An Overview of Bioactive 1,3-Oxazole-Containing Alkaloids from Marine Organisms

Abstract

1,3-Oxazole chemicals are a unique class of five-membered monocyclic heteroarenes, containing a nitrogen atom and an oxygen. These alkaloids have attracted extensive attention from medicinal chemists and pharmacologists owing to their diverse arrays of chemical structures and biological activities, and a series of 1,3-oxazole derivatives has been developed into therapeutic agents (e.g., almoxatone, befloxatone, cabotegravir, delpazolid, fenpipalone, haloxazolam, inavolisib). A growing amount of evidence indicates that marine organisms are one of important sources of 1,3-oxazole-containing alkaloids. To improve our knowledge regarding these marine-derived substances, as many as 285 compounds are summarized in this review, which, for the first time, highlights their sources, structural features and biological properties, as well as their biosynthesis and chemical synthesis. Perspective for the future discovery of new 1,3-oxazole compounds from marine organisms is also provided.

Responses of the Macroalga Ulva prolifera Müller to Ocean Acidification Revealed by Complementary NMR- and MS-Based Omics Approaches

“…Two putative macrolide derivatives were up-modulated by the acidification (compounds 9 and 151, respectively, in Figure 7B,E). These compounds' class has been previously identified in algae [109] and is abundant in various marine organisms [110]. Moreover, macrolides have displayed vigorous deterrent activity in laboratory feeding assays against fish [111,112].…”

Access to Mono‐, Di‐ and Tri‐(Het)Arylated Pyrazolo[5,1‐b]oxazoles Using Cyclization, C−H Activation and Suzuki–Miyaura Palladium‐Catalyzed Reactions

“…[1][2][3][4][5][6] Numerous bioactive compounds, including antibiotics, antivirals, and anticancer agents, contain the pyrazole or oxazole pattern as a part of their structure. [7][8][9][10][11][12][13][14] For instance, Mubritinib (tyrosine kinase inhibitor), Aleglitazar (antidiabetic), Ditazole (platelets aggregation inhibitor), and Oxaprozin (COX-2 inhibitor) are known marketed drugs containing an oxazole ring (Figure 1). [15][16][17][18][19][20] Similarly, the pyrazole-containing compound Celecoxib has shown remarkable efficacy as a nonsteroidal antiinflammatory drug (NSAID).…”

“…Pyrazoles and oxazoles have emerged as powerful moieties in natural products and serve as key pharmacophores for drug elaboration [1–6] . Numerous bioactive compounds, including antibiotics, antivirals, and anticancer agents, contain the pyrazole or oxazole pattern as a part of their structure [7–14] . For instance, Mubritinib (tyrosine kinase inhibitor), Aleglitazar (antidiabetic), Ditazole (platelets aggregation inhibitor), and Oxaprozin (COX‐2 inhibitor) are known marketed drugs containing an oxazole ring (Figure 1).…”

Seven New Alkaloids Isolated from Marine Flavobacterium Tenacibaculum discolor sv11

“…Structurally diverse nitrogen-containing heterocycles, such as pyrroles, imidazoles, oxazoles, pyridines, and quinolones, are widely distributed in marine organisms and microorganisms. These naturally occurring secondary metabolites often exhibit significant pharmacological activities, including antibacterial, antifungal, antiparasitic, and anticancer activities [ 1 , 2 , 3 , 4 , 5 , 6 ]. Furthermore, these compounds are often amenable to further structural modifications [ 7 , 8 , 9 , 10 ].…”