Synthesis of Marine Alkaloids Isonaamine A, Dorimidazole A, and Preclathridine A. Iminophosphorane-Mediated Preparation of 2-Amino-1,4-disubstituted Imidazoles from α-Azido Esters

Molina, Pedro; Fresneda, Pilar M.; Sanz, Miguel Á.

doi:10.1021/jo9819382

Cited by 58 publications

(29 citation statements)

References 36 publications

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“…The chemical profile of Society Islands samples containing a mixture of isonaamine A 1 (Molina et al . ) and isonaamidine A 2 (Nakamura et al . ), also linked to a stronger QS inhibition on our bioassays, were chosen for further investigation (Fig.…”

Section: Resultsmentioning

confidence: 99%

Quorum sensing inhibitors from Leucetta chagosensis Dendy, 1863

Mai

Tintillier

Lucasson

et al. 2015

Letters in Applied Microbiology

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A new type of quorum sensing inhibitors was isolated from the sponge Leucetta chagosensis. One of them inhibits strongly the AI-2 channel of Vibrio harveyi, a marine pathogen of special importance in aquaculture. The activity of five different related compounds, including three new natural products discovered there, was investigated leading to structure-activity relationships which are useful for the design of new quorum sensing inhibitors to control marine infectious pathogens.

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Section: Resultsmentioning

confidence: 99%

Quorum sensing inhibitors from Leucetta chagosensis Dendy, 1863

Mai

Tintillier

Lucasson

et al. 2015

Letters in Applied Microbiology

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“…Since, as described above, the isolation of carbodiimides is not needed when they are prepared through Staudinger reaction, the synthetic pathway depicted in Scheme 12 could be used for the development of a MC sequential process. Indeed, the synthesis of bicyclic guanidines 21 and marine alkaloids 22 has been accomplished by performing such process in a one-pot sequential fashion without isolating the intermediate carbodiimides and using only primary amines as nucleophiles. However, the reactivity of the intermediate carbodiimides has not been studied in details, showing only three examples where the other N-substituent is a neutral aryl moiety such as phenyl, n aphtyl, and tosyl.…”

Section: Reaction With Aminesmentioning

confidence: 99%

Carbodiimides-Mediated Multi Component Synthesis of Biologically Relevant Structures

Bellucci¹,

Volonterio

2012

Organic Chemistry Insights

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Multi-component reactions are very popular because they offer a wealth of products, while requiring only a minimum effort combining many elements of an ideal synthesis, such as operational simplicity, atom economy, bond-forming efficiency, and the access to molecular complexity from simple starting materials. As such, multi-component reactions have become the cornerstones of both combinatorial chemistry and diversity-oriented synthesis and thus playing a central role in the development of modern synthetic methodology for pharmaceutical and drug discovery research. In this Insight we will highlight the development of novel multi-component reactions based on the reactivity of carbodiimides, paying particular attention on their mechanistic features. We will address our attention on the process developed by us and others groups, in these last years, for the synthesis of biologically relevant structures such as, for example, heterocycles and glyco-conjugates.

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“…Protected‐2‐aminoimidazolones 85 were easily converted into protected‐2‐aminoimidazoles 87 by two steps with the treatment with DIBAL‐H and then with methanesulfonyl chloride in 31–67% yield for both steps. In the last step, tosyl‐protected group was cleaved in the presence of samarium diiodide in 90–95% yield (Scheme ) .…”

Section: Synthesis Of the 2‐aminoimidazole Ringmentioning

confidence: 99%

Chemistry of 2‐Aminoimidazoles

Žula

Kikelj

Ilaš

2015

Journal of Heterocyclic Chem

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The 2‐aminoimidazole (2‐AI) ring is used widely as a building block in the design of new biologically active compounds, because of its good physico‐chemical properties and potent activity in various test systems. Many marine alkaloids contain the 2‐AI moiety. As a consequence, many synthetic routes have been developed in the total synthesis of natural compounds. The review covers all synthetic procedures for construction of 2‐AI in particular and its analogs up to December 2014.

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Synthesis of Marine Alkaloids Isonaamine A, Dorimidazole A, and Preclathridine A. Iminophosphorane-Mediated Preparation of 2-Amino-1,4-disubstituted Imidazoles from α-Azido Esters

Cited by 58 publications

References 36 publications

Quorum sensing inhibitors from Leucetta chagosensis Dendy, 1863

Quorum sensing inhibitors from Leucetta chagosensis Dendy, 1863

Carbodiimides-Mediated Multi Component Synthesis of Biologically Relevant Structures

Chemistry of 2‐Aminoimidazoles

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