The synthesis of metacycloprodigionsin

Wasserman, Harry H.; Keith, Dennis D.; Nadelson, Jeffrey

doi:10.1016/0040-4020(76)85188-5

Cited by 29 publications

(21 citation statements)

References 18 publications

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“…12 Acid-catalyzed condensation of an appropriate alkyl pyrrole segments (2,4-dimethyl pyrrole, 6a-h , and 10a-k ) with 13-17 (Scheme 4) 13 gave the desired prodiginine analogs 18-25 (Table 1) and 26-43 (Table 2 and 3). …”

Section: Resultsmentioning

confidence: 99%

Antimalarial Activity of Natural and Synthetic Prodiginines

et al. 2011

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Prodiginines are a family of linear and cyclic oligopyrrole red-pigmented compounds. Herein we describe the in vitro antimalarial activity of 4 natural (IC50 = 1.7-8.0 nM) and 3 sets of synthetic prodiginines against Plasmodium falciparum. Set 1 compounds replaced the terminal non-alkylated pyrrole ring of natural prodiginines and had diminished activity (IC50 >2920 nM). Set 2 and set 3 prodiginines were monosubstituted or disubstituted at either the 3 or 5 position of the right hand terminal pyrrole, respectively. Potent in vitro activity (IC50 = 0.9-16.0 nM) was observed using alkyl or aryl substituents. Metacycloprodiginine and more potent synthetic analogs were evaluated in a P. yoelii murine patent infection using oral administration. Each analog reduced parasitemia by more than 90% after 25 mg/kg/day dosing, and in some cases provided a cure. The most favorable profile was 92% parasite reduction at 5 mg/kg/day, and 100% reduction at 25 mg/kg/day without any evident weight loses or clinical overt toxicity.

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Section: Resultsmentioning

confidence: 99%

Antimalarial Activity of Natural and Synthetic Prodiginines

et al. 2011

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“…Reduction of this putative structure over Pd/C and subsequent exposure to ammonium acetate (NH 4 OAc) gave rise to a material whose NMR spectra were different from those reported for the Wasserman pyrrole 5 . 4,6,7 Most puzzling was the missing diagnostic signal at −1.88 ppm in the 1 H NMR spectrum of our isolated material, which within 5 is attributed to an anisotropic shielding of the saturated hydrocarbon ring by the meta-fused pyrrole. This analysis, in conjunction with mass spectral data, led us to conclude that the ring-closing metathesis of 14 was probably generating dimeric structures instead of the more strained 12-membered ring.…”

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confidence: 87%

“…4 In the following journal article, they also reported the first total synthesis of racemic metacycloprodigiosin ( 1 ) by a 14-step route that involved the late-stage union of pyrrole 5 (i.e., the “Wasserman pyrrole”) with bis-pyrrole aldehyde 6 . 6 Fürstner and his group reported the second synthesis of the racemate via 5 in a formal sense in 1998 (10-steps), and again in 1999 (20-steps, also via 5 ). 7 …”

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confidence: 99%

Enantioselective synthesis of metacycloprodigiosin via the ‘Wasserman pyrrole’

Vega

Crain

Konkol

et al. 2015

Tetrahedron Letters

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A concise, nine-step enantioselective total synthesis of metacycloprodigiosin is reported. The synthesis provides increased step-efficiency over the previous racemic and enantioselective syntheses of this compound. Key features of the work include investigations into a convergent oxidative coupling reaction and subsequent ring-closing metathesis to deliver an advanced pyrrole intermediate we name the “Wasserman pyrrole” that can be converted to metacycloprodigiosin in one step.

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“…Although their synthetic history is long (71)(72)(73)(74), a simple and elegant way to synthesize prodigiosins was reported recently (75) which will help in the synthesis of new active derivatives.…”

Section: Prodigiosins As New Hmentioning

confidence: 99%

Prodigiosins as a New Group of H+/Cl−Symporters That Uncouple Proton Translocators

Satō¹,

Konno²,

Tanaka³

et al. 1998

Journal of Biological Chemistry

158

113

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We reported previously (Kataoka, T., Muroi, M., Ohkuma, S., Waritani, T., Magae, J., Takatsuki /Cl؊ symport (or OH ؊ /Cl ؊ exchange, in its equivalence) across vesicular membranes. In fact, prodigiosins displayed H ؉ /Cl ؊ symport activity on liposomal membranes. First of all, they decreased the internal pH of liposomes depending on the external chloride, and raised it depending on the internal chloride when external buffer was free from chloride. Second, their effect was electroneutral and not seriously affected by the application of an inside positive membrane potential generated by K ؉ and valinomycin. Finally, they promoted the uptake of [ 36 Cl] from external buffers with concomitant intraliposomal acidification when external pH was acidic relative to liposome interior. As prodigiosins hardly inhibit the catalytic activity (ATP hydrolysis) unlike well known OH ؊ /Cl ؊ exchangers (for example, tributyltin chloride), they should provide powerful tools for the study of molecular machinery and cellular activities involving transport of protons and/or chloride.

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The synthesis of metacycloprodigionsin

Cited by 29 publications

References 18 publications

Antimalarial Activity of Natural and Synthetic Prodiginines

Antimalarial Activity of Natural and Synthetic Prodiginines

Enantioselective synthesis of metacycloprodigiosin via the ‘Wasserman pyrrole’

Prodigiosins as a New Group of H+/Cl−Symporters That Uncouple Proton Translocators

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