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Synthesis of Some New Bischromones from Bischalcones

Volume 29, Number 2

K. G. Huge1*, V. M. Gurav2 and S. V. Anurkar1

1Department of Chemistry, K.K.M. College, Manwath, Dist. Parbhani, Maharashtra, India. 2Department of Chemistry, Yeshwant Mahavidayala, Nanded, Maharashtra, India.

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Article Published : 10 Jun 2013
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ABSTRACT:

Some novel Di (6/8-chloro-8/6-Chromonyl) Methyl ethers i.e. Bischromones –I & II were synthesized by oxidative cyclisation of Di (5’-chloro-4’/2’-hydroxy-3’-chalconyl) methyl ethers i.e. Bischalcones- I & II and screened for antifungal activity.

KEYWORDS:

Synthesis; Bischromones and Bischalcones

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Huge K. G, Gurav V. M, Anurkar S. V. Synthesis of Some New Bischromones from Bischalcones. Orient J Chem 2013;29(2).

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Introduction

The Bischromones are used primarily in treating allergic asthma, exercise-induced asthma, sometimes in intrinsic asthma and also in the studies of various allergic lung diseases1. Chromolyn sodium (Intal) is used principally in the treatment of bronchial asthma2. It is the only biscromone drug now licensed by the Food & Drug Administration3. It is available as a powder and in capsule form. The Disodiumchromoglycate (DSCG/INTAL) and related compounds there of, including generally bischromones as anti allergenic, anti-PACVIS (Pathological cardiovascular ischemic state) agents4, and in the treatment of Bronchial asthma in children5. It also have an effect on the release of bistamine & degranulation of rat mast cells6. The Disodiumchromoglycate (DSCG) related compounds shows inhibition of homologous passive cutaneous anaphylaxis (PCA)7. Lomudal inhibits the bronchospam induced by the antigen & inhibits least partially the post exercise fall in FEV in children and adults8. A khelin like 7,7’-Glycerol bridged bischromone found anti anaphylacetic antivit9.

Use of bischromones in studies of various allergic lung diseases has provided researchers with valuable information about the body’s immune mechanisms. Therefore it was thought worthwhile to synthesize some new bischromones from bischalcones.

General Method

A mixture of Bischalcones-I/II (0.01 mole) and selenium oxide (0.08 mole) in isoamyl alcohol (50 ml) was refluxed for 10-12 hours. The reaction mixture was cooled and filtered to remove black precipitate of selenium formed during the reaction. Isoamyl alcohol from the filterate was removed by steam distillation and non-volatile residue thus obtained was extracted with hot benzene. Benzene layer was washed with aqueous NaHCO3 (10%) and then by distilled water to remove any acidic and water soluble impurities. The benzene was removed by evaporation and residue was crystallized from proper solvent (Scheme-I).

Scheme 1: Scheme 1:


Click here to View schem

Experimental

The purity of the compounds was checked by TLC. Melting points of the compounds were determined in open capillary tubes and are incorrected. The IR spectra were recorded on Perkin-Elmer IR Infra cord in KBr disc.  1H-NMR spectra were recorded on a 300 MHz Brucker spectrometer using TMS as an internal standard.  The titled compounds Bischromons-I & II i.e. Di (6/8- chloro-2-phenyl-8/6-Chromonyl) methyl ethers were synthesized by oxidative cyclisation of Bischalcones I & II i.e. Di (5’-chloro-4’/2’-hydroxy-3’-chalconyl) methyl ethers. These Bischalcones I & II on refluxing with SeO2 in isoamyl alcohol for 10 hrs., afforded Bis- Chromones- I & II (Table-I & II)

[Table-I] : Di (8-chloro-6-Chromonyl) Methyl ethers i.e. Bischromones-I
Sr. R. M.P.(oC) Yield (%) Analysis found (Calcd) Chlorine
Phenyl 251 50 12.67 (12.79)
o-Chlorophenyl 162 65 22.42 (12.79)
p-Chlorophenyl 242 65 22.58 (22.75)
o-Methyl phenyl 233 70 12.48 (12.17)
p-Methoxy phenyl 225 72 11.33 (12.09)
o-Hydroxy phenyl 213 50 12.48 (12.09)
m-Hydroxy phenyl 217 68 12.47 (12.09)
p-Hydroxy phenyl 238 75 12.47 (12.09)
a-Naphthyl 266 70 10.62 (10.83)
[Table-II] : Di (6-chloro-8-Chromonyl) Methyl ethers i.e. Bischromones-II
Sr. R. M.P.(oC) Yield (%) Analysis found (Calcd) Chlorine
Phenyl 226 50 12.67 (12.79)
o-Chlorophenyl 161 62 22.52 (22.75)
p-Chlorophenyl 216 60 22.38 (22.75)
o-Methyl phenyl 210 60 12.67 (12.17)
p-Methoxy phenyl 246 70 11.32 (12.09)
a-Naphthyl 261 75 10.62 (10.83)

Discussion of IR and 1H-NMR

The representative member [comp.-1(Bischromons-I, from Table-I)] have shown following spectral data.

IR (KBr)

nmax cm-1:1635 (C=O), 1364-1361 (Pyrone-oxide vibration), 1563-1538 (ethylenic bond), 1100-1080 (asymmetrical (C-O-C stretch)

1H-NMR

(CDCl3, 300 MHz), dppm : 8.22 [d,2H,Jm=2.6 Hz,(H-5)], 8.07 [m,4H (H-2’,6’)], 7.60 [d,2H,Jm=2.6Hz,(H-7)],7.50 [m,6H, (H-3’,4’,5’], 6.78 [s,2H,(H-3)] ,4.03 [s,4H, (2HC-O-CH2)]

Therefore the structure of comp.-1 is  Hence, the name of the compound is Di (8-chloro-2-phenyl-6-Chromonyl) Methyl ether.

Vol_29-no2_Synt_Huge-comp1

Antifungal Activity

The antifungal screening of some of the representative compounds of  the type I and II was carried out by dry weight method. In general they were found to be stimulatory against Penicillium Notatum at 100 ppm and 250 ppm concentrations.

Acknowledgement

The authors would like to thank Dr. N.V. Kalyankar, Principal, Yeshwant Mahavidyalaya, Nanded  for providing laboratory facilities.

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