Production, isolation and chemical characterization of mimosamycin.

Fukumi, Hiroshi; Maruyama, Fumio; Yoshida, Kayoko; Arai, Mamoru; Kubo, Akinori; Arai, Tadashi

doi:10.7164/antibiotics.31.847

Cited by 10 publications

(5 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…MS m / z (%): 233 (M + , 100), 218 (82), 205 (72), 190 (47), 162 (32), 134 (33). The analytical and spectral data are in accordance with those of the natural mimosamycin as published in the literature 1c…”

Section: Methodssupporting

confidence: 84%

“…The combined organic extracts were stirred with potassium carbonate (1 g) for 1 h, filtered, and evaporated in vacuo. Recrystallization from ethyl acetate gave mimosamycin as yellow needles, mp 228.5−229 °C (lit 1a. mp 219−231 °C).…”

Section: Methodsmentioning

confidence: 99%

“…Mimosamycin ( 1 ) (7-methoxy-2,6-dimethyl-3,5,8(2 H )-isoquinolinetrione) was the first member of a new class of naturally occurring 3,5,8(2 H )-isoquinolinetrione antibiotics, isolated as a satellite metabolite from the streptothricin-producing microorganism Streptomyces lavendulae No. 314 . Later, mimosamycin together with several structurally related pigments, e.g., 4-aminomimosamycin ( 2 ), 7-amino-7-demethoxymimosamycin ( 3 ), and the sulfur-containing perfragillin ( 4 ), have been identified in marine sponges of the genera Reniera , Petrosia , Xestospongia, and in the bryozoan Membranipora perfragilis …”

Section: Introductionmentioning

confidence: 99%

“…Mimosamycin has been found to be active against mainly mycobacteria, including the streptomycin-resistant strains of Mycobacterium tuberculosis . Furthermore, mimosamycin proved to be active against some Gram-positive bacteria, but it was completely inactive against Gram-negative bacteria and most fungi 1 except Cladosporium cucumerinum . Mimosamycin is also structurally related to the saframycins, which represent a more complex class of “dimeric” isoquinoline quinones with antitumor activity .…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Mimosamycin

Kesteleyn

Kimpe

2000

J. Org. Chem.

View full text Add to dashboard Cite

Mimosamycin (1) was synthesized in eight steps with an overall yield of 13% from 2-methoxy-3-methyl-1,4-benzoquinone by regioselective introduction of a chloromethyl group at C-6 and a methoxycarbonylmethyl group at C-5 and subsequent reaction of the intermediate methyl (o-(chloromethyl)phenyl)acetate derivative 16 with methylamine. Oxidation of the 5,7,8-trimethoxy-2,6-dimethyl-1, 4-dihydroisoquinoline-3(2H)-one 17 thus obtained, using cerium(IV) ammonium nitrate as a selective oxidizing agent, gave mimosamycin (1) in good overall yield.

show abstract

Section: Methodssupporting

confidence: 84%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Mimosamycin

Kesteleyn

Kimpe

2000

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…4 erwies sich im sauren wie im alkalischen Bereich gegenuber Luftoxidation stabil. Wir haben unseren Strukturvorschlag anhand einer Modellsubstanz dem einfach zuganglichen (5-Hydroxy-2-methylisochinolinium)methylsulfat (5) uberpruft. 5 wird aus dem kauflichen 5-Hydroxyisochinolin durch Methylierung mittels Dimethylsulfat erhalten.…”

unclassified