bioactive flavonoids of therapeutic importance
R.B.Kshatriyaa, Dr.G.M.Nazeruddin
1. Poona College, Pune 2.T.C. College, Baramati (University Of Pune, Pune), India.
Email: rbkpgadm@gmail.com,gmnazeruddin@yahoo.com
KEYWORDS: Orthohydroxy Acetophenones, chalcones, flavone, flavanones etc.
INTRODUCTION: Flavonoids are naturally occurring compounds as secondary metabolites inplants functions as physiological survival of plant from by protecting it from fungal infections
and UV radiations. In addition involved in photosensitisation, energy transfer,
photosynthesis, respiration, and morphogenesis and sex determination. They contains C6C3-C6 skeleton with two oxygen atoms. The shikimic acid pathway is a major route for thesynthesis of aromatic compounds in plants and microorganisms including protinaceous
amino acids phenylalanine, tyrosine and tryptophan. Flavonoids are synthesised via
phenylpropanoid pathway. Phenylalanine, tyrosine and tryptophan are the primarymetabolites, which serve as a precursor for many natural (secondary) products such as
flavonoids, phenolic acids, Coumarins, alkaloids, glycosilonates and cynogenic glycosides.
Most secondary metabolites with diverse antibiotic activity were synthesised through theshikimic acid pathway. Although melanic acid pathway is also involved in the biosynthesis ofsome of these compounds (flavonoids).The first key step in the shikimic acid pathway s
condensation of erythrose-4-phosphate from pentose phosphate pathway. Phenylalanine
ammonia lyase is the important enzyme in the synthesis of flavonoid compounds.
Flavonoids are classifieds a Flavone, flavanone, flavonol, Flavane, iso and neo of the same,
anthocynidine and bioflavonoid. Flavonoids are used in the areas of infectious diseases
including resistant bacterial infections, tuberculosis, opportunistic infections, viralinfections, fungal infections, parasitic infections and various aspects of cancer. They are alsoa kind of natural product and antioxidant substances capable of scavenging free superoxide
radicals, antiaging and reducing the risk of cancer. Secondary metabolites are chemicals
produced by plants; and thier functions in growth, photosynthesis, reproduction and otherprimary processes are not known yet. Most pharmaceuticals are based on plant component
structures; such as secondary metabolites enhance human immunity. Flavonoid constitute awide range of substances that play important role in protecting biological systems against
the harmful effects of oxidative processes on macromolecules, such as carbohydrate
proteins, lipids and DNA.Other flavonoid groups are aurones,xanthones and condensed
tannins. Most of flavonoid compounds, which are often accumulated in the vacuoles ofplant cells, are glycosides and always O or C linked. The variant of flavonoid glycosides arebased on number of positions on flavonoid for glycosylation and number of types of sugars
7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
New Delhi, India, 23-26 October 2013

involved in glycosylation.Among various glycogens isolated from plants only eight are
distributed widely. In addition, the most common flavonoid nuclei are kaempferol,Quercetin, rutin, catechin, epicatechin, myricetin, anthocynidines and luteolin.
SCHEME 1- CLAISEN-SCHEMIDT METHODOOH

HAcid or BaseO

I 2 /DMSO

OH+

0115 C,30 MinuteRT/HeatCH 3OOO
Reduction
Reduction

OOO
FlavoneFlavanone

FlavaneSCHEME 2 - BAKER- VENKATRAMAN METHOD

7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
New Delhi, India, 23-26 October 2013

HOOHOHHOHO

CH3COCl

OCOPh

PHCOClCH3COCH3meta cresol

AlCl 3O2,4 dihydroxy acetophenone

AcidOHOOOFlavoneO

propane1,3--dione
Reduction

Reduction

OO

O
FlavaneFlavanone

SCHEME 3 - VARIOUS METHODS FOR ANALOGUE SYNTHESIS

7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
New Delhi, India, 23-26 October 2013

R2.

R2O.

.

.
OR1OH
R1.

N

NH2
H2N

O
Flavanone

R2NO

Flavonol

R1.

NH2Pyrimidines

NH

H2O2tBuOH/tBuOK
Acids

OH

R2.
CH3
R1.

NaOH

O+OH

EtOH
CHO

O

I2/DMSO

.

Heat
R1.

O
ChalconeO

R2Flavone

PhNHNH2NH2OH.HCl

NH2OH.H2O

R1OH

R1.

NH N

R1.

.
R2.

.

NH N
H

.

3,5 diarylpyrazoline
R3

R2.

R2N

O

3,5 diarylisoxazoline

1,3,5 triarylpyrazoline
Where

R1 , R2 and R3

is OH,NO2,F,Cl,Br,I,NH
2,Me.Et,Alkyl,CHO,COOEt,COOR and aroatic or aliphatic or alicyclic or heterocyclic ring.

7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
New Delhi, India, 23-26 October 2013

SCHEME 4- FOR SYNTHESIS OF HYBRID MOLECULES

7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
New Delhi, India, 23-26 October 2013

H3C

CH3CH3

H3COO

1) Duff Reaction
OOH2) EAA/KOH/EtOH3)Benzaldehyde/Base0OH4)I2/DMSO/115CO
Flavone Coumarin HybridOH0

HMTA/TFA/120COHOO

1) EAA/KOH/EtOHOHHO

2)Benzaldehyde/BaseO

3)I2/DMSO/1150C

OOH
Different Phenols

Flavone Coumarin Hybrid
1) EAA/KOH/EtOH

1) EAA/KOH/EtOH

2)Benzaldehyde,Phenol and Base

2)Benzaldehyde/BaseO

3)I2/DMSO/1150C
OOOOOHO
Flavone Coumarin HybridO
Flavone Xanthane Hybrid

SCHEME:-5

7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
New Delhi, India, 23-26 October 2013

H 2N
RCH 3NHR

MeOH,Reflux+DMF/POCl 3 ,Reflux
CH 3O
NNH+RNOOCHO

KOH,MeOHH3CRNHONNO0I 2 /DMSO,117 CORNNEXPERIMENTAL METHODS:Aldehydes and ketone treated as per procedure to give intermediate chalcone from which
various analogues are synthesised by simple lab scale and thermal method. Processoptimisation to increase yield. Some new catalyst, molar ratio, solvent, change in physicalfactor like time, temperature etc.

7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
New Delhi, India, 23-26 October 2013

CONCLUSION: Flavonoid derivatives are synthesised by novel methods and thier biologicalactivities are tested against various bacterial and fungal stains. They show better activities
against the bacteria and viruses.
OBJECTIVES: The object of research was to design effective drug analogues against various
deseases and check thier bioactivity. Development of new methodology, which is cheap andshort route. Synthesis of some hybrid molecules and prod rugs to enhance activity ofexisting drug molecules against bacteria, viruses and fungi
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7th International Symposium on Feedstock Recycling of Polymeric Materials (7th ISFR 2013)
New Delhi, India, 23-26 October 2013