof. According to the novel compound and uses thereof composed as described above, it is possible to realize an effect of producing a therapeutic agent for Alzheimerandprime;s dementia due to tau aggregation.COPYRIGHT KIPO 2020

CuBr2 mediated synthesis of 2-Aminothiazoles from dithiocarbamic acid salts and ketones

In a one-pot procedure, CuBr2 has been used as a efficient desulfurizing agent in the synthesis of 2-aminothiazoles by the condensation of in situ-generated 1-substituted thioureas from their dithiocarbamic acid salts, with in situ-generated α-bromoketones from ketones. All reactions were carried out under optimized reaction conditions and gave the target products in 61–95% yield.

Convenient one-pot formation of highly functionalized 5-bromo-2-aminothiazoles, potential endocannabinoid hydrolase MAGL inhibitors

Highly functionalized 5-bromo-2-amino-1,3-thiazoles bearing various substituents could be easily prepared by a rapid and efficient one-pot method, using simple starting materials and mild conditions while avoiding the use of metal catalysts or inconvenient reagents such as elemental halogens. These useful products can serve as starting materials for other reactions or as pharmacologically interesting compounds. In our work we have shown that the resulting 5-bromothiazole compounds could lead to monoacylglycerol lipase (MAGL) inhibition in the μM range.

Design, synthesis and molecular docking studies of some thiazole clubbed heterocyclic compounds as possible anti-infective agents

The present work describes synthesis of a series of 5-((1-(4-(4-chlorophenyl)thiazol-2-yl)-3- aryl-1H-pyrazol-4-yl)methylene)-2-(arylimino)thiazolidin-4-one derivatives and their molecular docking and biological evaluation as possible antimalarial, anthelmintic and antimicrobial agents. The synthesis of compounds has been accomplished by adopting suitable synthetic methods. Structures of newly synthesized compounds were characterized and authenticated by spectral methods such as IR, 1H-NMR and mass spectra. Synthesized compounds were screened for their in vitro antimicrobial activity against selected bacterial strains and fungal strains viz. B. subtilis, S. aureus, E. coli, P. fluorescens, C. albicans, C. glabrata and antimalarial studies against P. falciparum. Titled compounds were also tested against Pheretima posthuma (earthworm) for their anthelmintic activity. Molecular docking was done to study the binding modes of the potent compounds against Escherichia coli (PDB ID: 1AB4) and Candida P450DM (PDB ID: 1EA1) enzymes. The results revealed that all the compounds exhibited moderate to significant antimicrobial activities. Antimalarial activity screening revealed that one compound 8i showed significant antimalarial activity with of IC50; 0.59 μg/mL as compared to standard drugs chloroquine (IC50= 0.020 μg/mL) and quinine (IC50; 0.268 μg/mL). The most active compound exhibited the mean paralysis time of 19.2 ± 0.9 min and mean death time of 31.7 ± 2.5 min. It can be concluded that some of the synthesized compounds have remarkable antiinfective, antimalarial and anthelmintic activity and are suitable candidates for further scientific exploration.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).