Across Two Oceans onto the Reef—The Genesis of Marine Natural Products

Scheuer, Paul J.

doi:10.1007/978-1-4899-7565-2_43

Cited by 1 publication

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“…Prof. Scheuer’s interest in chemical marine ecology began when a friend added the nudibranch Phyllidia varicosa to his aquarium. To their surprise, as time went by they witnessed the death of all the fish and shrimp in the aquarium, while the nudibranchs appeared alive and well! Shortly after, 9-isocyanopupukeanane ( 129 ) was isolated from the skin secretion of the nudibranch. This compound is more ichthyotoxic than its epimer with an LD 50 of 1.0 μg/mL versus 2.0 μg/mL .…”

Section: Isocyano Group In Natural Productsmentioning

confidence: 99%

Medicinal Chemistry of Isocyanides

et al. 2021

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In eons of evolution, isocyanides carved out a niche in the ecological systems probably thanks to their metal coordinating properties. In 1859 the first isocyanide was synthesized by humans and in 1950 the first natural isocyanide was discovered. Now, at the beginning of XXI century, hundreds of isocyanides have been isolated both in prokaryotes and eukaryotes and thousands have been synthesized in the laboratory. For some of them their ecological role is known, and their potent biological activity as antibacterial, antifungal, antimalarial, antifouling, and antitumoral compounds has been described. Notwithstanding, the isocyanides have not gained a good reputation among medicinal chemists who have erroneously considered them either too reactive or metabolically unstable, and this has restricted their main use to technical applications as ligands in coordination chemistry. The aim of this review is therefore to show the richness in biological activity of the isocyanidecontaining molecules, to support the idea of using the isocyanide functional group as an unconventional pharmacophore especially useful as a metal coordinating warhead. The unhidden hope is to convince the skeptical medicinal chemists of the isocyanide potential in many areas of drug discovery and considering them in the design of future drugs.

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Section: Isocyano Group In Natural Productsmentioning

confidence: 99%