Literature DB >> 22850861

(1S)-1-Phenylethanaminium 4-{[(1S,2S)-1-hydroxy-2,3-dihydro-1H,1'H-[2,2'-biinden]-2-yl]methyl}benzoate.

Christopher S Frampton1, Tao Zhang, Gaia A Scalabrino, Neil Frankish, Helen Sheridan.   

Abstract

The title molecular salt, C(8)H(12)N(+)·C(26)H(21)O(3)(-), contains a dimeric indane pharmacophore that demonstrates potent anti-inflammatory activity. The indane group of the anion exhibits some disorder about the α-C atom, which appears common to many structures containing this group. A model to account for the slight disorder was attempted, but this was deemed unsuccessful because applying bond-length constraints to all the bonds about the α-C atom led to instability in the refinement. The absolute configuration was determined crystallographically as S,S,S by anomalous dispersion methods with reference to both the Flack parameter and Bayesian statistics on Bijvoet differences. The configuration was also determined by an a priori knowledge of the absolute configuration of the (1S)-1-phenylethanaminium counter-ion. The molecules pack in the crystal structure to form an infinite two-dimensional hydrogen-bond network in the (100) plane of the unit cell.

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Year:  2012        PMID: 22850861     DOI: 10.1107/S0108270112031265

Source DB:  PubMed          Journal:  Acta Crystallogr C        ISSN: 0108-2701            Impact factor:   1.172


  2 in total

Review 1.  Investigation of the Stereoselective Synthesis of the Indane Dimer PH46A, a New Potential Anti-inflammatory Agent.

Authors:  Graham R Cumming; Tao Zhang; Gaia Scalabrino; Neil Frankish; Helen Sheridan
Journal:  Org Process Res Dev       Date:  2017-11-27       Impact factor: 3.317

2.  Bioactive Indanes: Proof of Concept Study for Enantioselective Synthetic Routes to PH46A, a New Potential Anti-Inflammatory Agent.

Authors:  Tao Zhang; Gaia Scalabrino; Neil Frankish; Helen Sheridan
Journal:  Molecules       Date:  2018-06-21       Impact factor: 4.411

  2 in total

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