“…These papers revealed the important medicinal and biological applications of such compounds. 7,8-DHISQ's are potent inhibitors of Lck [19] and intermediates for synthesis of mimosamycin [20]. 7,8-DHISQ's are synthesized from 5,6,7,8-tetrahydroisoquinoline (5,6,7,8-THISQ's) through functionalization of C-5 by introducing an alcoholic group followed by elimination of water molecule from C-5 and C-6 to afford the desired products via four steps [21].…”
Section: Introductionmentioning
confidence: 99%
“…In addition, the yield of this method is low and the used reagents are hazard. Also, 7,8-DHISQ's may be synthesized in the form of 7,8-dione by starting with 7-methoxy-6-methylisoquinoline [20,22]. 7,8-DHISQ's were synthesized via metabolites of 5,6,7,8-THISQ's by Pseudomonas Putida UV4 [23] or metabolites of isoquinoline itself by Escherichia coli [11].…”
Ketonic hydrolysis of 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-phenyl-5,6,7,8-tetrahydro-isoquinoline-3(2H)-thione (1) via heating with aqueous solution of potassium hydroxide resulted in both deacetylation and dehydration affording new 7,8-dihydroisoquinoline scaffold (7,8-DHISQ) 2. Two simple mechanistic approaches are postulated for this synthesis. One of them was supported by converting 7-acetyl-4-cyano-1,6-dimethyl-8-phenyl-7,8-dihydroisoquinoline-3(2H)-thione (3) into 7,8-DHISQ 2 via heating with aqueous solution of potassium hydroxide. Compound 2 was used as a key intetermediate
“…These papers revealed the important medicinal and biological applications of such compounds. 7,8-DHISQ's are potent inhibitors of Lck [19] and intermediates for synthesis of mimosamycin [20]. 7,8-DHISQ's are synthesized from 5,6,7,8-tetrahydroisoquinoline (5,6,7,8-THISQ's) through functionalization of C-5 by introducing an alcoholic group followed by elimination of water molecule from C-5 and C-6 to afford the desired products via four steps [21].…”
Section: Introductionmentioning
confidence: 99%
“…In addition, the yield of this method is low and the used reagents are hazard. Also, 7,8-DHISQ's may be synthesized in the form of 7,8-dione by starting with 7-methoxy-6-methylisoquinoline [20,22]. 7,8-DHISQ's were synthesized via metabolites of 5,6,7,8-THISQ's by Pseudomonas Putida UV4 [23] or metabolites of isoquinoline itself by Escherichia coli [11].…”
Ketonic hydrolysis of 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-phenyl-5,6,7,8-tetrahydro-isoquinoline-3(2H)-thione (1) via heating with aqueous solution of potassium hydroxide resulted in both deacetylation and dehydration affording new 7,8-dihydroisoquinoline scaffold (7,8-DHISQ) 2. Two simple mechanistic approaches are postulated for this synthesis. One of them was supported by converting 7-acetyl-4-cyano-1,6-dimethyl-8-phenyl-7,8-dihydroisoquinoline-3(2H)-thione (3) into 7,8-DHISQ 2 via heating with aqueous solution of potassium hydroxide. Compound 2 was used as a key intetermediate
“…Compounds 2 and 3 have been previously isolated from sponges of the genus Reniera , but not from the genus Xestospongia, while compound 4 was reported to occur in blue sponges of both genera, Reniera and Xestospongia. Compound 4 is a known metabolite of the terrestial bacterium Streptomyces lavendulae, and it has previously been speculated , that a similar bacterium is epiphytic or symbiotic with the marine sponges. …”
An undescribed Philippine marine sponge of the genus
Xestospongia afforded four isoquinoline
quinones: the new N-ethylene methyl ketone derivative of
renierone (1), as well as the known
compounds 1,6-dimethyl-7-methoxy-5,8-dihydroisoquinoline-5,8-dione
(2), renierone (3), and
mimosamycin (4). Compound 2 exhibited
insecticidal activity toward neonate larvae of the
polyphagous pest insect Spodoptera littoralis
(EC50 of 35 ppm and LC50 of 521 ppm)
when
incorporated into artificial diet. Compounds 1 and
3 were only weakly active toward S.
littoralis,
while compound 4 was found to be inactive. All four
isolated compounds were active against
the Gram-positive bacteria Bacillus subtilis and
Staphyloccoccus aureus. Compound 4
was
also active against the fungus Cladosporium
cucumerinum.
“…The isoquinoline and quinone features of perfragilins A and B are reminiscent of mimosamycin [3] (6,7). However, the thiomethyl ether substituents render 1 and 2 quite unique.…”
mentioning
confidence: 99%
“…However, the thiomethyl ether substituents render 1 and 2 quite unique. Mimosamycin was reported initially (6,7) from the actinomycete Streptomyces lavendulae of terrestrial origin and more recently from several sponges, a Reneira sp. (8,9), Xestospongia caycedoi (10), Xestospongia sp.…”
Detailed spectroscopic and cytotoxicity data are reported for two new isoquinolinequinones, perfragilins A [1] and B [2], which were isolated from the bryozoan Membranipora perfragilis collected in South Australia. Both compounds, which are speculated to be of microbial origin, contain a relatively uncommon thiomethyl ether functionality.
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