67618-23-9

Basic information

• Product Name: N-(1,3-BENZODIOXOL-5-YL)-N'-BENZOYLTHIOUREA
• Synonyms: N-(1,3-BENZODIOXOL-5-YL)-N'-BENZOYLTHIOUREA;1-benzoyl-3-(2H-1,3-benzodioxol-5-yl)thiourea
• CAS NO: 67618-23-9
• Molecular Formula: C₁₅H₁₂N₂O₃S
• Molecular Weight: 300.33
• Mol File: 67618-23-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(1,3-BENZODIOXOL-5-YL)-N'-BENZOYLTHIOUREA(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1,3-BENZODIOXOL-5-YL)-N'-BENZOYLTHIOUREA(67618-23-9)
• EPA Substance Registry System: N-(1,3-BENZODIOXOL-5-YL)-N'-BENZOYLTHIOUREA(67618-23-9)

Safety Data

• Hazardous Substances Data: 67618-23-9(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 14268-66-7 benzo[1,3]dioxolo-5-ylamine 
• 532-55-8 Benzoyl isothiocyanate 

Downstream Products

• 469891-25-6 N-(benzo[d][1,3]dioxol-5-yl)-4-(4-chlorophenyl)thiazol-2-amine hydrobromide 
• 65069-55-8 1-(benzo[d][1,3]dioxol-5-yl)thiourea 

Relevant articles and documents

Multi-dimensional target profiling of N,4-diaryl-1,3-thiazole-2-amines as potent inhibitors of eicosanoid metabolism

Eicosanoids like leukotrienes and prostaglandins play a considerable role in inflammation. Produced within the arachidonic acid (AA) cascade, these lipid mediators are involved in the pathogenesis of pain as well as acute and chronic inflammatory diseases like rheumatoid arthritis and asthma. With regard to the lipid cross-talk within the AA pathway, a promising approach for an effective anti-inflammatory therapy is the development of inhibitors targeting more than one enzyme of this cascade. Within this study, thirty N-4-diaryl-1,3-thiazole-2- amine based compounds with different substitution patterns were synthesized and tested in various cell-based assays to investigate their activity and selectivity profile concerning five key enzymes involved in eicosanoid metabolism (5-, 12-, 15-lipoxygenase (LO), cyclooxygenase-1 and -2 (COX-1/-2)). With compound 7, 2-(4-phenyl)thiazol-2-ylamino)phenol (ST-1355), a multi-target ligand targeting all tested enzymes is presented, whereas compound 9, 2-(4-(4-chlorophenyl)thiazol-2-ylamino)phenol (ST-1705), represents a potent and selective 5-LO and COX-2 inhibitor with an IC50 value of 0.9 ± 0.2 μM (5-LO) and a residual activity of 9.1 ± 1.1% at 10 μM (COX-2 product formation). The promising characteristics and the additional non-cytotoxic profile of both compounds reveal new lead structures for the treatment of eicosanoid-mediated diseases.

Improved Procedures for the Preparation of Cycloalkyl-, Arylalkyl-, and Arylthioureas

An improved procedure for the preparation of arylthioureas consists of the reaction of benzoyl isothiocyanate with anilines in acetone and debenzoylation of the resultant N-aryl-N'-benzoylthioureas with 5percent aqueous sodium hydroxide.Bicycloalkylthioureas and N-(arylalkyl)thioureas (e.g. 9H-9-fluorenylthiourea) are directly prepared from the corresponding isothiocyanates and ammonia.