2349-58-8

Usage

Uses

Used in Chemical Synthesis Studies:
4,5-Diphenyl-2-imidazolethiol is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure allows it to be a valuable building block in the development of new molecules with specific properties and applications.
Used in Pharmaceutical Industry:
4,5-Diphenyl-2-imidazolethiol is used as a key component in the development of pharmaceuticals, particularly in the synthesis of drugs targeting specific biological pathways. Its chemical properties make it a promising candidate for the creation of novel therapeutic agents.
Used in Material Science:
In the field of material science, 4,5-diphenyl-2-imidazolethiol is used as a component in the development of advanced materials with specific properties, such as improved stability, reactivity, or selectivity. Its unique structure contributes to the overall performance of these materials.
Used in Research and Development:
4,5-Diphenyl-2-imidazolethiol is used as a research tool in various scientific studies, including the investigation of its chemical properties, reactivity, and potential applications in different industries. It serves as a valuable compound for understanding the underlying principles of chemical reactions and interactions.

InChI:InChI=1/C15H12N2S/c18-15-16-13(11-7-3-1-4-8-11)14(17-15)12-9-5-2-6-10-12/h1-10H,(H2,16,17,18)

Upstream product

• 1147550-11-5 ammonium thiocyanate 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 17356-08-0 thiourea 
• 16099-67-5 4,5-diphenylimidazolidine-2-thione 
• 100-52-7 benzaldehyde 

Downstream Products

• 132055-42-6 1-Chloro-3-(4,5-diphenyl-1H-imidazol-2-ylsulfanyl)-propan-2-ol 
• 132055-43-7 1-Oxiranylmethyl-4,5-diphenyl-3-thiiranylmethyl-1,3-dihydro-imidazol-2-one 
• 34035-39-7 6,7-diphenyl-2H,3H,4H-3-hydroxytetrahydroimidazo[2,1-b][1,3]thiazine 
• 951-87-1 meso-1,2-diphenyl-1,2-diaminoethane 
• 668-94-0 4,5-diphenyl-1H-imidazole 
• 50802-87-4 2-p-chlorobenzoylmethylthio-4,5-diphenylimidazole 
• 28440-49-5 2-p-bromobenzoylmethylthio-4,5-diphenylimidazole 
• 28440-48-4 2-benzoylmethylthio-4,5-diphenylimidazole 
• 50802-88-5 2-p-methylbenzoylmethylthio-4,5-diphenylimidazole 
• 28440-50-8 2-p-nitrobenzoylmethylthio-4,5-diphenylimidazole 
• 28440-47-3 2-acetylmethylthio-4,5-diphenylimidazole 
• 39084-24-7 3-(4,5-diphenyl-2-imidazolylthio)-2-butanone 

Relevant academic research and scientific papers

Regio- and stereoselective synthesis of thioglycosides from 4,5-diphenyl- and 3,4,5-triphenylimidazole-2-thione

Six new thioglycosides incorporating the 4,5-diphenyl- and 3,4,5-triphenylimidazole moiety have been successfully synthesized under both conventional and microwave conditions by reaction of the corresponding thiones with aceto-bromosugars in presence of t

Design and synthesis of 4,5-diphenyl-imidazol-1,2,3-triazole hybrids as new anti-diabetic agents: in vitro α-glucosidase inhibition, kinetic and docking studies

