Gupta, Pankaj ; Bhatia, Sumati ; Dhawan, Ashish ; Balwani, Sakshi ; Sharma, Shatrughan ; Brahma, Raju ; Singh, Rajpal ; Ghosh, Balaram ; Parmar, Virinder S. ; Prasad, Ashok K. (2011) Selective biocatalytic aminolysis of (±)-epichlorohydrin: synthesis and ICAM-1 inhibitory activity of (S)-(+)-3-arylamino-1-chloropropan-2-ols Bioorganic and Medicinal Chemistry, 19 (7). pp. 2263-2268. ISSN 0968-0896
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.bmc.2011.02.029
Abstract
Regio- and enantioselective synthesis of (S)-(+)-3-arylamino-1-chloropropan-2-ols has been achieved by the epoxide ring opening of (±)-epichlorohydrin with different aromatic amines in the presence of Candida rugosa lipase. Activities of seven model (S)-(+)-3-arylamino-1-chloropropan-2-ols, out of 10 compounds synthesized, have been evaluated for the inhibition of tumor necrosis factor-α TNF-α) induced expression of intercellular adhesion molecule-1 (ICAM-1), which is one of the factors responsible for the modulation of inflammation in biological systems; (S)-(+)-1-chloro-3-(2'-chlorophenylamino)-propan-2-ol has been found to exhibit highest activity, that is, 86% inhibition of TNF-α induced expression of ICAM-1 at a concentration of 40 μg/ml.
Item Type: | Article |
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Source: | Copyright of this article belongs to Elsevier Science. |
Keywords: | β-amino Alcohol; (S)-(+)-3-arylamino-1-chloropropan-2-ols; Candida rugosa Lipase; Regioselective; Enantioselective; TNF-α; ICAM-1; Anti-inflammatory |
ID Code: | 66071 |
Deposited On: | 21 Oct 2011 03:45 |
Last Modified: | 21 Oct 2011 03:45 |
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