Synthesis of 1-Demethyltoxoflavin (8-Demethylfervenulin)<sup>1</sup>

Liao, T. K.; Baiocchi, Fred; Cheng, C. C.

doi:10.1021/jo01341a061

Cited by 26 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fervenulin ( 1 ), known also as planomycin, is a yellow crystalline solid, which was previously isolated from S. fervens and S. rubrireticuli (Liao et al 1965). Fervenulin ( 1 ) has a broad range of biological activities, e.g., in vitro antibacterial, antifungal, antiparasitic, and antitumor properties (DeBoer et al 1960).…”

Section: Discussionmentioning

confidence: 99%

Nematicidal activity of fervenulin isolated from a nematicidal actinomycete, Streptomyces sp. CMU-MH021, on Meloidogyne incognita

Ruanpanun

Laatsch

Tangchitsomkid³

et al. 2010

World J Microbiol Biotechnol

View full text Add to dashboard Cite

An isolate of the actinomycete, Streptomyces sp. CMU-MH021 produced secondary metabolites that inhibited egg hatch and increased juvenile mortality of the root-knot nematode Meloidogyne incognita in vitro. 16S rDNA gene sequencing showed that the isolate sequence was 99% identical to Streptomyces roseoverticillatus. The culture filtrates form different culture media were tested for nematocidal activity. The maximal activity against M. incognita was obtained by using modified basal (MB) medium. The nematicidal assay-directed fractionation of the culture broth delivered fervenulin (1) and isocoumarin (2). Fervenulin, a low molecular weight compound, shows a broad range of biological activities. However, nematicidal activity of fervenulin was not previously reported. The nematicidal activity of fervenulin (1) was assessed using the broth microdilution technique. The lowest minimum inhibitory concentrations (MICs) of the compound against egg hatch of M. incognita was 30 μg/ml and juvenile mortality of M. incognita increasing was observed at 120 μg/ml. Moreover, at the concentration of 250 μg/ml fervenulin (1) showed killing effect on second-stage nematode juveniles of M. incognita up to 100% after incubation for 96 h. Isocoumarin (2), another bioactive compound produced by Streptomyces sp. CMU-MH021, showed weak nematicidal activity with M. incognita.

show abstract

Section: Discussionmentioning

confidence: 99%

Nematicidal activity of fervenulin isolated from a nematicidal actinomycete, Streptomyces sp. CMU-MH021, on Meloidogyne incognita

Ruanpanun

Laatsch

Tangchitsomkid³

et al. 2010

World J Microbiol Biotechnol

View full text Add to dashboard Cite

show abstract

“…1,2,4-Triazines have been identified in microbial natural products and pigments, suggesting that they are stable in physiological environments. [21][22][23] These motifs also react efficiently with electron-rich alkenes in IED-DA reactions. [24][25][26][27][28][29] Boger further showed that 1,2,3-triazines react with electron-rich dienophiles.…”

mentioning

confidence: 98%

“…To develop improved bioorthogonal IED-DA reactions, we were drawn to triazine scaffolds. 1,2,4-Triazines have been identified in microbial natural products and pigments, suggesting that they are stable in physiological environments. − These motifs also react efficiently with electron-rich alkenes in IED-DA reactions. − Boger further showed that 1,2,3-triazines react with electron-rich dienophiles . To compare the intrinsic DA reactivities of 1,2,3- and 1,2,4-triazines with that of 1,2,4,5-tetrazine, we evaluated the activation free energies for their reactions with ethylene by density functional theory (DFT) calculations (Figure A, Table S1).…”

mentioning

confidence: 99%

1,2,4-Triazines Are Versatile Bioorthogonal Reagents

Kamber¹,

Liang²,

et al. 2015

View full text Add to dashboard Cite

A new class of bioorthogonal reagents, 1,2,4-triazines, is described. These scaffolds are stable in biological media and capable of robust reactivity with trans-cyclooctene (TCO). The enhanced stability of the triazine scaffold enabled its direct use in recombinant protein production. The triazine-TCO reaction can also be used in tandem with other bioorthogonal cycloaddition reactions. These features fill current voids in the bioorthogonal toolkit.

show abstract

“…N-unsubstituted derivatives, 5,7-dioxo-3-methyl-5,6,7,8-tetrahydropyrimido [5,4-e]-as-triazine (V), was synthesized (Scheme I). Compound V is the 7-aza analog of 6-methyllumazine.6-9 Experimental Section1 23 2-Chloro-5-iiitropyrimidine,4 54-amino-2-chloro-5-nitropyrimidine,= 2-chloro-4-dimet.hylamino-6-methyl-5-nitropyrimidine,6 and 2-chloro-4-methoxypyrimidine7 were prepared by procedures described in the literature.…”

mentioning

confidence: 99%