Polymorphic Signature of the Anti-inflammatory Activity of 2,2鈥?{[1,2-Phenylenebis(methylene)]bis(sulfanediyl)}bis(4,6-dimethylnicotinonitrile)

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• 作者：Rashmi Dubey ; Praveen Singh ; Ajeet K. Singh ; Manoj K. Yadav ; D. Swati ; Manjula Vinayak ; Carmen Puerta ; Pedro Valerga ; K. Ravi Kumar ; B. Sridhar ; Ashish K. Tewari
• 刊名：Crystal Growth & Design
• 出版年：2014
• 出版时间：March 5, 2014
• 年：2014
• 卷：14
• 期：3
• 页码：1347-1356
• 全文大小：725K
• 年卷期：v.14,no.3(March 5, 2014)
• ISSN：1528-7505

文摘

Weak noncovalent interactions are the basic forces in crystal engineering. Polymorphism in flexible molecules is very common, leading to the development of the crystals of same organic compounds with different medicinal and material properties. Crystallization of 2,2鈥?{[1,2-phenylenebis(methylene)]bis(sulfanediyl)}bis(4,6-dimethylnicotinonitrile) by evaporation at room temperature from ethyl acetate and hexane and from methanol and ethyl acetate gave stable polymorphs <b>4ab> and <b>4bb>, respectively, while in acetic acid, it gave metastable polymorph <b>4cb>. The polymorphic behavior of the compound has been visualized through single-crystal X-ray and Hirshfeld analysis. These polymorphs are tested for anti-inflammatory activity via the complete Freund鈥檚 adjuvant-induced rat paw model, and compounds have exhibited moderate activities. Studies of docking in the catalytic site of cyclooxygenase-2 were used to identify potential anti-inflammatory lead compounds. These results suggest that the supramolecular aggregate structure, which is formed in solution, influences the solid state structure and the biological activity obtained upon crystallization.