185613-91-6

Basic information

• Product Name: 4-BENZO[1,3]DIOXOL-5-YL-THIAZOL-2-YLAMINE
• Synonyms: 4-BENZO[1,3]DIOXOL-5-YL-THIAZOL-2-YLAMINE;5-(2-AMINO-4-THIAZOLYL)-1,3-BENZODIOXOLE;4-(1,3-BENZODIOXOL-5-YL)-1,3-THIAZOL-2-AMINE;4-(1,3-BENZODIOXOL-5-YL)-1,3-THIAZOL-2-YLAMINE;4-(2H-1,3-Benzodioxol-5-yl)-1,3-thiazol-2-amine;4-(benzo[d][1,3]dioxol-5-yl)thiazol-2-amine
• CAS NO: 185613-91-6
• Molecular Formula: C₁₀H₈N₂O₂S
• Molecular Weight: 220.25
• Mol File: 185613-91-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 4-BENZO[1,3]DIOXOL-5-YL-THIAZOL-2-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BENZO[1,3]DIOXOL-5-YL-THIAZOL-2-YLAMINE(185613-91-6)
• EPA Substance Registry System: 4-BENZO[1,3]DIOXOL-5-YL-THIAZOL-2-YLAMINE(185613-91-6)

Safety Data

• Hazardous Substances Data: 185613-91-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Benzo[1,3]dioxol-5-yl-thiazol-2-ylamine is used as a potential active pharmaceutical ingredient for the development of new drugs due to its potential antimicrobial, antifungal, and antitumor properties. Its unique structure may offer novel mechanisms of action against various diseases and conditions.
Used in Antimicrobial Applications:
In the field of antimicrobial research, 4-Benzo[1,3]dioxol-5-yl-thiazol-2-ylamine is being explored as a potential antimicrobial agent. It may be effective against a range of bacteria and could contribute to the development of new antibiotics to combat drug-resistant infections.
Used in Antifungal Applications:
4-Benzo[1,3]dioxol-5-yl-thiazol-2-ylamine is also being investigated for its potential as an antifungal agent. Its heterocyclic structure may provide a new approach to treating fungal infections, which are becoming increasingly resistant to existing antifungal drugs.
Used in Antitumor Applications:
4-BENZO[1,3]DIOXOL-5-YL-THIAZOL-2-YLAMINE is being studied for its potential antitumor properties, which could make it a candidate for cancer therapy. Its heterocyclic nature may allow it to interact with cellular targets in ways that inhibit tumor growth or induce cell death in cancerous cells.
Used in Medicinal Chemistry Research:
4-Benzo[1,3]dioxol-5-yl-thiazol-2-ylamine serves as a valuable compound in medicinal chemistry research, where it is being investigated for its potential to interact with biological targets and modulate biological pathways. This research could lead to a better understanding of its mechanisms of action and the development of new therapeutic agents.

Upstream product

• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 17356-08-0 thiourea 
• 40288-65-1 1-(benzo[1,3]dioxol-5-yl)-2-bromoethanone 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 

Downstream Products

• 488815-95-8 2-[4-(benzo[1,3]dioxol-5-yl)-thiazol-2-ylaminocarbonyl]-benzoic acid 

Relevant articles and documents

Synthesis of 2-aminothiazoles via rhodium-catalyzed carbenoid insertion/annulation of sulfoxonium ylides with thioureas

Sulfoxonium ylides as carbene precursors couple smoothly with thioureas in the presence of 5 mol% of rhodium(II) acetate dimmer via carbenoid insertion to afford the corresponding 2-aminothiazoles with high chemoselectivity, providing a facile and efficient approach to access a variety of 2-aminothiazole derivatives with good functional groups tolerance.

Structure-Based Design of N-(5-Phenylthiazol-2-yl)acrylamides as Novel and Potent Glutathione S-Transferase Omega 1 Inhibitors

Using reported glutathione S-transferase omega 1 (GSTO1-1) cocrystal structures, we designed and synthesized acrylamide-containing compounds that covalently bind to Cys32 on the catalytic site. Starting from a thiazole derivative 10 (GSTO1-1 IC50 = 0.6 μM), compound 18 was synthesized and cocrystallized with GSTO1. Modification on the amide moiety of hit compound 10 significantly increased the GSTO1-1 inhibitory potency. We solved the cocrystal structures of new derivatives, 37 and 44, bearing an amide side chain bound to GSTO1. These new structures showed a reorientation of the phenyl thiazole core of inhibitors, 37 and 44, when compared to 18. Guided by the cocrystal structure of GSTO1:44, analogue 49 was designed, resulting in the most potent GSTO1-1 inhibitor (IC50 = 0.22 ± 0.02 nM) known to date. We believe that our data will form the basis for future studies of developing GSTO1-1 as a new drug target for cancer therapy.

Synthesis, biological evaluation, and metabolic stability of chlorogenic acid derivatives possessing thiazole as potent inhibitors of α-MSH-stimulated melanogenesis

A series of catechol and dioxolane analogs containing thiazole CGA derivatives have been synthesized and evaluated for their inhibitory activity against α-MSH. The inhibitory activity was improved by replacing an α,β-unsaturated carbonyl of previously reported caffeamides with thiazole motif. Surprisingly, compound 7d, one of the derivatives of dioxolane analogs, displayed the most potent inhibitory activity with an IC50 of 0.90 μM. Further studies on metabolic stability and bioactivation potential were also accomplished.

Novel Chlorogenic Acid Derivatives and Anti-Inflammatory and Skin Whitening Composition Comprising the Same

The present invention relates to a novel chlorogenic acid derivative compound having an anti-inflammatory activity and a skin whitening activity, a use of the compound, and a manufacturing method of the compound. The compound of the present invention inhibits an NF- κB activation path, and inhibits an activity of α-melanocyte-stimulating hormone (α-MSH), thereby having the anti-inflammatory activity and the skin whitening activity. The compound of the present invention can be developed as a treating agent of inflammatory diseases and a skin whitening agent.

I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea

A concise and efficient one-pot process from easily available methyl ketones/unsaturated methyl ketones and thiourea was developed for the synthesis of 2-aminothiazoles under the media of I2/CuO. The method can highly stereoselectivity obtain the E-isomers of 4-ethenyl-2-aminothiazoles (5a-f). All these target molecules were characterized by NMR, HRMS and IR spectra. Furthermore, the target compounds 3c and 5b were further determined by X-ray crystallographic analysis.