Title:4-Aminocoumarin Derivatives as Multifaceted Building Blocks for the Development
of Various Bioactive Fused Coumarin Heterocycles: A Brief Review
Volume: 26
Issue: 17
Author(s): Prasanta Patra*Susanta Patra
Affiliation:
- Department of Chemistry, Jhargram Raj College, Jhargram 721507, India
Keywords:
4-Aminocoumarin, coumarin-fused-heterocycles, condensation-cyclization, C-N coupling, C-C coupling, bioactivity.
Abstract: Aminocoumarins are found to be present in many natural products, pharmaceuticals,
and organic materials. These derivatives demonstrate numerous biological activities including
DNA gyrase, anti-proliferative and anti-breast cancer activities. Among the allaminocoumarin
derivatives, 4-aminocoumarin derivatives have been reported to exhibit anticancer
and anti-fungal properties. 4-Aminocoumarins and their derivatives are important precursors
for the synthesis of coumarin fused N-heterocycles. Due to the presence of an amino
group as well as enamine carbon, it is very reactive towards electrophiles and in most of the
cases, it has a higher tendency to cyclize immediately by the various reaction path ways and
provides the heterocyclic products. Unlike other aromatic amines, it did not give any Schiff
base on reaction with aldehydes or ketones. Lamellarins, ningalin A, ningalin B, schumanniophytin,
santiagonamine, goniothaline, and polyneomarline C are important natural coumarin fused N-heterocycles
and show excellent biological activities, including antitumor, reversal of multidrug resistance, anti-HIV, wound
healing, anti-malarial, anti-hepatitis, and anti-syphilis activities. The synthesized coumarin fused N-heterocycles
have been reported to display Topoisomerases I inhibitory, DYRK1A inhibitory, and anti-cancer activities. Most of
the syntheses of pyrrolo/imidazolo/indolo[3,2-c]coumarin, pyrido/quinolino[3,2-c]coumarins, pyrimidino[
c]coumarin and oxazino[c]coumarin have been synthesized easily from 4-aminocoumarin. This paper reviews
the research data in the literature on the synthesis of bioactive coumarin fused heterocycles using 4-aminocoumarin
derivatives over the period of 2-3 decades. It covers the synthetic applicability of 4-aminocoumarin for the development
of coumarin fused 5-, 6-, and 8-membered ring derivatives via classical reaction protocols, microwavemediated
reactions, organo-catalyzed reactions, transition metal-catalyzed reactions, and green reaction protocols.
