Mini Review on Pyrido[2,3-c]coumarins Backbone of Santiagonamine Antibiotics

Abstract

Santiagonamine is a natural coumarin fused pyridine, specifically pyrido[2,3-c]coumarin derivative having wound-healing activities and is extracted from stems and branches of the South American shrub Berberis darwinii Hook. It was isolated by Shamma et al. in 1984. Both coumarin and pyridine represent an important class of a multi tasking and multi functional scaffolds in organic synthesis. So, the syntheses of coumarin fused pyridine derivatives have an immense impact in the field of organic and pharmaceutical chemistry due to various biological activities displayed by such classes of compounds as well as for their natural occurrences. The main purpose of this review is to focus on different synthetic methodologies for the synthesis of specifically pyrido[2,3-c]coumarins as it is the backbone of santiagonamine antibiotics. Several methods for the synthesis of pyrido[2,3-c]coumarins have been described in the literature, most of which use 3-aminocoumarin as the starting material. CONTENTS 2-1-5. By Transition Metal-Catalyzed Synthesis 2-2. Synthesis of Pyrido[2,3-c]coumarin from 3-Hydroxycoumarin 2-3. Synthesis of Pyrido[2,3-c]coumarinone 2-4. Total Synthesis of Santiagonamine Natural Product 3. Biological Activity 4. Conclusion

Annulated Heterocyclic[g]Coumarin Composites: Synthetic Approaches and Bioactive Profiling

“…[98] These promising characteristics prompted several medicinal chemists to try fusing this moiety with the coumarin nucleus and explore the pharmacological and biological properties of the resultant AHCCs. [99,100] One example of pyridocoumarin synthesis is an experiment by Majumdar et al. [101] They generated diphenyl substituted pyridocoumarin derivative (152), as shown in Equation 6, by a one-pot reaction between 4-methyl-7-aminocoumarin (149), p-methoxy phenylmethanal (150), and ethynylarene (151).…”

“…The food and drug administration (FDA) has documented the presence of this moiety in the chemical structures of several medications, including omeprazole (1998), abemaciclib (2015), and lorlatinib (2018) [98] . These promising characteristics prompted several medicinal chemists to try fusing this moiety with the coumarin nucleus and explore the pharmacological and biological properties of the resultant AHCCs [99,100] . One example of pyridocoumarin synthesis is an experiment by Majumdar et al.…”

Deaminative ring contraction for the synthesis of polycyclic heteroaromatics: a concise total synthesis of toddaquinoline

“…Polycyclic aromatic natural products exhibit a host of exciting biological properties, 1,2 and their highly varied arene substitution patterns have motivated creative strategies 3 for their assembly. Dehydrojuncusol 1 , 4 litebamine 2 , 5 toddaquinoline 3 , 6 and santiagonamine 4 , 7 serve to emphasize the diverse substitution patterns displayed by biologically active secondary plant metabolites that share the ‘phenanthrene skeleton’ (Fig.…”

Synthesis and Biological Evaluation of Substituted Fused Dipyranoquinolinones

“…Coumarin derivatives are recognized for their biological properties, such as anticancer, anti-inflammatory, antioxidant, antitubercular, anti-Helicobacter pylori, anti-Alzheimer's, antifungal, and anticoagulant [10][11][12][13][14][15][16][17][18][19]. Many fused coumarin derivatives containing pyridine or pyran moieties can also be isolated from natural sources and have shown interesting biological activities; santiagonamine (I) (Figure 1) has been isolated from the extracts of Berberis darwinii Hook presenting wound-healing activity [20,21]; ganocochliarine F (II) can be extracted from Ganoderma cochlear and has been evaluated for renal fibrosis [22]; goniothaline A (III) and goniothaline B (IV) have been isolated from Goniothalamus Australis, an Australian rainforest plant, and evaluated for in vitro antimalarial activity [23,24], and likewise, polynemoraline C (V) has been isolated from the ethanol extracts of the branches and leaves of Polyalthia nemoralis A DC [25], and found to exhibit anticholinergic, anti-inflammatory, antitumor, and antimicrobial activities [26].…”