Applications of MCR-Derived Heterocycles in Drug Discovery

Akritopoulou‐Zanze, Irini; Djurić, Stevan W.

doi:10.1007/7081_2010_46

Cited by 35 publications

(10 citation statements)

References 88 publications

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“…MCR chemistry has been reviewed multiple times in the past in journals and books, however focusing mostly on diverse synthetic and structural aspects. 12,13n,14 The biological activities of MCR derived molecules has been review in the past 12,13j,14t,15 . However there has never been an extensive summary of the biological properties and potential of MCR derived molecules in one review.…”

Section: Introduction: Mcr Space Shape and Diversitymentioning

confidence: 99%

Chemistry and Biology Of Multicomponent Reactions

2012

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Section: Introduction: Mcr Space Shape and Diversitymentioning

confidence: 99%

Chemistry and Biology Of Multicomponent Reactions

2012

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“…The structural diversity in NPs provided novel therapeutic leads in drug discovery endeavours, from medicinal plants, as anticancer and antimicrobial agents, [2] and the diversity can be achieved in an efficient manner by diversity‐oriented synthesis (DOS) [3] . Strategies in DOS for construction of small‐molecule libraries of biological relevance with skeletal and stereochemical diversity comprise build/couple/pair (B/C/P), ring‐distortion, complexity‐generation, cascade and multicomponent reactions [4–11] . DOS can be extended to even NP extracts by direct chemical derivatization to produce diversity‐enhanced extracts [12] …”

Section: Introductionmentioning

confidence: 99%

“…[3] Strategies in DOS for construction of small-molecule libraries of biological relevance with skeletal and stereochemical diversity comprise build/couple/pair (B/C/P), ringdistortion, complexity-generation, cascade and multicomponent reactions. [4][5][6][7][8][9][10][11] DOS can be extended to even NP extracts by direct chemical derivatization to produce diversity-enhanced extracts. [12] Abundant natural products provides an opportunity for derivatization using the versatile transition-metal catalyzed methodologies that enable carbon-carbon bond formations in a combinatorial chemistry approach to afford diverse molecular frameworks.…”

Section: Introductionmentioning

confidence: 99%

Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

Biji

Prabha

Lankalapalli

et al. 2021

The Chemical Record

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Zerumbone is a naturally occurring humulene type sesquiterpene, isolated from the rhizomes of Zingiber zerumbet (L.) Smith with excellent therapeutic potential and is recognized as a valuable synthon for the construction of diverse array of natural product motifs. In this review, we intended to highlight our achievements in utilizing abundant natural product zerumbone and its derivatives for the development of pharmacologically relevant molecular scaffolds. We provided an account of the transition‐metal catalyzed 1,4‐conjugate addition reactions of zerumbone and its derivatives along with palladium‐catalyzed cross‐couplings, transition metal‐based Lewis acid promoted interrupted Nazarov cyclisation reaction with substituted indoles and transannular cyclizations, photo‐induced transformations of zerumbone and its epoxide.

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“…Isocyanides have a rich history in rapidly generating complex molecular targets . Driven by the need for new chemical entities in discovery and pharmaceutical development, isocyanides have emerged as privileged, versatile precursors because they rapidly assemble peptidomimetic pharmacophores and bioactive heterocycles . The diverse isocyanide reactivity is enabled by the carbene-like nature of the terminal carbon that facilitates complex bond constructions: multicomponent reactions, transition metal-catalyzed insertions, and cycloadditions …”

Section: Introductionmentioning

confidence: 99%

Asmic Isocyanide [3 + 2] Cascade to Dihydrooxazoles and Dihydroimidazoles

et al. 2020

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The versatile isocyanide building block Asmic, anisylsulfanylmethylisocyanide, reacts with aldehydes and ketones in a BF 3 •OEt 2 -mediated condensation to afford thioimidoyl-substituted 2,5-dihydrooxazoles. The condensation is distinguished from related base and transition-metal-catalyzed [3 + 2] processes in proceeding via the condensation of aldehydes and ketones with 2 equiv of an isocyanide followed by a molecular rearrangement that installs four new bonds. BF 3 •OEt 2 mediates an analogous condensation of Asmic with imines to generate N-substituted dihydroimidazoles. Mechanistically, BF 3 • OEt 2 activates the isocyanide to facilitate deprotonation evolving to a zwitterion that traps π-electrophiles in a formal [3 + 2] process. A second deprotonation−condensation with Asmic initiates a structural rearrangement involving a sulfanyl elimination− addition transposition sequence. The resulting dihydrooxazoles and dihydroimidazoles contain a thioimidate that serves as a diversification point for further elaboration.

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Applications of MCR-Derived Heterocycles in Drug Discovery

Cited by 35 publications

References 88 publications

Chemistry and Biology Of Multicomponent Reactions

Chemistry and Biology Of Multicomponent Reactions

Transition Metal/Lewis Acid Catalyzed Reactions of Zerumbone for Diverse Molecular Motifs

Asmic Isocyanide [3 + 2] Cascade to Dihydrooxazoles and Dihydroimidazoles

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