Synthesis and Characterization of Novel Heterocyclic Compounds

Containing Oxygen and Study of their Biological Activity

Plants and microorganisms elaborate a diverse range of heterocyclic compounds that are very
useful as drugs. The heterocyclics are mainly of the classes of alkaloids, flavones, chromones and
coumarins. Several synthetic compounds of these classes show different bioactivity. More than
50% of the drugs used in the modern medicine are either synthetic or natural heterocyclic
systems. A brief account of the oxygen containing heterocyclic compounds reveals that these
compounds are useful as drugs or in the various stages of a drug development due to their
biological activity.
Natural and synthetic oxygen heterocyclic compounds of the classes of flavones, chalcones,
chromenes and chromanones have several useful biological activities. Natural and synthetic
hydroxylated flavones (1-4) have gastroprotective action. They act by destroying the cancer
causing free- radicals and thereby afford protection to humans from the cancer of the
gastrointestinal tract. Flavone-8-acetic acid (mitoflaxone) (5) is an anticancer drug and is used
along with vincaleulcoblastin in the treatment of cancer. Acacetin (6) isolated from Scoparia
dulcis inhibits HSV-1 replication. Chalcones, (E)-1-(2,5-dihydroxyphenyl)-3-(3,4-
dihydroxyphenyl)-2-propen-1-one (7) and (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxy-3,4-
dimethoxyphenyl)-2-propen-1-one (8) have anti-inflammatory activity. They act by inhibition of
5-lipoxygenase and cyclooxygenase. Silibyn (9) a flavonoid isolated from Silybum marianum, is a
hepatoprotective agent, used in the treatment of jaundice.
O
OH
O OH
HO O
OH O
R2
OH
R1 O
1 R1 = R 2 = H OH O
O
2 R1 = H, R2 = OH 4
5
3 R1 = R2 = OH

OCH3

HO O

OH O
6
 OH

OH
OH

HO
O

O OH
OCH3
OCH3
HO O OCH3
3HCO OH O
OCH3
OCH3
OH O
O
8 8

Since derivatives of substituted chalcones and flavanone have some interesting biological
activities, synthesis and characterization of some novel heterocyclic compounds such as chalcones
and flavones and study of their biological activity is taken for present work.

Scheme-I

O
O

O
N
O

5-benzyl-4,5-dihydro-3-(2-phenylchroman-4-yl)isoxazole
Scheme-II

O O
O
+
CH3 CH3
CH3
O O
O

A B

A= (2R)-3-methyl-2-phenylchroman-4-one

B= (2S,3R)-3-methyl-2-phenylchroman-4-one