Anti-inflammatory activities of some newly synthesized substituted thienochromene and Schiff base derivatives

Anti-inflammatory activities of some newly synthesized substituted thienochromene and Schiff base... A series of newly substituted thieno[3,2-g]chromene derivatives were synthesized from 1-(7-mercapto-2,2-dimethylchroman-6-yl)ethanone (3) as starting material. The compound 3 in turn was synthesized by reacting of 1-(2,4-dihydroxyphenyl)ethanone with isoprene to get compound 2 followed by its reaction with phosphorus pentasulfide. Condensation of 3 with N-phenylchloroacetamide or phenacylbromide gave the corresponding thienochromene derivatives 5 and 6. Also, compound 3 was reacted with maleic anhydride and acrylonitrile to afford the corresponding derivatives 8 and 9, respectively. Alkylation of 3 with diazomethane or ethyl bromoacetate afforded the corresponding S-substituted derivatives 10 and 11. The latter compound 11 was cyclized to ester derivative 12, which was obtained directly from 3 on reaction with ethyl bromoacetate. Treatment of 12 with hydrazine hydrate afforded the corresponding hydrazide 13, which was condensed with aromatic aldehydes or acetyl acetone to yield the corresponding Schiff’s bases 14a–d S-pyrazolo derivative 15, respectively. Finally, compound 13 was treated with 2,5-hexandione or carbon disulfide to give the corresponding compounds 16 and 17, respectively. Some of the newly synthesized compounds exhibited better anti-inflammatory activities than the reference controls with low concentrations. The structures of newly synthesized compounds were confirmed by chemical, elemental, and spectroscopic evidences. The detailed synthesis, spectroscopic data, and pharmacological activities were reported. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Anti-inflammatory activities of some newly synthesized substituted thienochromene and Schiff base derivatives

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Publisher
Springer Netherlands
Copyright
Copyright © 2013 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-013-1366-y
Publisher site
See Article on Publisher Site

Abstract

A series of newly substituted thieno[3,2-g]chromene derivatives were synthesized from 1-(7-mercapto-2,2-dimethylchroman-6-yl)ethanone (3) as starting material. The compound 3 in turn was synthesized by reacting of 1-(2,4-dihydroxyphenyl)ethanone with isoprene to get compound 2 followed by its reaction with phosphorus pentasulfide. Condensation of 3 with N-phenylchloroacetamide or phenacylbromide gave the corresponding thienochromene derivatives 5 and 6. Also, compound 3 was reacted with maleic anhydride and acrylonitrile to afford the corresponding derivatives 8 and 9, respectively. Alkylation of 3 with diazomethane or ethyl bromoacetate afforded the corresponding S-substituted derivatives 10 and 11. The latter compound 11 was cyclized to ester derivative 12, which was obtained directly from 3 on reaction with ethyl bromoacetate. Treatment of 12 with hydrazine hydrate afforded the corresponding hydrazide 13, which was condensed with aromatic aldehydes or acetyl acetone to yield the corresponding Schiff’s bases 14a–d S-pyrazolo derivative 15, respectively. Finally, compound 13 was treated with 2,5-hexandione or carbon disulfide to give the corresponding compounds 16 and 17, respectively. Some of the newly synthesized compounds exhibited better anti-inflammatory activities than the reference controls with low concentrations. The structures of newly synthesized compounds were confirmed by chemical, elemental, and spectroscopic evidences. The detailed synthesis, spectroscopic data, and pharmacological activities were reported.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Aug 22, 2013

References

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