3201-46-5

Basic information

• Product Name: 1,2,4-Oxadiazol-5(4H)-one, 4-methyl-3-phenyl-
• CAS NO: 3201-46-5
• Molecular Formula: C9H8N2O2
• Molecular Weight: 176.175
• Mol File: 3201-46-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,2,4-Oxadiazol-5(4H)-one, 4-methyl-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Oxadiazol-5(4H)-one, 4-methyl-3-phenyl-(3201-46-5)
• EPA Substance Registry System: 1,2,4-Oxadiazol-5(4H)-one, 4-methyl-3-phenyl-(3201-46-5)

Safety Data

• Hazardous Substances Data: 3201-46-5(Hazardous Substances Data)

Usage

Class

Oxadiazoles

Structure

Five-membered heterocyclic ring containing one oxygen and two nitrogen atoms

Substituents

4-methyl and 3-phenyl groups

Applications

Medicinal chemistry and pharmaceuticals

Biological activities

Antioxidant, antimicrobial, and anti-inflammatory effects

Potential uses

Treatment of cancer and other diseases

Synthesis

Building block for novel compounds with therapeutic applications

Upstream product

• 186581-53-3 diazomethane 
• 1456-22-0 3-phenyl-4H-[1,2,4]oxadiazol-5-one 
• 1456-22-0 3-phenyl-1,2,4-oxadiazol-5-one 
• 74-88-4 methyl iodide 
• 20469-54-9 4-methyl-3-phenyl-4H-[1,2,4]oxadiazol-5-ylideneamine 
• 20459-83-0 3-phenyl-4-methyl-1,2,4-oxadiazole-5(4H)-thione 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 100-47-0 benzonitrile 
• 613-92-3 N-hydroxybenzamidine 

Downstream Products

• 10480-53-2 4-benzyl-3-phenyl-1,2,4-oxadiazol-5(4H)-one 

Relevant articles and documents

Development of the 99mTc-Hydroxamamide Complex as a Probe Targeting Carbonic Anhydrase IX

Carbonic anhydrase IX (CA-IX) is regarded as a favorable target for in vivo imaging because of its specific expression in hypoxic regions of tumors. Hypoxia assists tumor propagation and growth and is resistant to chemotherapy and radiotherapy. Here, we designed and synthesized [99mTc]hydroxamamide ([99mTc]Ham) and [99mTc]methyl-substituted-hydroxamamide ([99mTc]MHam) complexes including a bivalent CA-IX ligand, sulfonamide (SA), and ureidosulfonamide (UR). In a cell binding assay, [99mTc]Ham complexes with bivalent SA ([99mTc]SAB2A and [99mTc]SAB2B) and UR ([99mTc]URB2A and [99mTc]URB2B) showed significantly greater uptake into CA-IX high-expressing (HT-29) cells than that into CA-IX low-expressing cells. Since the binding affinity of [99mTc]URB2A and [99mTc]URB2B for CA-IX was significantly higher than that of [99mTc]SAB2A and [99mTc]SAB2B, we additionally synthesized [99mTc]MURB2 (a [99mTc]MHam complex with bivalent UR) and evaluated the CA-IX-specific binding affinity of [99mTc]URB2A, [99mTc]URB2B, and [99mTc]MURB2. Their uptake into HT-29 cells was reduced by the addition of a CA inhibitor, acetazolamide, suggesting their CA-IX-specific binding affinity. A biodistribution study in HT-29 tumor-bearing mice was carried out using [99mTc]URB2A and [99mTc]MURB2 with the highest specificity for HT-29 cells. [99mTc]URB2A showed moderate tumor uptake and reduction by coinjection with acetazolamide; however, the tumor/blood ratio was insufficient for in vivo imaging. These results provided key information for the design of novel Ham-based imaging probes targeting CA-IX.

Tf2NH-catalyzed formal [3 + 2] cycloaddition of oxadiazolones with ynamides: a simple access to aminoimidazoles

Oxadiazolones are first employed as the three-atom coupling partners in the Tf2NH-catalyzed cycloaddition with ynamides. This formal [3 + 2] cycloaddition allows a rapid synthesis of aminoimidazoles with a broad substrate scope. The approach also features a metal-free catalytic cycloaddition process, which may find applications in the synthesis of bioactive molecules. Besides, the resulting N-methyl products can further be readily converted to free N-H aminoimidazoles.