New thiazolidinyl analogs containing pyridine ring: synthesis, biological evaluation and QSAR studies

作者：Ranga Reetu; Sharma Vikas; Kumar Vipin^*

来源：Medicinal Chemistry Research, 2013, 22(4): 1538-1548.

DOI：10.1007/s00044-012-0149-0

• Analgesic activity
• Anti-inflammatory
• COX-2 inhibitors
• Docking
• QSAR

A series of pyridine derivatives of thiazolidin-4-ones (4a-4o) has been synthesized. Structures of these compounds were established on the basis of elemental analysis, IR, H-1 NMR, C-13 NMR, and Mass spectral data. All the synthesized compounds have been evaluated for their anti-inflammatory and analgesic effects. The results showed that compound 2-[4-methylphenylimino]-5-(1H-pyridin-2-ylmethylidene)-1,3-thiazolidin-4-one (4d), 2-(2,4-dinitro-phenylhydrazinylidine)-5-(1H-pyridin-2-yl-methylidene)-1,3-thiazolidin-4-one (4h), and 2-[3-nitro-phenylimino]-5-(1H-pyridin-2-yl-methylidene)-1,3-thiazolidin-4-one (4j) exhibited good anti-inflammatory and analgesic activity. Compound 4h was found to be the most active compound of the series with an interesting dual anti-inflammatory and analgesic activity. Docking simulation was performed to position synthesized compounds into the active site of COX-2. The relationships of energy-based docking score with analgesic and anti-inflammatory activities were also investigated by linear regression method. The QSAR models with R (2) of 0.621 and 0.740 were developed for analgesic and anti-inflammatory activities, respectively.

• 出版日期2013-4