Neplanocin A. A cyclopentenyl analog of adenosine with specificity for inhibiting RNA methylation.

Glazer, Robert I.; Knode, Marian C.

doi:10.1016/s0021-9258(18)90641-1

Cited by 74 publications

(11 citation statements)

References 12 publications

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“…studies have been performed in which the unique activity of this substance has been confirmed. [9][10][11][12][13][14][15][16][17][18][19][20][21] Moreover, the incorporation of the same unsaturated carbocyclic "sugar" has been extended to other non-naturally occurring carbocyclic nucleosides with similar results in terms of pharmacological selectivity and potency.14,22-28…”

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confidence: 99%

“…Our strategy was conceptually different from that of Ohno et al in that we utilized a chiral carbohydrate precursor to gain control of the three stereochemical centers of the molecule. The success of our approach hinged upon an efficient synthesis of 10a, from either D-ribose or the protected D-ribonic acid lactone (9), from which the cyclopentenylamine 4 was to be stereoselectively generated (Scheme I).…”

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confidence: 99%

“…9 g of crystalline material. This material was recrystallized from a mixture of ethyl acetate and petroleum ether (1:2) to give Caled for C^H^CINA: C, 59.62; H, 5.76; Cl, 8.80; N, 13.91.Found: C, 59.42; H, 5.75; Cl, 8.87; N,14.02.…”

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confidence: 99%

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Total synthesis of (-)-neplanocin A

Márquez¹,

Lim²,

Tseng³

et al. 1988

J. Org. Chem.

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Total synthesis of (-)-neplanocin A

Márquez¹,

Lim²,

Tseng³

et al. 1988

J. Org. Chem.

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“…We have isolated a variety of antiinsectan metabolites from sclerotia of Aspergillus spp. 2,3,6 In some cases, these compounds are found only in the sclerotia. 3,6 We recently reported four new indole diterpenoids (e.g.…”

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confidence: 99%

Sulpinines A-C and secopenitrem B: new antiinsectan metabolites from the sclerotia of Aspergillus sulphureus

Laakso¹,

Gloer²,

Wicklow³

et al. 1992

J. Org. Chem.

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Extracts from the sclerotia of Aspergillus sulphureus have yielded four new antiinsectan compounds of the paspaline/penitrem class (2-6). These metabolites were isolated by a combination of chromatographic techniques. The structures were determined primarily by analysis of various NMR experiments and also by comparison to the structurally related penitrems. Sulpinine C contains an unusual eight-membered-ring lactam and possesses a ring system previously unreported as part of a natural product. The three indole metabolites (2,3, and 5) exhibit potent activity against the lepidopteran crop pest Helicoverpa zea.Fungal bodies called sclerotia are produced by many species of fungi. These propagules are resistant to extremes of temperature, desiccation, and nutrient poor conditions and therefore foster the long-term survival of the fungal Because these structures may remain dormant in the soil for years, they may be exposed to a variety of fungivorous i n~e c t s .~?~ Some flowering plants allocate defensive substances preferentially to metabolically costly but reproductively significant structures (i.e. seed^).^ By analogy to seeds, sclerotia may also possess defensive compounds not found in the fungal mycelium.We have isolated a variety of antiinsectan metabolites from sclerotia of Aspergillus spp.2i3*6 In some cases, these compounds are found only in the ~clerotia.~*~ We recently reported four new indole diterpenoids (e.g. radarin A; 1) from the sclerotia of Aspergillus sulphureus (Fres.) Thom and Church (NRRL 4077).7 Four additional new antiinsectan metabolites, sulpinines A-C (2-4) and secopenitrem B (5), as well as the known Penicillium metabolite penitrem B (6) have now been isolated from A. sulphureus. Details of the isolation and characterization of 2-5 are presented here. Sclerotia from A. sulphureus were produced by solid substrate fermentation on corn kerneh2 The methylene chloride extract of the harvested, ground sclerotia possessed exceptional antiinsectan activity against the agriculturally important lepidopteran Helicouerpa zea. This extract was fractionated by silica gel column chromatography. All five compounds described here were found within a distinct red band that eluted first from the column using increasing concentrations of methanol in chloroform up to 4%. Although this fraction was complex, the mixture could be separated directly into pure compounds by reversed-phase HPLC.The major component of this fraction, sulpinine A (2), exerted potent effects on H. zea. The molecular formula (1) Willeta, H. J. Biol. Rev. Cambridge Philos. SOC. 1971, 46, 387. (2) Wicklow, D. T.; Dowd, P. F.; TePaske, M. R.; Gloer, J. B. Tram. (3) Gloer, J. B.; TePaske, M. R.; Sima, J.; Wicklow, D. T.; Dowd, P. (4) Wicklow, D. T.; Cole, R.was determined to be C32H41N04 by analysis of 13C NMR and HREIMS data. The 'H NMR spectrum and homonuclear decoupling experiments revealed the presence of a 1,2,4trisubstituted benzene ring, an isoprene unit, and a series of four downfield-shifted proton signals in the region from 3.4 to ...

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“…For 24b: NMR (CDC13) 0.88 (br t, J = 6.0 Hz, 3 H, CH2CH3), 1.27 (br s, 14 H, (CH2)7CH3), 1.42 (s, 9 H, t-Bu), 1.59-1.97 (m, 2 H, S(0)CH2CH2), 2.77 (d oft ,J = 8.0 Hz, 2 H, S(0)CH2CH2), 2.89-3.21 (AB part of ABX spectrum, 7 lines, 2 H, CHCH2S(0)), 3.47 (br t, J = 6.0 Hz, 1 H, CH2OH), 3.64-3.99 (AB part of ABX spectrum, 8 lines, 2 H, CHCH2OH), 3.89-4.26 (m, 1 H, CHCH2OH), 5.50 (br d, 1 H, NH). Anal.…”

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Comparison of aminoglycoside antibiotics with respect to uptake and lethal activity in Escherichia coli

Allen¹,

Alborn²,

Kirst³

et al. 1987

J. Med. Chem.

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Forty-five aminoglycoside antibiotics and related compounds were compared for their ability to induce the accumulation of dihydrostreptomycin in Escherichia coli K12. The common aminoglycosides and a streptothricin antibiotic all induced enhanced uptake within a relatively narrow concentration range. These concentrations were lethal to the bacteria. Comparison of aminoacyl derivatives of tobramycin and apramycin, the latter synthesized utilizing transition-metal cations to selectively control the site of substitution, revealed that 1-N-aminoacyl modifications resulted in an increased ability to induce enhanced uptake. 2'-N-Aminoacyl modifications were also effective at inducing enhanced uptake, albeit without noticeable improvement over parent. The findings from this structure-activity comparison support the proposition that aminoglycosides share a common critical target (most likely the ribosome), which, when acted upon, results in both drug accumulation and killing.

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Neplanocin A. A cyclopentenyl analog of adenosine with specificity for inhibiting RNA methylation.

Cited by 74 publications

References 12 publications

Total synthesis of (-)-neplanocin A

Total synthesis of (-)-neplanocin A

Sulpinines A-C and secopenitrem B: new antiinsectan metabolites from the sclerotia of Aspergillus sulphureus

Comparison of aminoglycoside antibiotics with respect to uptake and lethal activity in Escherichia coli

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