Abstract: Fourteen novel 4,5-diphenyl-imidazol-1,2,3-triazole hybrids 8a–n were synthesized with good yields by performing click reaction between the 4,5-diphenyl-2-(prop-2-yn-1-ylthio)-1H-imidazole and various benzyl azides. The synthesized compounds 8a–n were evaluated against yeast α-glucosidase, and all these compounds exhibited excellent inhibitory activity (IC50 values in the range of 85.6 ± 0.4–231.4 ± 1.0?μM), even much more potent than standard drug acarbose (IC50 = 750.0?μM). Among them, 4,5-diphenyl-imidazol-1,2,3-triazoles possessing 2-chloro and 2-bromo-benzyl moieties (compounds 8g and 8i) demonstrated the most potent inhibitory activities toward α-glucosidase. The kinetic study of the compound 8g revealed that this compound inhibited α-glucosidase in a competitive mode. Furthermore, docking calculations of these compounds were performed to predict the interaction mode of the synthesized compounds in the active site of α-glucosidase. Graphic abstract: A novel series of 4,5-diphenyl-imidazol-1,2,3-triazole hybrids 8a–n was synthesized with goodyields by performing click reaction between the 4,5-diphenyl-2-(prop-2-yn-1-ylthio)-1Himidazoleand various benzyl azides. The synthesized compounds 8a–n were evaluated againstyeast α-glucosidase and all these compounds exhibited excellent inhibitory activity (IC50 valuesin the range of 85.6 ± 0.4-231.4 ± 1.0 μM), even much more potent than standard drug acarbose(IC50 = 750.0 μM).[Figure not available: see fulltext.]

Efficient Green Synthesis and Computational Chemical Study of Some Interesting Heterocyclic Derivatives as Insecticidal Agents

A series of 5,5-diarylhydantoin (Dilantin) 3, 4, and 7, imidazole 1, 2, 5, 6, 8, and 9, thiazole 10–12, triazinthione 13, 15, 16, and 17, and thiadiazine 14 derivatives, containing diverse hydrophobic groups, were green synthesized through one-pot stepwise reaction of aromatic aldehydes, vitamin B1, and nitrogen nucleophiles, for example, urea, thiourea, and thiosemicarbazide using grinding technique as well as conventional thermal methods. Such synthesized compounds have potent insecticidal activities; for example, compounds 4, 6, and 17 exhibited the highest insecticidal activity against both Plutella xylostella and Helicoverpa armigera with minimum inhibitory concentration values at 500?μg/mL and LD50 activities at 50?μg/mL. The density functional theory was then applied to explore the structural and electronic characteristics of these compounds. All the synthesized compounds have been characterized based on their elemental analyses and spectral data.

Synthesis and SAR study of 4,5-diaryl-1H-imidazole-2(3H)-thione derivatives, as potent 15-lipoxygenase inhibitors

A series of 4,5-diaryl-1H-imidazole-2(3H)-thione was synthesized and their inhibitory potency against soybean 15-lipoxygenase and free radical scavenging activities were determined. Compound 11 showed the best IC50 for 15-LOX inhibition (IC50 = 4.7 μM) and free radical scavenging activity (IC50 = 14 μM). Methylation of SH at C2 position of imidazole has dramatically decreased the 15-LOX inhibition and radical scavenging activity as it can be observed in the inactive compound 14 (IC50 >250 μM). Structure activity similarity (SAS) showed that the most important chemical modification in this series was methylation of SH group and Docking studies revealed a proper orientation for SH group towards Fe core of the 15-LOX active site. Therefore it was concluded that iron chelating could be a possible mechanism for enzyme inhibition in this series of compounds.

Environmentally benign approach to imidazole 2-thiones

An ecofriendly synthesis of some novel 1,4,5-triarylimidazole-2-thiones/l, 3,4,5-tetraarylimidazole-2-thiones is described. The reaction involves condensation of benzoin with various readily accessible N-substituted thioureas/N,N'-disubstituted thioureas under microwave over recyclable inorganic solid support. This methodology eliminates the usage of solvent and external catalyst in the reaction step and reduces the reaction time from hours to minutes along with remarkable yield enhancement. In addition versatility of various solid supports as catalyst is also studied.

