68301-76-8

Usage

Chemical compound

2-Amino-6-ethyl-3-formylchromone

Derivative of chromone

Naturally occurring compound with diverse biological activities

Pharmacological properties

Anti-inflammatory
Antioxidant
Antitumor agent

Potential applications

Organic synthesis
Fluorescent probe in biological imaging

Upstream product

• 50743-19-6 6-ethyl-4-oxo-4H-1-benzopyran-3-carbonitrile 

Downstream Products

• 53944-31-3 7-ethyl-5H-[1]-benzopyrano [2,3-b] pyridin-5-one 
• 78893-31-9 6-Ethyl-10-oxo-10H-9-oxa-1-aza-anthracene-3-carbaldehyde 
• 68302-09-0 2-amino-7-ethyl-5-oxo-5H-chromeno[2,3-b]pyridine-3-carbonitrile 
• 68302-05-6 7-ethyl-5-oxo-2-phenyl-5H-chromeno[2,3-b]pyridine-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines

5-Oxo-5H-[1]benzopyrano[2,3-b]pyridine-3-carboxylic acids 23 and their tetrazole analogues 24 were synthesized from 4-oxo-4H-1-benzopyran-3-carbonitriles or 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes. When administered intravenously, they exhibited antiallergic activity in a reaginic PCA test in rats. In the carboxylic acid series, the activity was influenced by the substituents at the 2-position and increased substantially in the following order: Me, OMe 2 OH, H NHOMe. On the other hand, in the tetrazole series, 2-unsubsitituted derivatives showed the highest activity. Regardless of the kinds of substituents at positions 2 and 3, compounds bearing an alkyl group, especially an isopropyl group at the 7-position, were superior in activity to the corresponding unsubstituted compounds. Among these alkyl derivatives, 3-carboxylic acid derivatives, i.e., 23c (7-ethyl), 23g (2-amino-7-isopropyl), 23r [2-(methoxyamino)-7-isopropyl], and a 3-tetrazole derivative 24c (7-isopropyl), were 41-184 times as potent as disodium cromoglycate. They also exhibited remarkable activity when administered orally; clinical studies on 23g (AA-673) are in progress.

SYNTHESIS OF 3-SUBSTITUTED-5-OXO-5H-BENZOPYRANOPYRIDINE DERIVATIVES

3-Cyano-. 3-alkoxycarbonyl-, and 3-formyl-5-oxo-5H-benzopyranopyridine dervatives were prepared by reactions of 2-amino-4-oxo-4H-1-benzopyran-3-carboxaldehydes 1 with acetylene derivatives (methods A-C) or with reactive methylene compounds (methods D-E) and also by catalytic hydrogenation of 2-chloro-5-oxo-5H-benzopyranopyridine-3-carbonitriles 12 (method F).