2. review of literature -...
TRANSCRIPT
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2. REVIEW OF LITERATURE
Carbohydrates are the most abundant class of biomolecules, making up to 75%
of the biomass on Earth.1
They are used to store energy, but also perform other
important functions in the life.2 Recently, carbohydrates and their derivatives
have emerged as an important tool for stereo selective synthesis and as a chiral
pool for the design and synthesis of the bioactive molecules. They are also used
as chiral building blocks, precursors for drug synthesis and chiral catalysts in
asymmetric catalysis.3-8
The importance of carbohydrates in biological events, the
pace of development of carbohydrate based therapeutics has been relatively slow.
This is mainly due practical synthetic and analytical difficulty. Recent advances
in the field of carbohydrate synthesis, however, have demonstrated that many of
these problems can be circumvented, and evidence the importance of
carbohydrates as bioactive substances, with regard to antibacterial, antiviral,
antineoplastic, antiprotozoal, antifungal activity. 9-15
The Preceeding text gives an overview of the therapeutic activities of
carbohydrates. These carbohydrates are generally poly or oligomeric units and
have a direct relevance with their core structure, sequence diversity, branching, N
or O linkage and overall orientations of hydrophobic and hydrophilic groups
present in the macromolecules. The highly interesting research output in cell
biology, immunology and biochemistry have help in creating general awarness
that carbohydrates contain a considerable amount of regio- and stereochemical
information which nature employs in diverse selection and directed distribution
process in multicellular organism. The role of monosaccharide derivatives for
evoking a specific biological response depends on the number of hydrophobic
and hydrophilic groups present on the molecules, number of chiral centre and on
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the physico-chemical nature of the pharmacophore appendages to the
monosachharide. A survey of the literature indicates that only scanty information
exists about the therapeutic nature of monosaccharide in furanose form. During
initiation of present work it was, therefore, considered desirable to study the
therapeutic properties of furanose form of monosaccharide possessing appropriate
pharmacophores as appendages to the basic skeleton.
Figure 2.1: General Representation of Mannofuranoside and Glucofuranoside
Derivative
O
O O
O
O
O O
O
O
O
OO
Aglycon
Glycon: Mannofuranose Moiety
Aglycon
Glycon: Glucofuranose Moiety
2.1. D-Mannose:
D-mannose is a sugar monomer of the aldohexose series of carbohydrate.
D-mannose is a C-2 epimer of glucose. Mannose is important in human
metabolism, especially in the glycosylation of certain proteins. Several congenital
disorder of glycosylation are associated with mutation of enzymes involved in
mannose metabolism.16
2.1.1. Structure of D-Mannose:
Two of the cyclic mannose anomers possess a pyranose (six-membered)
ring, while the other two possess a furanose (five-membered) ring.
29
Figure 2.2: a; D-Mannose in Fischer projection b; α-D-mannopyranose c; β-D-
mannopyranose d; α-D-mannofuranose e; β-D-mannofuranose
O
OHOH
OH
CH2OH
O
OH
OH
CH2OH
OH
HHO
HHO
OHH
OHH
CH2OH
H
a
b c
OH
HO OH
O
H
HOHO
OH
HO OH
O
H
HOHO
d e
O
OH OH
2.1.2. Aglycon Moiety; Heterocycles:
Heterocycles form the largest group of organic chemistry and have immense
biological importance. For more than a century, heterocycles have constituted one
the largest areas of research in organic chemistry. The presence of heterocycles in
all kinds of organic compounds of interest biology and pharmacology is very well
known. Heteroatoms such as sulfur, nitrogen, oxygen and phosphorus containing
heterocyclic compounds17-19
have widespread therapeutic applications such as
antibacterial, antifungal, antimycobacterial, trypanocidal, anti-HIV activity,
30
antileishmanial agents, genotoxic, antitubercular, antimalarial, herbicidal,
analgesic, antiinflammatory, muscle relaxants anticonvulsant, anticancer and lipid
peroxidation inhibitor, hypnotics, antidepressant, antitumoral, anthelmintic and
insecticidal agents.20-25
Figure 2.3: Various Therapeutic Applications of Heterocyclic Moieties and its
Derivatives
Triazole and other heterocyclic moieties are under study since many years. Its
diversity showing the pharmacological activities is mind blowingly identified
well by the medicinal chemists.26
It shows various therapeutic activities such as
antiinflammatory27
, antimicrobials28
, β‐lactamase inhibitors29
, fungicidal30
,
insecticidal31
, antitumor32
, anticonvulsant33
, antidepressant34
, plant growth
inhibitor.35
Among various triazole and other heterocyclic derivatives, base and
Heterocycles
Antimicrobi
al activity
Antitumor
activity Antifungal
activity
Anti-
inflammatory
activity
Antiviral
activity
Anticonvulsant
activity
Antituberculor
activity
β‐lactamase
inhibitors
Plant growth
inhibitor
31
sugar modified nucleoside derivatives reflect a potent anti‐microbial activity
resulting in its application in the chemotherapy of cancer and viral infection.36
Coumarins occupy an important place in the realm of natural products and
synthetic organic chemistry.37,38
Coumarins comprise a group of natural
compounds found in a variety of plant sources in the form of benzopyrene
derivatives. Coumarins have important effects in plant biochemistry and
physiology, as they act as antioxidants, enzyme inhibitors, and precursors of toxic
substances. In addition, these compounds are involved in the form of plant
growth hormones and growth regulators, control of respiration, photosynthesis, as
well as defense against infections.39
Coumarins have long been recognized to
possess anti-inflammatory, anti-oxidant, anti-allergic, hepatoprotective, anti-
thrombotic, anti-viral and anti-carcinogenic activities.40-42
Hydroxycoumarins are
typical phenolic compounds and therefore, act as potential therapeutic agents
such as metal chelators, free radical scavengers and also extraordinary range of
biochemical and pharmacological activities of these chemicals in mammalian and
other biological systems.43,44
The coumarins are extremely variable in structure, due to the various types of
substitutions in their basic structure, which can influence their biological activity.
