175603-75-5

Basic information

• Product Name: 2-amino-4-methyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• Synonyms: 2-amino-4-methyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• CAS NO: 175603-75-5
• Molecular Formula: C11H12N2O2
• Molecular Weight: 204.22518
• Mol File: 175603-75-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 201-202 °C(Solv: ethanol (64-17-5))
• Boiling Point: 463.8±45.0 °C(Predicted)
• Appearance: /
• Density: 1.27±0.1 g/cm3(Predicted)
• PKA: 3.45±0.40(Predicted)
• CAS DataBase Reference: 2-amino-4-methyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-methyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(175603-75-5)
• EPA Substance Registry System: 2-amino-4-methyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile(175603-75-5)

Safety Data

• Hazardous Substances Data: 175603-75-5(Hazardous Substances Data)

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 75-07-0 acetaldehyde 
• 109-77-3 malononitrile 
• 1508-07-2 1,1-dicyanopropene 

Relevant articles and documents

Biocatalytic tandem multicomponent reactions for one-pot synthesis of 2-Amino-4H-Pyran library and in vitro biological evaluation

A simple, effective and ecofriendly biocatalytic method has been developed to construct 2-amino-4H-pyrans via tandem multi-component reaction (MCR) of aldehyde, malononitrile and ethyl acetoacetate in one pot. The catalytic activity of lipases in differen

New Insight into the Structure-Activity Relationships of the Selective Excitatory Amino Acid Transporter Subtype 1 (EAAT1) Inhibitors UCPH-101 and UCPH-102

In the present study, we made further investigations on the structure-activity requirements of the selective excitatory amino acid transporter 1 (EAAT1) inhibitor, 2-amino-4-(4-methoxyphenyl)-7-(naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101), by exploring 15 different substituents (R1) at the 7-position in combination with eight different substituents (R2) at the 4-position. Among the 63 new analogues synthesized, we identified a number of compounds that unexpectedly displayed inhibitory activities at EAAT1 in light of understanding the structure-activity relationship (SAR) of this inhibitor class extracted from previous studies. Moreover, the nature of the R1 and R2 substituents were observed to contribute to the functional properties of the various analogues in additive and non-additive ways. Finally, separation of the four stereoisomers of analogue 14 g (2-amino-4-([1,1′-biphenyl]-4-yl)-3-cyano-7-isopropyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene) was carried out, and in agreement with a study of a related scaffold, the R configuration at C4 was found to be mandatory for inhibitory activity, while both the C7 diastereomers were found to be active as EAAT1 inhibitors. A study of the stereochemical stability of the four pure stereoisomers 14 g-A-D showed that epimerization takes places at C7 via a ring-opening, C-C bond rotation, ring-closing mechanism. Inhibition of glutamate uptake: 63 new analogues of the selective EAAT1 inhibitor UCPH-101 were synthesized and characterized pharmacologically. Analogues that unexpectedly displayed inhibitory activities at EAAT1 were identified. Furthermore, separation of the four stereoisomers of analogue 14 g revealed that, in agreement with a study of a related scaffold, the R configuration at C4 is mandatory for inhibitory activity, whereas both C7 diastereomers are active as EAAT1 inhibitors.