Three differently substituted naturally occurring, biologically active carbazole derivatives viz. ekeberginine, murrayaquinone A and glycozoline were synthesized in good yield using short and simple routes. Prenyl group was selectively introduced at C4 position using Stille coupling reaction in the synthesis of ekeberginine. Murrayaquinone A was synthesized using Raney nickel mediated desulfurization of dithiane as a key step.Synthesis of glycozoline was achieved in two steps from 3-methyl carbazole via an intermediate 3-bromo-6-methyl carbazole.
Two new, efficient and simple routes using Heck-type reaction and intramolecular cyclization were developed for the synthesis of the naturally occurring cytotoxic alkaloid 2-(4-oxo-3,4-dihydroquinazolin-2-yl)-1H-indole-3-carbaldehyde (bouchardatine).
In
this study, a siderophore, pyoverdine (PVD), has been isolated
from Pseudomonas sp. and used to develop a fluorescence quenching-based
sensor for efficient detection of nitrotriazolone (NTO) in aqueous
media, in contrast to other explosives such as research department
explosive (RDX), picric acid, and trinitrotoulene (TNT). The siderophore
PVD exhibited enhanced fluorescence quenching above 50% at 470 nm
for a minimal concentration (38 nM) of NTO. The limit of detection
estimated from interpolating the graph of fluorescence intensity (at
470 nm) versus NTO concentration is found to be 12 nM corresponding
to 18% quenching. The time delay fluorescence spectroscopy of the
PVD–NTO solution showed a negligible change of 0.09 ns between
the minimum and maximum NTO concentrations. The in silico absorption
at the emission peak of static fluorescence remains invariant upon
the addition of NTO. The computational studies revealed the formation
of inter- and intramolecular hydrogen-bonding interactions between
the energetically stable complexes of PVD and NTO. Although the analysis
of Stern–Volmer plots and computational studies imply that
the quenching mechanism is a combination of both dynamic and static
quenching, the latter is dominant over the earlier. The static quenching
is attributed to ground-state complex formation, as supported by the
computational analysis.
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