The interesting biological activities of the coumarins have made them attractive
targets in organic synthesis.
32
Figure 2.4: Various Therapeutic Applications of Coumarin and its Derivatives
In light of these interesting biological activities of heterocycles, it became
interested in synthesizing some new O-glycosides of substituted heterocyclic
derivatives and evaluating their antimicrobial potential.
2.1.3. O-Glycosylation of 2,3,5,6-bis-O-isopropylidene-α-D-mannofuranose
with Aglycon Moieties:
An efficient anomeric stereocontrolled glycosylation method, with high
yield of α-anomer, was reported recently by using O-glycosyl
trichloroacetamidate as a donor and alcohol as an acceptor in the presence of
catalytic amounts of TMSOTf as Lewis acid.45
Following this synthetic protocol,
2,3,5,6-di-O-isopropylidene-D-mannofuranose was prepared first by the reaction
of D-mannose with acetone in presence of catalytic amount of concentrated
sulfuric acid.46,47
This compound was selected as the glycosyl donor, was then
Coumarin &
its Derivatives
Anti-Inflammatory
Activity
Antibacterial &
Antiviral
Activity
Metal Chelators
Scavenger
Anticlotting &
Antithrombotic
Activity
Anticarcinogenic
Activity Hepatoprotective
Activity
Anti- HIV
Activity
33
coupled with alcohol acceptor of heterocyclic compounds to afford 1-O-(2-
methyl-1H-benzimidazol-1-ylmethyl)-2,3,5,6-di-O-isopropylidene-α-D-
mannofuranoside and 2-Benzothiazolylthioacetyl O-(2,3,5,6-bis-O-
isopropylidene-α-D-mannofuranosyl) L-serinemethyl ester in a good yield.
Figure 2.5: Coupling of 2,3,5,6-bis-O-isopropylidene-D-mannofuranose with
Aglycon moiety in Presence of Trimethylsilyl trifluoromethanesulfonate
(TMSOTf) and Dichloromethane48-50
O
O O
O
O
OH
+N
N
CH3
O
HN CCl3
TMSOTf
CH2Cl2
O
O O
O
O
ON
NH3C
OTMSOTf
CH2Cl2
O OO
O
O
NH
CCl3
N
S
S
O
NH
HO
O
OCH3+O
O OO
O
O
N
S
S
O
NH
O
OCH3
2.2. D-Glucose:
Glucose has 4 chiral centers. In theory, glucose may have 15 optical
stereoisomers. Only seven of them are found in living organisms. When glucose
is in its ring form, an additional asymmetric carbon, the anomeric carbon atom, is
created at C1. This leads to the formation of two ring structures (anomers), α-D-
Glucose and β-D-Glucose. In the form, the hydroxyl group attached to C-1 is
below the plane of the ring, in the β form it is above. The α and β forms
34
interconvert over a timescale of hours in aqueous solution, to a final stable ratio
of α:β 36:64, in a process called mutarotation.
2.2.1. Structure of D-Glucose:
Two of the cyclic glucose anomers possess a pyranose (six-membered)
ring, while the other two possess a furanose (five-membered) ring.
