Synthesis, Characterization and Evaluation of Anti-inflammatory and Analgesic Activity of Some Novel Quinoline Based Thiazolidinone Heterocycles | ||
| Egyptian Journal of Chemistry | ||
| Article 35, Volume 61, Conference issue (14th Ibn Sina Arab Conference on Heterocyclic Chemistry and its Applications (ISACHC 2018), 30 March-2 April 2018, Hurgada, Egypt)., November and December 2018, Pages 67-77 PDF (688.1 K) | ||
| Document Type: Original Article | ||
| DOI: 10.21608/ejchem.2018.5155.1456 | ||
| Authors | ||
| Atef Amer* 1; Ali Deeb1; Wafaa I. El-Eraky2; Sally A. El Awdan2; Sebaey Mahgoub3 | ||
| 1Department of Chemistry, Faculty of Science, Zagazig University, Egypt | ||
| 2Department of Pharmacology, National Research Centre, Cairo, Egypt | ||
| 3Research and Development, Unipharma, El-Obour City, Egypt. | ||
| Abstract | ||
| In this paper we report the synthesis of some quinoline based thiazolidinone derivatives (13–22) in a three-step process. Condensation of 2-hydrazinylquinoline 2 with different aromatic aldehydes gave the corresponding Schiff bases 3-10 which in turn were reacted with thioglycolic acid to furnish the corresponding thiazolidinone derivatives 13-20. Reaction of compound 2 with isatin or methyl isatin gave 1-sustituted-3-(2-(quinolin-2-yl)hydrazono)indolin-2-ones 11 and 12, which were converted to 1-substituted 3'-(quinolin-2-ylamino)spiro[indoline-3,2'-thiazolidine]-2,4'-dione 21 and 22 by cyclocondensation with thioglycolic acid. All newly synthesized compounds have been characterized by means of elemental analyses, IR, 1H NMR and MS. Furthermore, all new thiazolidinone derivatives were evaluated for their anti-inflammatory and analgesic activity. The Study results revealed that the highest anti-inflammatory potency was gained by 6 derivatives according to the following order 22 > 17 >13 > 14 > 21 > 15, showing a good edema inhibition compared to the reference drug indomethacin. Compound 22 carrying indole ring system inhibited the edema volume significantly at the 1st h post administration, and the activity was enhanced up to the 4th h giving a promising edema volume inhibition compared to that produced by indomethacin. The longest duration of analgesic action up to 90 min post compounds administration was obtained by the compounds 13, 17 and 22, they exhibited a potent analgesia compared to that obtained by aspirin. | ||
| Keywords | ||
| Quinoline; thiazolidinone; spiro[indoline-3; 2'-thiazolidine]-2; 4'-dione; Synthesis; anti-inflammatory and analgesic activity | ||
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