6703-51-1

Basic information

• Product Name: 5,6-Dihydro-imidazo[2,1-b]thiazol-3-one
• Synonyms: 5,6-Dihydro-imidazo(2,1-b)thiazol-3-one; 5,6-Dihydroimidazo[2,1-b][1,3]thiazol-3(2H)-one; Imidazo[2,1-b]thiazol-3(2H)-one, 5,6-dihydro-
• CAS NO: 6703-51-1
• Molecular Formula: C₅H₆N₂OS
• Molecular Weight: 142.18
• Mol File: 6703-51-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 243.5°C at 760 mmHg
• Flash Point: 101.1°C
• Appearance: /
• Density: 1.71g/cm³
• Vapor Pressure: 0.0319mmHg at 25°C
• Refractive Index: 1.82
• CAS DataBase Reference: 5,6-Dihydro-imidazo[2,1-b]thiazol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-Dihydro-imidazo[2,1-b]thiazol-3-one(6703-51-1)
• EPA Substance Registry System: 5,6-Dihydro-imidazo[2,1-b]thiazol-3-one(6703-51-1)

Safety Data

• Hazardous Substances Data: 6703-51-1(Hazardous Substances Data)

Usage

General Description

5,6-Dihydro-imidazo[2,1-b]thiazol-3-one is a chemical compound with a unique molecular structure and diverse potential applications. It is a heterocyclic compound that contains both imidazole and thiazole rings, giving it valuable pharmacological properties. 5,6-Dihydro-imidazo[2,1-b]thiazol-3-one has been investigated for its potential as a drug candidate in the treatment of various diseases, including cancer and neurodegenerative disorders. It has also been studied for its anti-inflammatory and analgesic properties. Furthermore, 5,6-Dihydro-imidazo[2,1-b]thiazol-3-one has shown promise as a building block in organic synthesis and pharmaceutical development due to its versatile reactivity and potential for creating novel chemical structures with valuable biological activities. Overall, 5,6-Dihydro-imidazo[2,1-b]thiazol-3-one is a compound of interest with potential applications in medicinal chemistry and drug discovery.

InChI:InChI=1/C5H6N2OS/c8-4-3-9-5-6-1-2-7(4)5/h1-3H2

Upstream product

• 96-45-7 N,N'-ethylenethiourea 
• 105-39-5 chloroacetic acid ethyl ester 
• 19951-23-6 2-((4,5-dihydro-1H-imidazol-2-yl)thio)acetic acid 
• 91774-37-7 ethyl [(4,5-dihydro-2-imidazolyl)thio]acetate hydrochloride 
• 92114-17-5 (4,5-dihydro-1H-imidazol-2-ylsulfanyl)-thioacetic acid S-(4,5-dihydro-1H-imidazol-2-yl) ester 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 17886-71-4 (Z)-2-benzylidene-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one 
• 17886-71-4 2-benzylidene-5,6-dihydro-imidazo[2,1-b]thiazol-3-one 
• 59816-55-6 3-(4-Chloro-3-dimethylsulfamoylphenyl)-3-hydroxy-2,3,5,6-tetra-hydro-imidazo[2,1-b]thiazol-hydrobromide 
• 1255207-84-1 (2Z)-2-(2-chlorobenzylidene)-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one 
• 1443655-30-8 (2Z)-2-(4-morpholinobenzylidene)-5,6-dihydroimidazo[2,1-b]thiazol-3(2H)-one 

Relevant articles and documents

Identification of (Z)-2-benzylidene-dihydroimidazothiazolone derivatives as tyrosinase inhibitors: Anti-melanogenic effects and in silico studies

As part of our continuous search for novel tyrosinase inhibitors, we designed 5,6-dihydroimindazo[2,1-b]thiazol-3(2H)-one (DHIT) derivatives based on the structure of MHY773; a potent tyrosinase inhibitor with a 2-iminothiazolidin-4-one template. Of the 11 DHIT derivatives synthesized using a Knoevenagel condensation, three DHIT derivatives 1a (IC50 = 36.14 ± 3.90 μM), 1b (IC50 = 0.88 ± 0.91 μM), and 1f (IC50 = 17.10 ± 1.01 μM) inhibited mushroom tyrosinase more than kojic acid (IC50 = 84.41 ± 2.87 μM). Notably, compound 1b inhibited mushroom tyrosinase around 100- and 3.3-fold more potently than kojic acid and MHY773, respectively. Lineweaver-Burk plots demonstrated that compounds 1b and 1f competitively inhibited mushroom tyrosinase, and in silico docking results supported our kinetic results and indicated that these two compounds bind more strongly to the active site of tyrosinase than kojic acid. Docking simulation results using a human tyrosinase homology model confirmed the abilities of 1b and 1f to strongly inhibit human tyrosinase. B16F10 murine melanoma cells were used to investigate whether these two compounds display tyrosinase inhibitory activities and anti-melanogenesis effects in cells. Both compounds were found to significantly and dose-dependently inhibit cellular tyrosinase activity and intracellular and extracellular melanin production more potently than kojic acid. The similarities observed between the cellular tyrosinase and melanogenesis inhibitory effects of 1b and 1f suggest their observed anti-melanogenic effects were due to tyrosinase inhibition. These results indicate that compounds 1b and 1f, which possess the DHIT template, are promising candidates as anti-browning agents and therapeutic agents for hyperpigmentation disorders.

Synthesis and biological evaluation of novel thiazolidinone derivatives as potential anti-inflammatory agents

The modulation of pro-inflammatory cytokines provides a target for controlling inflammatory diseases and attracts much attention in current anti-inflammatory drug development. Here, four series of thiazolidinone derivatives were synthesized and screened for anti-inflammatory activities. A majority of these compounds showed excellent inhibition on the expression of TNF-α and IL-6 in LPS-stimulated macrophages. Discussions are given regarding the structure-activity relationships. Compounds 12d and 12h inhibited LPS-induced TNF-α and IL-6 release in a dose-dependent manner. Furthermore, 12d exhibited a significant protection against LPS-induced septic death in mouse model. Together, these data present a series of new thiazolidinones with potential therapeutic effects in acute inflammatory diseases and they could be important leads in the continuing anti-inflammatory drug research.