title: Selective biocatalytic aminolysis of (±)-epichlorohydrin: synthesis and ICAM-1 inhibitory activity of (S)-(+)-3-arylamino-1-chloropropan-2-ols.
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.
authors.affiliation: Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India.
authors.forename: Pankaj
authors.initials: P
authors.lastname: Gupta
authors.forename: Sumati
authors.initials: S
authors.lastname: Bhatia
authors.forename: Ashish
authors.initials: A
authors.lastname: Dhawan
authors.forename: Sakshi
authors.initials: S
authors.lastname: Balwani
authors.forename: Shatrughan
authors.initials: S
authors.lastname: Sharma
authors.forename: Raju
authors.initials: R
authors.lastname: Brahma
authors.forename: Rajpal
authors.initials: R
authors.lastname: Singh
authors.forename: Balaram
authors.initials: B
authors.lastname: Ghosh
authors.forename: Virinder S
authors.initials: VS
authors.lastname: Parmar
authors.forename: Ashok K
authors.initials: AK
authors.lastname: Prasad
mesh_terms: D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D055162:Biocatalysis; D002448:Cell Adhesion / Q000187:drug effects; D042783:Endothelial Cells / Q000166:cytology / Q000187:drug effects; D004811:Epichlorohydrin / Q000737:chemistry*; D006801:Humans; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018799:Intercellular Adhesion Molecule-1 / Q000096:biosynthesis*; D008049:Lipase / Q000737:chemistry / Q000378:metabolism; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D000893:Anti-Inflammatory Agents; D006843:Hydrocarbons, Chlorinated; D020005:Propanols; D014409:Tumor Necrosis Factor-alpha; D004811:Epichlorohydrin; D018799:Intercellular Adhesion Molecule-1; D008049:Lipase