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Synthesis
- Dragmacidin D is a potent inhibitor of serinethreonine protein
phosphatases (PP), and preliminary evidence suggests that dragmacidin D
is a selective inhibitor of PP1 versus PP2A.3b. The dragmacidins are an
emerging class of bis(indole) natural products isolated from deep-water
marine organisms.
- Although there has been a substantial effort to prepare the simple
piperazine dragmacidins, little synthetic work has been done in the area
of the pyrazinone-containing family members, dragmacidins D, E, and F.
These compounds are particularly interesting due to their complex
structures and broad range of biological activity. Of the possible
biosynthetic scenarios, most probable is that dragmacidins E and F
are derived by cyclization of either dragmacidin D or a closely
related congener
Cultivation
- Sponges are the most primitive of multicellular animals, and
are major pharmaceutical sources of marine secondary metabolites. A wide
variety of new compounds have been isolated from sponges. In order to
produce sufficient amounts of the compounds of the needed, it is
necessary to obtain large amount of sponges. The production of sponge
biomass has become a focus of marine biotechnology.
- The whole sponge body is designed for efficient filtration of the
surrounding seawater (Fig. 2A), which is essential because of the low
nutrient availability at the sea floor. Water is pumped into the sponge
via many small canals that start at the outer surface of the sponge. The
water current into the sponge is generated by specialised flagellated
cells, called choanocytes, which are clustered in choanocyte chambers in
the interior of the sponge
Application
& Technology
- The
indolylboronic acid 104 is obtained after 3-mercuriation of the
bromoindole 103, being employed for a double coupling to
2,5-dibromopyrazine giving compound 105 in a formal total synthesis
of dragmacidin B, trans-dragmacidin C and cis and trans-dihydrohamacanthins
A.211.
- An
enantiodivergent strategy for the total chemical synthesis of both
(+)- and (-)-dragmacidin F beginning from a single enantiomer of
quinic acid has been developed and successfully implemented.
Although unique, the synthetic routes to these antipodes share a
number of key features, including novel reductive isomerization
reactions, Pd(II)-mediated oxidative carbocyclization reactions,
halogen-selective Suzuki couplings, and high-yielding late-stage
Neber rearrangements
Market &
Report
- Some marine
sponges, for example, are a source of dragmacidins, a recently
discovered class of alkaloids that perform a wide range of
biological and pharmacological activities. Some Students were
experimenting with several kinds of sponges in an e ort to discover
new dragmacidins and determine their chemical structures.
- During 1998
research on the pharmacology of marine chemicals included in this
review involved investigators from 22 countries. This review
attempts to classify 59 peer-reviewed articles on the basis of the
reported preclinical pharmacological properties of marine chemicals
derived from a diverse group of marine animals, algae, fungi and
bacteria.
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