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Chitosan Loaded Mucoadhesive Microspheres of Gliclazide - Journal

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Best results were obtained with p-toluyl sulphonic acid for Eisomer<br />

<strong>of</strong> dothiepin (94%) while other acids also yielded more<br />

than 84%.<br />

CONCLUSION<br />

The main focus <strong>of</strong> this research work was to understand the<br />

effect <strong>of</strong> different acid catalysts on the formation <strong>of</strong> E- and Z-<br />

isomers <strong>of</strong> Dothiepin and to characterize the isomers by<br />

1 HNMR and HPLC methods. The yield <strong>of</strong> E-isomer <strong>of</strong><br />

dothiepin was achieved in the range <strong>of</strong> 89-94 %. From the<br />

experiments conducted, use <strong>of</strong> p-toluyl sulphonic acid<br />

(GKRA-13) yielded maximum <strong>of</strong> 94% E-isomer and was<br />

found to be ideal reagent for the dehydration <strong>of</strong> the alcohol<br />

[Compound-A] to form E- and Z- isomers <strong>of</strong> dothiepin.<br />

Other acids namely L(+) tartaric acid, oxalic acid and maleic<br />

acid led to the formation <strong>of</strong> E isomer in the range <strong>of</strong> 89-92%.<br />

Quantification <strong>of</strong> E- and Z-isomers <strong>of</strong> dothiepin obtained by<br />

NMR showed the range <strong>of</strong> 85:15 and 94:06 and HPLC was<br />

found to be in the range <strong>of</strong> 89:11 and 94:6.<br />

ACKNOWLEDGEMENT<br />

The authors would like to thank Pr<strong>of</strong>. B. G. Shivananda<br />

Principal, Al-Ameen College <strong>of</strong> Pharmacy, Bangalore and<br />

Mr Anjan K. Roy, Managing Director, R.L.Fine Chemicals,<br />

Bangalore for providing support and necessary facilities,<br />

Department <strong>of</strong> Inorganic and Physical Chemistry, Indian<br />

Institute <strong>of</strong> Science, Bangalore, for providing help in<br />

obtaining the various spectra.<br />

REFERENCES<br />

Gopal Krishna Rao et al./ Effect <strong>of</strong> Different Acids on the Formation <strong>of</strong> E and Z Isomers <strong>of</strong> Dothiepin<br />

1. Greven J, Defrain W, Glaser K, Meywald K, Heidenreich O. Studies<br />

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Pharmacol let 2000;66(23):325-30.<br />

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Res.2010;Oct-Dec.44(3):345-9.<br />

6. Martin T, Ulrike H. Utilizing NMR spectroscopy for assessing drug<br />

enantiomeric composition. Magnetic resonance in chemistry 1998;<br />

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7. Lane RM,Baker GB. Chirality and drugs used in psychiatry: Nice to<br />

know or need to know? Cellular and molecular neurobiology 1999;<br />

19(3):355-67.<br />

8. Pieter W, Stefan W, Leslie AT, Kendall C. HPLC determinations <strong>of</strong><br />

enantiomeric ratios.Chirality 2007;19: 5-9.<br />

9. Richard MG,Brian C. Practical strategy for the analytical separation <strong>of</strong><br />

enantiomers by HPLC. J Chromat 1991;553:357-63.<br />

10. Lednicer D, Mitscher LA, The organic chemistry <strong>of</strong> drug synthesis-Vol-<br />

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Address for Correspondence<br />

Gopal Krishna Rao, Department <strong>of</strong> Pharmaceutical Chemistry, Al-Ameen<br />

College <strong>of</strong> Pharmacy, Bangalore, Karnataka, India<br />

E-mail: gkfadnis@gmail.com<br />

RJPS, Jul - Sep, 2011/ Vol 1/ Issue 2

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