An Overview on the Synthesis of Lamellarins and Related Compounds with Biological Interest

• Published in: Molecules (Basel, Switzerland) Switzerland), 2024-08, Vol.29 (17), p.4032
• Main Authors: Mitsiou, Vasiliki-Panagiota M, Antonaki, Anastasia-Maria N, Douka, Matina D, Litinas, Konstantinos E
• Format: Article
• Language: English
• Subjects: Acids; Analytical chemistry; Animals; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; azacoumestans; Biological Products - chemical synthesis; Biological Products - chemistry; Biological Products - pharmacology; coumarins; Coumarins - chemical synthesis; Coumarins - chemistry; Coumarins - pharmacology; Cytotoxicity; Heterocyclic Compounds, 4 or More Rings; Humans; isoazacoumestans; isolamellarins; isoquinoline; Isoquinolines - chemical synthesis; Isoquinolines - chemistry; Isoquinolines - pharmacology; lamellarins; Molecular Structure; Oxidation; Pyrroles - chemical synthesis; Pyrroles - chemistry; Pyrroles - pharmacology
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules29174032

Lamellarins are natural products with a [3,4]-fused pyrrolocoumarin skeleton possessing interesting biological properties. More than 70 members have been isolated from diverse marine organisms, such as sponges, ascidians, mollusks, and tunicates. There is a continuous interest in the synthesis of these compounds. In this review, the synthetic strategies for the synthesis of the title compounds are presented along with their biological properties. Three routes are followed for the synthesis of lamellarins. Initially, pyrrole derivatives are the starting or intermediate compounds, and then they are fused to isoquinoline or a coumarin moiety. Second, isoquinoline is the starting compound fused to an indole moiety. In the last route, coumarins are the starting compounds, which are fused to a pyrrole moiety and an isoquinoline scaffold. The synthesis of isolamellarins, azacoumestans, isoazacoumestans, and analogues is also described. The above synthesis is achieved via metal-catalyzed cross-coupling, [3 + 2] cycloaddition, substitution, and lactonization reactions. The title compounds exhibit cytotoxic, multidrug resistance (MDR), topoisomerase I-targeted antitumor, anti-HIV, antiproliferative, anti-neurodegenerative disease, and anti-inflammatory activities.