17452-09-4

Usage

Uses

Used in Pharmaceutical Industry:
1-PHENYLIMIDAZOLINE-2-THIONE is used as a starting material for the production of pharmaceuticals, given its chemical properties that facilitate the creation of a variety of medicinal compounds. Its ability to inhibit the enzyme thiol protease positions it as a potential candidate for the treatment of certain diseases, thereby contributing to the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, 1-PHENYLIMIDAZOLINE-2-THIONE is utilized as a foundational component in the synthesis of agrochemicals. Its role in this industry is pivotal for the development of products that can enhance crop protection and contribute to agricultural productivity.
Used in Organic Synthesis:
1-PHENYLIMIDAZOLINE-2-THIONE is employed as a research reagent in organic synthesis. Its unique structure and reactivity make it a valuable tool for scientists and researchers working on the synthesis of new organic compounds, thereby expanding the horizons of chemical research and innovation.
Used in Scientific Research:
1-PHENYLIMIDAZOLINE-2-THIONE is also used in the study of its pharmacological properties, providing insights into its potential therapeutic applications. The exploration of its properties can lead to a better understanding of its mechanisms of action, which is essential for the advancement of drug discovery and development.

InChI:InChI=1/C9H8N2S/c12-9-10-6-7-11(9)8-4-2-1-3-5-8/h1-7H,(H,10,12)

Upstream product

• 99361-29-2 3-phenyl-2-thioxo-2,3-dihydro-1H-imidazole-4-carboxylic acid 
• 25373-43-7 N-(2,2-diethoxy-ethyl)-N'-phenyl-thiourea 
• 103-72-0 phenyl isothiocyanate 
• 22483-09-6 2,2-dimethoxyethylamine 
• 2010-15-3 3-phenyl-2-thioxoimidazolidin-4-one 
• 645-36-3 2,2-diethoxy-ethanamine 
• 3129-90-6 isothiocyanic acid 
• 22758-34-5 N-phenyl-2-aminoacetaldehyde diethylacetal 
• 53995-09-8 N'-Phenyl-N-<2,2-dimethoxyaethyl>-thioharnstoff 
• 333-20-0 potassium thioacyanate 
• 62-53-3 aniline 
• 2215-20-5 2-[(phenylcarbamothioyl)amino]acetic acid 

Downstream Products

• 30192-83-7 (1-phenyl-imidazol-2-yl)disulfide 
• 123823-57-4 2-[(2-dimethylamino)benzylthio]-1-phenylimidazole 
• 7164-98-9 1-phenylimidazole 
• 958292-24-5 [(κ2-(phenyl)C3H2N2SSC3H2N2(tert-butyl))CoCl2] 
• 958292-20-1 [(κ2-bis(1-phenyl-imidazol-2-yl)disulfide)CoCl2]*CH2Cl2 
• 40279-09-2 2-methylmercapto-1-phenylimidazole 
• 134478-41-4 1-(1-phenylimidazol-2-ylthio)-4-methylphthalazine 

Relevant academic research and scientific papers

Mass Spectrometry of Substituted 1,3-Dihydro-2H-imidazole-2-thiones

The electron impact mass spectra of the 4-formyl-1,3-dihydro-2H-imidazole-2-thione, its six 1-methyl(n-propyl, n-hexyl)-3-methyl(phenyl)-disubstituted derivatives, and the 1,3-dihydro-1-phenyl-2H-imidazole-2-thione are discussed.The fragmentation pattern is strongly influenced by the alkyl or phenyl N-substituents, as well as by the length of the alkyl chain.The odd-electron ions containing an N-phenyl-substituent, but not a propyl or hexyl group, eject a hydrogen atom from the phenyl ring, while the presence of a long alkyl chain greatly enhances the loss of the sulphyhydryl radical and facilitates the expulsion of several alkenes, and alkyl and alkenyl radicals.

Kinetic and structural investigations of novel inhibitors of human epithelial 15-lipoxygenase-2

Human epithelial 15-lipoxygenase-2 (h15-LOX-2, ALOX15B) is expressed in many tissues and has been implicated in atherosclerosis, cystic fibrosis and ferroptosis. However, there are few reported potent/selective inhibitors that are active ex vivo. In the c

Method for preparing cyclic thiourea compound

The method comprises the following steps: suspending metal hydride in anhydrous THF, dropwise adding ring thiourea in the stirring process, stirring at room temperature after completion of stirring, stirring at room temperature, TLC monitoring reaction co

Facile conversion of amino acids into 1-alkyl imidazole-2-thiones, and their oxidative desulfurization to imidazoles with benzoyl peroxide

Glycine was acylated with isothiocyanates and condensed to 3-alkyl 2-thiohydantoins, which were reduced with a mixture of sodium borohydride and lithium chloride and dehydrated to 1-alkyl imidazole-2-thiones. These were oxidatively desulfurized to imidazoles with benzoyl peroxide. No chromatography was required for model compounds. The methods developed were used to elaborate tyrosine to 1,4-di(p-methoxybenzyl)imidazole, a common intermediate in the syntheses of three imidazoles from the sponge Leucetta. Georg Thieme Verlag Stuttgart.

