111861-30-4

Basic information

• Product Name: ethyl 2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate
• Synonyms: ethyl 2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate
• CAS NO: 111861-30-4
• Molecular Formula: C₁₈H₁₇NO₄
• Molecular Weight: 311.33188
• Mol File: 111861-30-4.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate(111861-30-4)
• EPA Substance Registry System: ethyl 2-amino-7-hydroxy-4-phenyl-4H-chromene-3-carboxylate(111861-30-4)

Safety Data

• Hazardous Substances Data: 111861-30-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 108-46-3 recorcinol 
• 2169-69-9 ethyl (E)-2-cyano-3-phenyl-2-propenoate 
• 14533-87-0 (Z)-ethyl 2-cyano-3-phenylacrylate 
• 2025-40-3 ethyl benzylidenecyanoacetate 

Relevant articles and documents

Optimisation of estrogen receptor subtype-selectivity of a 4-Aryl-4H-chromene scaffold previously identified by virtual screening

4-Aryl-4H-Chromene derivatives have been previously shown to exhibit anti-proliferative, apoptotic and anti-angiogenic activity in a variety of tumor models in vitro and in vivo generally via activation of caspases through inhibition of tubulin polymerisation. We have previously identified by Virtual Screening (VS) a 4-aryl-4H-chromene scaffold, of which two examples were shown to bind Estrogen Receptor α and β with low nanomolar affinity and 20-fold selectivity for α over β and low micromolar anti-proliferative activity in the MCF-7 cell line. Thus, using the 4-aryl-4H-chromene scaffold as a starting point, a series of compounds with a range of basic arylethers at C-4 and modifications at the C3-ester substituent of the benzopyran ring were synthesised, producing some potent ER antagonists in the MCF-7 cell line which were highly selective for ERα (compound 35; 350-fold selectivity) or ERβ (compound 42; 170-fold selectivity).

Synthesis of new condensed 2-amino-4H-pyran-3-carbonitriles and of 2-aminoquinoline-3-carbonitriles

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NITRILES IN HETEROCYCLIC SYNTHESIS: NOVEL SYNTHESES OF BENZOPYRANS, NAPHTHOPYRANS, NAPHTHOPYRANS, PYRANOQUINOLINES AND PYRANOQUINOLINES

Benzopyrans, naphthopyrans, naphthopyrans, pyranoquinolines, and pyranoquinolines were synthesized by the reaction of cinnamonitriles with phenols, naphthols, 8-hydroxyquinoline, and 1-methyl-4-hydroxy-2-quinolone.