Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20‐Diisocyanoadociane

Karns, Alexander S.; Ellis, Bryan D.; Roosen, Philipp C.; Chahine, Zeinab; Roch, Karine G. Le; Vanderwal, Christopher D.

doi:10.1002/anie.201906834

Cited by 12 publications

(11 citation statements)

References 29 publications

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“…It maintained activity with a little reduction of potency being 78 nM on Dd2 strain and 51 nM on 3D7 strain with respect of values of 15 and 2 nM for DICA. 247 These result highlights the importance of the isocyanide at the 7 position being equatorial, while the isocyano group at the 20 position is not directly involved in the interaction. Other activity of adociane derivatives as antimalarial compounds are reported in Table 19.…”

Section: Isocyanides In Marine Organisms and Their Biological Activitymentioning

confidence: 92%

“…The epi-isomer at C-20 of DICA was prepared and evaluated for its antimalarial activity. It maintained activity with a little reduction of potency being 78 nM on Dd2 strain and 51 nM on 3D7 strain with respect of values of 15 and 2 nM for DICA . These result highlights the importance of the isocyanide at the 7 position being equatorial, while the isocyano group at the 20 position is not directly involved in the interaction.…”

Section: Isocyano Group In Natural Productsmentioning

confidence: 99%

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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: Isocyanides In Marine Organisms and Their Biological Activitymentioning

confidence: 92%

Section: Isocyano Group In Natural Productsmentioning

confidence: 99%

Medicinal Chemistry of Isocyanides

et al. 2021

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“…[110] Vanderwal ended up finishing this entertaining fight with a knockout blow constituting a 10-step total synthesis (not formal) of 170 starting from dehydrocryptone (178) (Scheme 17). [111] Methodology-Driven Synthesis Many target-orientated syntheses are retrosynthetically designed around a certain type of synthetic methodology. This choice can be inspired by a multitude of reasons, some of which include: (1) testing newly discovered methodology designed inhouse (e.g.…”

Section: Formal Synthesismentioning

confidence: 99%

The Future of Retrosynthesis and Synthetic Planning: Algorithmic, Humanistic or the Interplay?

Williams

Dallaston

2021

Aust. J. Chem.

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The practice of deploying and teaching retrosynthesis is on the cusp of considerable change, which in turn forces practitioners and educators to contemplate whether this impending change will advance or erode the efficiency and elegance of organic synthesis in the future. A short treatise is presented herein that covers the concept of retrosynthesis, along with exemplified methods and theories, and an attempt to comprehend the impact of artificial intelligence in an era when freely and commercially available retrosynthetic and forward synthesis planning programs are increasingly prevalent. Will the computer ever compete with human retrosynthetic design and the art of organic synthesis?

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“…The Sc(OTf) 3 -catalyzed isocyanation has been employed as the key step in the total synthesis of isocyanoterpenoids, which have antiplasmodial and antimalarial activities. Some examples are shown in Figure …”

Section: Catalytic Nucleophilic Isocyanationmentioning

confidence: 99%

Nucleophilic Isocyanation

Yurino

Ohkuma

2020

ACS Omega

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Isonitriles are frequently employed as both substrates for organic transformations and ligands for organometallic chemistry. However, despite the wide application of the isonitriles, their synthesis generally depends on the traditional dehydration of N-formamide. "Nucleophilic isocyanation" using cyanide as an N-nucleophile is another straightforward strategy affording the corresponding isonitriles. This method has been available since the 19th century but is still an immature procedure and is therefore more rarely used. In this review, we summarize the concepts and recent progress in nucleophilic isocyanation, including the relatively rare examples of catalytic isocyanation.

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Concise Synthesis of the Antiplasmodial Isocyanoterpene 7,20‐Diisocyanoadociane

Cited by 12 publications

References 29 publications

Medicinal Chemistry of Isocyanides

Medicinal Chemistry of Isocyanides

The Future of Retrosynthesis and Synthetic Planning: Algorithmic, Humanistic or the Interplay?

Nucleophilic Isocyanation

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