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

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URI: http://hdl.handle.net/10498/20451

DOI: 10.1021/cg401842y

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2014-Polymorphic signature of the anti-inflammatory activity of 2,2′-[1,2-Phenylenebis(methylene)]bis(sulfanediyl)bis(4, 6-dimethylnicotinonitrile).pdf (1.990Mb)
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Dubey, Rashmi; Singh, Praveen; K. Singh, Ajeet; K. Yadav, Manoj; Swati, D.; Vinayak, Manjula; Ravi Kumar, K.; Sridhar, B.; K. Tewari, Ashish; Puerta Vizcaino, María del Carmen; Valerga Jiménez, Pedro Sixto
Date
2014-02
Department
Ciencia de los Materiales e Ingeniería Metalúrgica y Química Inorgánica
Source
Crystal Growth & Design 2014, 14, 1347−1356
Abstract
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′- {[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 4a and 4b, respectively, while in acetic acid, it gave metastable polymorph 4c. The polymorphic behavior of the compound has been visualized through singlecrystal X-ray and Hirshfeld analysis. These polymorphs are tested for anti-inflammatory activity via the complete Freund’s 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.
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Attribution-NonCommercial-NoDerivatives 4.0 Internacional
This work is under a Creative Commons License Attribution-NonCommercial-NoDerivatives 4.0 Internacional

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