A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose

Ludek, Olaf R.; Márquez, Víctor E.

doi:10.1016/j.tet.2009.08.035

Cited by 20 publications

(13 citation statements)

References 39 publications

(44 reference statements)

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“…6,8‐Dioxabicyclo[3.2.1]octane is a major structural unit of insect pheromones (frontalin and brevicomin), synthetic analogs of which are widely used as signal compounds for pest control . The cyclopentenol core is a structural fragment of nucleoside antibiotics showing antiviral and antimicrobial activity …”

Section: Introductionmentioning

confidence: 99%

Two classes of heterocycles—6,8‐dioxabicyclo[3.2.1]octanes and cyclopentenols from the same reagents: A quantum‐chemical comparison of mechanism

Vitkovskaya

Orel

Кобычев

et al. 2018

Int J of Quantum Chemistry

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Most of the strategies for the synthesis of 6,8‐dioxabicyclo[3.2.1]octanes (BCO) and cyclopentenols (CP), which show high biological and pharmaceutical activity, are multistage and/or require hardly accessible starting materials and catalysts. The general method for BCO and CP preparation in a single preparative stage from two simple reagents, ketones and acetylene, under the action of an available super‐basic catalytic system KOH/DMSO becomes promising for the development of general approaches to the design of these classes of biologically active compounds. The mechanism of competing reactions yielding both 7‐methylene‐6.8‐dioxabicyclo[3.2.1]‐octanes and functionalized cyclopentenoles from their common intermediate 1,5‐diketones and acetylene in the KOH/DMSO superbasic media is investigated using the B2PLYP/6‐311++G**//B3LYP/6‐31+G* calculations with particular attention to the diastereoselectivity aspects of individual stages.

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Section: Introductionmentioning

confidence: 99%

Two classes of heterocycles—6,8‐dioxabicyclo[3.2.1]octanes and cyclopentenols from the same reagents: A quantum‐chemical comparison of mechanism

Vitkovskaya

Orel

Кобычев

et al. 2018

Int J of Quantum Chemistry

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“…2 Bearing in mind the therapeutic value of compounds 34-36, we focused our attention on acetylenes 17, 28, and 37-42, which should allow easy access to the side chains present in carbapenem antibiotics, and to nitrones available from L-and D-arabinose, and 2-deoxy-D-ribose (Figure 7). [30][31][32] Several of our attempts to reproduce the published procedure 33 for the synthesis of sugar-derived cyclic nitrones did not lead to the desired products.…”

Section: Derived Nitrones Toward the Synthesis Of Carbapenemsmentioning

confidence: 99%

An Entry to the Carbapenem Antibiotic Scaffold via the Asymmetric Kinugasa Reaction

et al. 2012

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The copper(I)-mediated reaction between five-membered cyclic nitrones and terminal acetylenes, leading to the assembly of the basic skeleton of carbapenem antibiotics is described. The diastereoselectivity of this cycloaddition-rearrangement cascade, a process known as the Kinugasa reaction, with respect to the structure and configuration of both substrates, as well as the reaction conditions, are discussed. Application of the described methodology to sugar-derived nitrones offers an attractive entry toward thienamycin and related compounds.

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“…59 Apparently, N-MCT inhibits lytic KSHV DNA synthesis through its triphosphate metabolite produced in KSHV-infected cells expressing a virally encoded thymidine kinase. 59 Recently, a "greener" enantioselective synthesis of N-MCT from 2-deoxy-D-ribose has been reported 60 and a new MCT distinct from N-MCT, namely D-(+)-iso-MCT ( Fig. 3), has been described as a high-affinity substrate for HSV-1 thymidine kinase.…”

Section: North-methanocarbathymidine (N-mct)mentioning

confidence: 99%

“…Recently, a “greener” enantioselective synthesis of N ‐MCT from 2‐deoxy‐ d ‐ribose has been reported and a new MCT distinct from N ‐MCT, namely d ‐(+)‐ iso ‐MCT (Fig. ), has been described as a high‐affinity substrate for HSV‐1 thymidine kinase .…”

Section: North‐methanocarbathymidine (N‐mct)mentioning

confidence: 99%

Highlights in Antiviral Drug Research: Antivirals at the Horizon

Clercq

2012

Medicinal Research Reviews

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This review highlights ten "hot topics" in current antiviral research: (i) new nucleoside derivatives (i.e., PSI-352938) showing high potential as a direct antiviral against hepatitis C virus (HCV); (ii) cyclopropavir, which should be further pursued for treatment of human cytomegalovirus (HCMV) infections; (iii) North-methanocarbathymidine (N-MCT), with a N-locked conformation, showing promising activity against both α- and γ-herpesviruses; (iv) CMX001, an orally bioavailable prodrug of cidofovir with broad-spectrum activity against DNA viruses, including polyoma, adeno, herpes, and pox; (v) favipiravir, which is primarily pursued for the treatment of influenza virus infections, but also inhibits the replication of other RNA viruses, particularly (-)RNA viruses such as arena, bunya, and hanta; (vi) newly emerging antiarenaviral compounds which should be more effective (and less toxic) than the ubiquitously used ribavirin; (vii) antipicornavirus agents in clinical development (pleconaril, BTA-798, and V-073); (viii) natural products receiving increased attention as potential antiviral drugs; (ix) antivirals such as U0126 targeted at specific cellular kinase pathways [i.e., mitogen extracellular kinase (MEK)], showing activity against influenza and other viruses; and (x) two structurally unrelated compounds (i.e., LJ-001 and dUY11) with broad-spectrum activity against virtually all enveloped RNA and DNA viruses.

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A greener enantioselective synthesis of the antiviral agent North-methanocarbathymidine (N-MCT) from 2-deoxy-d-ribose

Cited by 20 publications

References 39 publications

Two classes of heterocycles—6,8‐dioxabicyclo[3.2.1]octanes and cyclopentenols from the same reagents: A quantum‐chemical comparison of mechanism

Two classes of heterocycles—6,8‐dioxabicyclo[3.2.1]octanes and cyclopentenols from the same reagents: A quantum‐chemical comparison of mechanism

An Entry to the Carbapenem Antibiotic Scaffold via the Asymmetric Kinugasa Reaction

Highlights in Antiviral Drug Research: Antivirals at the Horizon

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