Ammonium Salts of 5-(3-Chromenyl)-5H-chromeno[2,3-b]pyridines

Michail N Elinson,Artem N Fakhrutdinov,Yuliya E Ryzhkova

doi:10.3390/m1219

Abstract

The ammonium salts of many drugs have significantly improved the solubility and, accordingly, the bioavailability of medicinal substances in the human body. 5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-5H-chromeno[2,3-b]pyridines are potential NPY1R ligands, which are attractive for antiobesity treatment. Ammonium salts of 5H-chromeno[2,3-b]pyridines were previously unknown. In this communication, it was found that the four-component reaction of salicylaldehyde, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, 4-Hydroxy-2H-chromen-2-one and amines results in the formation of ammonium salts of 5-(3-chromenyl)-5H-chromeno[2,3-b]pyridines. The structure of these previously unknown compounds was confirmed by means of 1H, 13C NMR and IR spectroscopy, mass spectrometry and elemental analysis.

Highlights

Solubility is one of the most important parameters to achieve the desired concentration of a drug in the systemic circulation for coveted pharmacological response [1]
Multicomponent reactions representatool apowerful powerful toolininthe the arsenal of organic synreactions arsenal ofsynorganic syntheMulticomponent reactions represent a represent powerful in the tool arsenal of organic sis; its synergistic utilization with other green chemistry principles would bring organic thesis; its synergistic utilization with other green chemistry principles would bring orthesis; its synergistic utilization with other green chemistry principles would bring orchemists one step to thesynthesis ideal ganic onecloser to the synthesis ideal synthesis ganic chemists onechemists step closer tostep the closer ideal previously out transformation ofof salicylaldehydes, 2We carried previously carried outa amulticomponent multicomponent transformation salicylaldehydes, We previously out carried a multicomponent transformation of salicylaldehydes, aminoprop-1-ene-1,1,3-tricarbonitrile
5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-5H-chromeno[2,3-b]pyridines 8 are known as potential neuropeptide Y1 receptor (NPY1R) ligands, which are attractive for antiobesity treatment [11]

Summary

Introduction

Solubility is one of the most important parameters to achieve the desired concentration of a drug in the systemic circulation for coveted pharmacological response [1]. Solubility plays a significant role in the action of drugs, especially those intended for oral administration. One of the methods for improving solubility is the chemical modification of the drug substance [3] An example of such a modification is the formation of salts. Chromeno[2,3-b]pyridines are one of the significant classes of heterocyclic compounds They have wide pharmacological potential; for example, they exhibit antimicrobial [4], anticancer [5], antirheumatic [6], antimyopic [7] and antiasthmatic [8] activities. In the synthesis of chromeno[2,3-b]pyridines, both multistep classical and multicomponent methods [9] are used These heterocyclic compounds have three conjugated six-membered rings in their structure, which determines their low solubility.

Multicomponent

Four-component

Reaction licylaldehyde

Fragment

General Methods

Conclusions