3-(4-AMINO-PHENYL)-CHROMEN-2-ONE

• CAT Number: M128355
• CAS Number: 1218-54-8
• Molecular Formula: C15H11NO2
• Molecular Weight: 237.25
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 3-(4-aminophenyl)chromen-2-one
• InChI: InChI=1S/C15H11NO2/c16-12-7-5-10(6-8-12)13-9-11-3-1-2-4-14(11)18-15(13)17/h1-9H,16H2
• InChIKey: LYIBWAQRUZXFGC-UHFFFAOYSA-N
• SMILES: C1=CC=C2C(=C1)C=C(C(=O)O2)C3=CC=C(C=C3)N

3-(4-amino-phenyl)-chromen-2-one（Cat No.:M128355） is a chemical compound with a chromenone backbone substituted at the 3-position with a phenyl ring bearing an amino group at the para position. This compound is of interest in medicinal chemistry due to its potential pharmacological properties. Chromenone derivatives have been studied for their diverse biological activities, including antioxidant, anti-inflammatory, and anticancer effects. The specific substitution pattern in 3-(4-amino-phenyl)-chrome-2-one may confer unique properties that could be explored for therapeutic applications.

Reference

[1]. J Med Chem. 2011 Apr 14;54(7):2331-40. doi: 10.1021/jm101489w. Epub 2011 Mar 10.
Design, synthesis, and evaluation of coumarin-based molecular probes for imaging of myelination.
Wang C(1), Wu C, Zhu J, Miller RH, Wang Y.
Author information: (1)Division of Radiopharmaceutical Science, Case Center for Imaging Research, Department of Radiology, Case Western Reserve University, Cleveland, Ohio 44106, United States.
Myelination represents one of the most fundamental biological processes in the vertebrate nervous system. Abnormalities and changes in myelination in the central nervous system (CNS) are seen in many neurodegenerative disorders, such as multiple sclerosis (MS). A long-standing goal has been to directly detect and quantify myelin content in order to facilitate diagnosis and therapeutic treatments of myelin-related diseases. In the course of our studies, we have developed a series of small-molecule probes (SMP) as myelin-imaging agents. Among them are coumarin derivatives, which exhibit promising brain permeability and myelin-binding properties. Herein we report a full account of the design and synthesis of coumarin-based SMPs as myelin-imaging agents. Systematic evaluation of these SMPs in both the CNS and peripheral nervous system (PNS) allowed us to identify some lead agents for potential use as fluorescent dyes for intraoperative nerve mapping in surgical operations or as radiotracers for positron emission tomography (PET) imaging of myelination.
DOI: 10.1021/jm101489w PMCID: PMC3099240 PMID: 21391687

[2]. J Histochem Cytochem. 2010 Jul;58(7):611-21. doi: 10.1369/jhc.2010.954842. Epub 2010 Mar 30.
In situ fluorescence imaging of myelination.
Wang C(1), Popescu DC, Wu C, Zhu J, Macklin W, Wang Y.
Author information: (1)Case Center for Imaging Research, Department of Radiology, Case Western Reserve University, Cleveland, OH 44106, USA.
We describe a novel fluorescent dye, 3-(4-aminophenyl)-2H-chromen-2-one (termed case myelin compound or CMC), that can be used for in situ fluorescent imaging of myelin in the vertebrate nervous system. When administered via intravenous injection into the tail vein, CMC selectively stained large bundles of myelinated fibers in both the central nervous system (CNS) and the peripheral nervous system (PNS). In the CNS, CMC readily entered the brain and selectively localized in myelinated regions such as the corpus callosum and cerebellum. CMC also selectively stained myelinated nerves in the PNS. The staining patterns of CMC in a hypermyelinated mouse model were consistent with immunohistochemical staining. Similar to immunohistochemical staining, CMC selectively bound to myelin sheaths present in the white matter tracts. Unlike CMC, conventional antibody staining for myelin basic protein also stained oligodendrocyte cytoplasm in the striatum as well as granule layers in the cerebellum. In vivo application of CMC was also demonstrated by fluorescence imaging of myelinated nerves in the PNS.
DOI: 10.1369/jhc.2010.954842 PMCID: PMC2889403 PMID: 20354147