Novel aryloxyalkylthioimidazoles as inhibitors of acyl-CoA: Cholesterol-O-acyltransferase

A series of aryloxyalkcylthioimidazoles have been synthesized and evaluated for their ability to interfere with the enzyme acyl-CoA (cholesterol-O-acyltransferase) (ACAT, EC 2.3.1.26). Most of the molecules possessed a good in vitro ACAT inhibitory activity with IC50 values ranging between 0.1 and 2.0 μM. Some of them, eg, 2-{5-[(4-isobutoxycarbonyl)phenoxy]pentylthio} -4,5-diphenylimidazole 13, 2- {3-[(4-isobutoxycarbonyl)phenoxy]-2-oximopropylthio} -4,5-diphenylimidazole 21, 2-{3-[(4-isobutoxycarbonyl)phenoxy]-2-hydrazonecarboxamidepropylthio}-4,5 -diphenylimidazole 26, 2-[5-(2-pyridoxy)-pentylthio]-4,5-dipilenylimidazole 40 and 2-{5-[(3,5-diterbutyl-4-hydroxy)phenylthiolpentylthio}-4,5-diphenylimidazole 42, were more potent (range of activity 10-90 nM). They were also more potent with respect to the reference CI-976. When administered orally in hyperlipemic rats, at 10 and 50 mg/kg doses, some representative compounds, like 2-{3-[(4-isobutoxycarbonyl)phenoxy]-2-hydroxypropylthio}-4,5 -diphenylimidazole 1, 13 and 26, reduced VLDL/LDL-associated cholesterol levels by 30-50% and increased HDL cholesterol levels by 15-50%. In addition, liver accumulation of esterified cholesterol was counteracted (50-80% reduction) and liver ACAT ex vivo activity was decreased by 70-85%. Finally, the good efficacy displayed in an endogenous model of hypertriglyceridemia strongly supports the hypothesis of a good systemic availability, which constitutes one of the principal properties of a valuable ACAT inhibitor.

Design, Synthesis, and Structure-Activity Relationship Studies for a New Imidazole Series of J774 Macrophage Specific Acyl-CoA:Cholesterol Acyltransferase (ACAT) Inhibitors

Acyl-CoA:cholesterol acyltransferase (ACAT) is the primary enzyme involved in intracellular cholesterol esterification.Arterial wall infiltration by macrophages and subsequent uncontrolled esterification of cholesterol leading to foam cell formation is believed to be an important process which leads to the development of fatty streaks.Inhibitors of the ACAT enzyme may retard this atherogenic process.We have recently discovered a series of imidazoles which are potent in vitro ACAT inhibitors in the J774 macrophage cell culture assay.This paper will describe the design, synthesis, and structure-activity relationship for this very potent series of compounds.

Preparation of omega-substituted alkanamide

A method for the preparation of omega-arylthioalkanamides, especially omega-imidazolylthioalkanamides useful, for example, in the preparation of certain antihypercholesterolemic agents is disclosed. The method involves three steps including an addition reaction between a lactone and an amine to produce an omega-hydroxyalkanamide; a condensation reaction between said omega-hydroxyalkanamide and an alkanesulfonic acid halide or anhydride to produce an alkanesulfonate ester; reaction of said alkanesulfonate ester with a salt of an aromatic mercaptan, especially an imidazole-2-thiol, to produce the omega-imidazolylthioalkanamides.

Acyl-CoA::cholesterol O-Acyl Transferase (ACAT) Inhibitors. 1. 2-(Alkylthio)-4,5-diphenyl-1H-imidazoles as Potent Inhibitors of ACAT

A potent, bioavailable ACAT inhibitor may have beneficial effects in the treatment of atherosclerosis by (i) reducing the absorption of dietary cholesterol, (ii) reducing the secretion of very low density lipoproteins into plasma from the liver, and (iii) preventing the transformation of arterial macrophages into foam cells.We have found that a mevalonate derivative 2, which contains a 4,5-diphenyl-1H-imidazol-2-yl moiety, inhibits rat hepatic microsomal ACAT in vitro and produces a significant hypocholesterolemic effect in the cholesterol-fed rat.Structure-activity relationships for analogues of 2 demonstrate that the 4,5-diphenyl-1H-imidazole moiety is a pharmacophore for inhibition of rat microsomal ACAT.