Figure 2.6`: a; D-Glucose in Fischer projection b; α-D-glucopyranose c; β-D-
glucopyranose d; α-D-glucofuranose e; β-D-glucofuranose
OH
OH
HO
O
H
HOHO
OH
OH
HO
O
H
HOHO
O
OH
OHOH
OH
CH2OH
O
OH
OH
OH
CH2OH
OH
OHH
HHO
OHH
OHH
CH2OH
OH
a
b c
d e
35
2.2.2. O-Glycosylation of 1,2,5,6-bis-O-isopropylidene-α-D-glucofuranose
with Aglycon Moieties:
Monosaccharides with good leaving groups like acylate, tosylate and
benzoate play a major role for the introduction of various functional groups, as
building blocks for the formation of di- and oligosaccharide, as chiral pool
materials or for the preparation of bioactive glycoconjugates.51-54
Alkyl and acyl
glycoses and glycoside derivatives of carbohydrates have immense importance
and some of them are biologically active.55
Protection of a particular functional
group of carbohydrates, especially monosaccharides, is not only necessary for the
modification of the remaining functional groups but also for the synthesis of
newer derivatives of great importance.56
Various methods for acylation of
carbohydrates and nucleosides have so far been developed and employed
successfully.57-59
A large number of biologically active compounds possess
aromatic and heteroaromatic nuclei. It is also known that if an active nucleus is
linked to another nucleus, the resulting nucleus may possess enhanced biological
activity.60
The benzene and substituted benzene nuclei play important role as
common denominator for various biological activities, which is also revealed by a
number of previous reports. For example, acylated n-butyl α- and β-D-
glucopyranoside were employed as test chemicals for in vitro antibacterial and
antifungal functionality test against various human pathogenic bacteria and fungi.
The study revealed that the tested n-butyl glucopyranoside derivatives showed
better antimicrobial functionalities as compared to the standard antibiotic.61
Similarly, a number of 2,3-di-O-acyl derivatives of methyl 4-O-acetyl-α-L-
rhamnopyranoside were screened against bacterial and fungal pathogens. The
study revealed that the acylated rhamnopyranoside derivatives are more prone
towards antifungal activities than that of antibacterial activities.62
Synthesis of
36
some acylated monosaccharide derivatives (e.g. D-glucose) in furanose and
pyranose form containing various acyl and aromatic moieties in a single
molecular framework and evaluated their comparative antimicrobial activities
using a variety of bacterial and fungal pathogens.
Figure 2.7: Methyl 4,6-O-benzylidene-α-D-glucopyranoside, Methyl 4,6-O-
benzylidene-α-D-mannopyranoside and a Number of its Derivatives were
Screened for in vitro Antibacterial and Antifugal Activity Against Various
Bacterial and Fungal Strains 63-66
O
R1O
OMe
OR
O
O
Ph
O
RO
OMe
O
O
Ph
OR1
a b
R = R1 = H R = R1 = H
R = Stearoyl, R1 = H R = 4-Cl, Bz; R1 = Ac
R = Stearoyl, R1 = Ac R = 4-Cl, Bz; R1 = Bz
R = Stearoyl, R1 = Bz R = 4-Cl, Bz; R1 = Octanoyl
R = Stearoyl, R1 = pTs R = 4-Cl, Bz; R1 = Decanoyl
Mono-substituted mannofuranose and glucofuranose derivatives were
investigated for their antimicrobial activity against a range of pathogenic bacteria
and fungi.
37
Figure 2.8: Some Acylated Derivatives of benzyl 2,3-O-isopropylidene-α-D-
mannofuranoside and 1,2,5,6-d-O-isopropylidene-α-D-glucofuranose Investigated
for in vitro Antimicrobial Activity Against Various Strains67,68
O
O
O
O
OOR
O
O O
R2O
R1O
OBn
cd
R1 = H; R2 = H R = H
R1 = Myr; R2 = H R = Ms
R1 = Myr; R2 = Ac R = Laur
R1 = Myr; R2 = Bz
Carbohydrate fatty acid ether and esters are another class of fatty acid derivatives
shown a significant activity, and they have broad applications in the food
industry.69-71
They are most commonly employed as surfactants, their
antimicrobial properties have been reported. The use of carbohydrate esters is
continually increasing as they are completely biodegradable, they are not harmful
to the environment and they are non-toxic.72
Another attractive feature of
carbohydrate fatty acid derivatives is the potential to modify their properties by
controlling the degree of substitution of the carbohydrate, by varying the nature
of the fatty acid and also the sugar itself. They are currently being employed in
38
the food, cosmetic and detergent industry.73
Sugar esters are widely used in Japan
as antibacterial agents in canned drinks.
Figure 2.9: Synthesis of Ether and Ester Carbohydrate Derivatives74,75
O
O
O
O
OOH
DMF anhydrous
1-chlorododecaneNaH, 0°C-RT
O
O
O
O
OO
C11H23
O
O
O
O
OOH
Py. anhydrous
DMAP, LauroylChloride, RT
O
O
O
O
OO
C11H23
O
The primary screening of synthesized compounds was done by well diffusion
method. Antimicrobial efficacy of the synthesized compounds was compared
with commercially available compounds such as Ampicillin and fluconazole
which have proven antimicrobial activity. Compounds efficacy was compared
using an absorbance based broth micro dilution assay to determine the Inhibitory
Concentration (IC50).76-85
39
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