Structure determination of purpuromycin, a new antibiotic

Bardone, M. R.; Martinelli, E.; Zerilli, L. F.; Coronelli, C.

doi:10.1016/s0040-4020(01)97439-3

Cited by 60 publications

(27 citation statements)

References 7 publications

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“…Structurally related to the rubromycins are purpuromycin, [4] the griseorhodins, [5Ϫ9] the DK-7814 compounds, [10] and heliquinomycin (1, see Figure 1), [11] all of which are isolated from actinomycetes. The numerous structural investigations on these dyes were followed by detailed work on the mode of action, [12Ϫ14] the chemical reactivity, [15] the biosynthesis, [3,16] and the total synthesis [17] of selected representatives of this so-called rubromycin group of antibiotics.…”

Section: Introductionmentioning

confidence: 99%

Determination of the Absolute Configurations of γ-Rubromycin and Related Spiro Compounds by Quantum Chemical CD Calculations

et al. 2000

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The absolute configurations of the spiro compounds γ-and β-rubromycin (2 and 3), natural antibiotics derived from actinomycetes, have been elucidated as (S) by quantum chemical calculations of their chiroptical properties and comparisons with the respective experimental CD spectra. Surprisingly, their spiro centers show an absolute configuration opposite to that of heliquinomycin (1), the only related spiro compound for which the configuration has hitherto been as-

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Section: Introductionmentioning

confidence: 99%

Determination of the Absolute Configurations of γ-Rubromycin and Related Spiro Compounds by Quantum Chemical CD Calculations

et al. 2000

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“…[4][5][6][7] a-Rubromycin (3), the only member of the group to lack the aryl spiroketal moiety, exhibits substantially decreased inhibitory potency towards telomerase (IC 50 > 200 mm), which suggests that the spiroketal core is an essential pharmacophore for the inhibition of telomerase. [4] Purpuromycin (4), [8] a potential topical agent for vaginal infections, [2] and heliquinomycin (5), a selective inhibitor of DNA helicase are structurally related to the rubromycins. [6] Thus, 56 years since the isolation of 1, the rubromycins still attract considerable synthetic efforts because of their unprecedented structures and intriguing pharmacological profile.…”

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confidence: 99%

An Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)‐γ‐Rubromycin

et al. 2009

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Balancing act: The correct balance of electronic factors in the naphthazarin and isocoumarin fragments facilitates the acid‐mediated spiroketalization step to afford the key densely functionalized spiroketal (see picture; EOM=ethoxymethyl) in the formal synthesis of (±)‐γ‐rubromycin. A novel regioselective allyloxylation/Claisen rearrangement of 2‐azido‐1,4‐naphthoquinone provides access to the highly oxygenated naphthazarin fragment.

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“…α‐Rubromycin ( 3 ), the only member of the group to lack the aryl spiroketal moiety, exhibits substantially decreased inhibitory potency towards telomerase (IC 50 >200 μ M ), which suggests that the spiroketal core is an essential pharmacophore for the inhibition of telomerase 4. Purpuromycin ( 4 ),8 a potential topical agent for vaginal infections,2 and heliquinomycin ( 5 ), a selective inhibitor of DNA helicase are structurally related to the rubromycins 6. Thus, 56 years since the isolation of 1 , the rubromycins still attract considerable synthetic efforts because of their unprecedented structures and intriguing pharmacological profile 5.…”

Section: Methodsmentioning

confidence: 99%

An Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)‐γ‐Rubromycin

Rathwell¹,

Yang²,

Tsang³

et al. 2009

Angewandte Chemie

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Balanceakt: Das Gleichgewicht der elektronischen Faktoren im Naphthazarin‐ und Isocumarin‐Fragment erleichtert die säurevermittelte Cyclisierung zum dicht funktionalisierten Spiroketal (siehe Bild; EOM=Ethoxymethyl) in einer formalen Synthese von (±)‐γ‐Rubromycin. Eine Sequenz aus regioselektiver Allyloxylierung und Claisen‐Umlagerung macht das hoch oxygenierte Naphthazarin‐Fragment ausgehend von 2‐Azido‐1,4‐naphthochinon zugänglich.

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Structure determination of purpuromycin, a new antibiotic

Cited by 60 publications

References 7 publications

Determination of the Absolute Configurations of γ-Rubromycin and Related Spiro Compounds by Quantum Chemical CD Calculations

Determination of the Absolute Configurations of γ-Rubromycin and Related Spiro Compounds by Quantum Chemical CD Calculations

An Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)‐γ‐Rubromycin

An Efficient Formal Synthesis of the Human Telomerase Inhibitor (±)‐γ‐Rubromycin

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