Literature DB >> 19740655

Diastereoisomers of 2-benzyl-2, 3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol: potential anti-inflammatory agents.

Helen Sheridan1, John J Walsh, Carina Cogan, Michael Jordan, Tom McCabe, Egle Passante, Neil H Frankish.   

Abstract

The synthesis and biological activity of the novel diastereoisomers of 2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol is reported. The 2,2-coupled indane dimers were synthesised by coupling of the silyl enol ether of 1-indanone with the dimethyl ketal of 2-indanone. The coupled product was directly alkylated to give the racemic ketone which was reduced to the diastereoisomeric alcohols. The alcohols were separated and their relative stereochemistry was established by X-ray crystallography. These molecules demonstrate significant anti-inflammatory activity in vivo and in vitro and may represent a new class of anti-inflammatory agent.

Entities:  

Mesh:

Substances:

Year:  2009        PMID: 19740655     DOI: 10.1016/j.bmcl.2009.08.060

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  7 in total

Review 1.  Twenty-first century mast cell stabilizers.

Authors:  D F Finn; J J Walsh
Journal:  Br J Pharmacol       Date:  2013-09       Impact factor: 8.739

2.  Molecular structure studies of (1S,2S)-2-benzyl-2,3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol.

Authors:  Tao Zhang; Krzysztof Paluch; Gaia Scalabrino; Neil Frankish; Anne-Marie Healy; Helen Sheridan
Journal:  J Mol Struct       Date:  2015-03-05       Impact factor: 3.196

3.  Bioactive indanes: insight into the bioactivity of indane dimers related to the lead anti-inflammatory molecule PH46A.

Authors:  Kit Chan; Neil Frankish; Tao Zhang; Abdulilah Ece; Aoife Cannon; Jacintha O'Sullivan; Helen Sheridan
Journal:  J Pharm Pharmacol       Date:  2020-04-16       Impact factor: 3.765

4.  Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus Botrytis cinerea.

Authors:  Cristina Pinedo-Rivilla; Javier Moraga; Guillermo Pérez-Sasián; Alba Peña-Hernández; Isidro G Collado; Josefina Aleu
Journal:  Plants (Basel)       Date:  2020-11-25

5.  2-(Di-phenyl-methyl-idene)-2,3-di-hydro-1H-inden-1-one.

Authors:  Tao Zhang; Vilmar Bandero; Tom McCabe; Neil Frankish; Helen Sheridan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-07-24

6.  The indane diastereoisomers, PH2 and PH5: divergence between their effects in delayed-type hypersensitivity models and a model of colitis.

Authors:  Neil H Frankish; Brendan McHale; Helen Sheridan
Journal:  J Pharm Pharmacol       Date:  2017-10-23       Impact factor: 3.765

7.  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

  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.