N-substituted Pyrrole-based Scaffolds as Potential Anticancer and Antiviral Lead Structures

Abstract

Undoubtedly, efficient cancer treatment has been a significant challenge for the scientific community over the last decades. Despite tremendous progress made towards this direction, there are still efforts needed to discover new anticancer drugs. In this work, a series of N-substituted pyrrolebased scaffolds have been synthesized and evaluated for antiproliferative activity against a panel of cancer cell lines (L1210, CEM and HeLa). Furthermore, in order to discover new scaffolds as antiviral agents, all the examined compounds were evaluated for activity against different types of DNA and RNA viruses. The key feature of the above structures is the existence of an aromatic ring with at least one hydrogen-bonding donor and acceptor group. Results have shown noteworthy cytostatic activity for three of the synthesized compounds (1, 3 and 9). Especially, compound 1, containing a tropolone ring, proved to be the most promising scaffold (IC50:10-14 µM) for the development of novel potential anticancer agents. In addition, compound 1 has shown modest anti-HSV-1, -HSV2 activity in HEL cell cultures (EC50: 27-40 µM).

Biocatalytic decarboxylative Michael addition for synthesis of 1,4-benzoxazinone derivatives

“…Heterocyclic compounds containing oxygen and nitrogen are of considerable importance due to their occurrence in various natural products and their potential biological activities 1 . 1,4-benzoxazinone derivatives are examples of such heterocycles, exhibiting a wide range of biological activities such as antioxidant 2 , anti‐Alzheimer 3 , antidiabetic 4 , antimalarial 5 , antimicrobial 6 , antibacterial 7 and anticancer 8 .…”

Pyrrole as an Important Scaffold of Anticancer Drugs: Recent Advances

“…Additionally, syntheses of various promising cytotoxic agents containing pyrrole scaffolds have been recently reported (55)(56)(57). The aforementioned data demonstrates the eminent activity of the pyrrole moiety in the search for novel and selective anticancer agents.…”

A Practical Synthesis of Densely Functionalized Pyrroles via a Three-Component Cascade Reaction between Carbohydrates, Oxoacetonitriles, and Ammonium Acetate

“…Pyrroles − are nitrogen heterocyclic compounds embedded in many plant and marine natural products such as chlorophylls, porphyrins, , prodigiosin, and prodoginine . They possess wide bioactivities such as antitumor, − antimycobacterial, − anti-inflammatory, − and antiviral activities. , Several pyrrole-based drugs are commercially available including the blockbuster atorvastatin 1 , sunitinib 2 , and aloracetam 3 (Figure ). Therefore, the development of practical and sustainable methods for the synthesis of densely functionalized pyrroles that are amenable to easy transformations to useful intermediates or final products is of great interest.…”