New bis(mercaptoimidazolyl)(pyrazolyl)borate ligands and their zinc complex chemistry

Nine new tripodal NS2 ligands of the bis(mercaptoimidazolyl)(pyrazolyl)borate type with varying 3-R-mercaptoimidazolyl moieties were prepared as their potassium salts. Treatment with zinc salts yielded the complex types L·Zn-Cl, L·Zn-I, L·Zn-ONO2, L·Zn-OClO3 and [L·Zn(imidazole)]ClO4. Attempts at the formation of L·Zn-OH or cationic L·Zn complexes resulted in dismutation and formation of ZnL2 complexes. Hydrolytic destruction yielded one [OZn4(thiooimidazolate)6] complex. The ZnS2NO coordination which is present in the enzyme-substrate complex of alcohol dehydrogenase could be successfully modelled by an [L·Zn(C2H5OH)]+ complex. The L·Zn-X complexes showed very low catalytic activity in the dehydrogenation of 2-propanol or the hydrogenation of p-nitrobenzaldehyde. The new compounds were identified by a total of 12 structure determinations. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

One-pot preparation of 1-substituted imidazole-2-thione from isothiocyanate and amino acetal

Isothiocyanates were treated with amino acetal and cone. HCl (0.5 eq.) successively in one-pot to afford 1-substituted imidazole-2-thiones in good yields.

2-[(2-Aminobenzyl)sulfinyl]-1-(2-pyridyl)-1,4,5,6- tetrahydrocyclopent[d]imidazoles as a novel class of gastric H+/K+-ATPase inhibitors

Substituted 2-sulfinylimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase. The 4,5-unsubstituted imidazole series 6-11 and the 1,4,5,6-tetrahydrocyclopent[d]imidazole series 12 were found to be potent inhibitors of the acid secretory enzyme H+/K+- ATPase. Structure-activity relationships indicate that the substitution of 2- pyridyl groups at the 1-position of the imidazole moiety combined with (2- aminobenzyl)sulfinyl groups at the 2-position leads to highly active compounds with a favorable chemical stability. Other substitution patterns in the imidazole moiety result in reducing biological activities. 2-[(2- Aminobenzyl)sulfinyl]-1-[2-(3-methylpyridyl)]-1,4,5,6- tetrahydrocyclopent[d]imidazole (12h, T-776) was selected for further development as a potential clinical candidate. Extensive study on the acid degradation of 12h indicates a mechanism of action different from that of omeprazole, the first H+/K+-ATPase inhibitor introduced to the market.

Nitroimidazoles: Part IV - 1-Sulphonyl(carbamoyl/thiocarbamoyl)-3-(1-methyl-5-nitroimidazol-2-yl)-2-imidazolidinones

Sulphone (5) is condensed with sodium salts of a variety of 1-suplphonyl (7), 1-thiocarbamoyl (9) and 1-carbonyl (10)-2-imidazolidinones to give 3-(2-imidazolyl)imidazolidinones (12), (13) and (14) respectively, out of which 1-methylsulphonyl-3-(1-methyl-5-nitro-imidazol-2-yl)-2-imidazolidinone (12a) is undergoing clinical trials as an antiamoebic-antitrichomonal agent. 15 and 16 are analougous imidazolidinones, while 17 and 18 are benzimidazolone derivatives.The reaction of 5 with the sodium salt of 2-imidazolidinone gives rise to the mono and bis-condensation products 21 and 22 respectively.Several other minor byproducts, 23-27 have been identified. 23, 26 and 27 arise from 21. 24, a transformation product of 5 leads to the ether 25 by a displacement reaction.A second synthesis of 12a involves the nitration of imidazolylimidazolidinone (30) in the terminal step, with 30 becoming available from 1-methyl-2-aminoimidazole (28) and chloroethyl isocyanate, and subsequent reaction of resultant 29 with methanesulphonyl chloride.The higher ring homologue, 33 of 12a is synthesised in poor yield from 5 and 1-methylsulphonylhexahydropyrimidinone.Treatment of 12a and 13a with KI in DMF leads to the isomeric 4-nitro derivatives 38a, b and desmethyl derivates 37a, b.Treatment of 12a with triethyloxonium fluoroborate affords the quaternary isothiourea (35) which is hydrolysed to 36.Treatment of 12a and 13a with aqeous alkali leads to cleavage of imidazolidinone ring to form the ethylenediamines 31a and b.Position isomers 41 and 43 of 12a are respetcively obtained by the reaction of 1-methyl-4-nitro-5-chloro-(40)-, and 1-methyl-5-nitro-4-chloro-(42)-imidazoles with 1-methylsulphonyl-ethylene urea.Treatment of the last compound with various reactive halides, e.g. 2-chlorobenzothiazole, yields several analogues 44a-i of 12a while niridazole (45) and methylsulphonyl chloride affords nitrothiazole analogue 46.