Literature DB >> 15638250

Review of chemical syntheses of 7-keto-delta5-sterols.

Edward J Parish1, Stephen A Kizito, Zhihai Qiu.   

Abstract

Steroids bearing ketone functionality at carbon-7 are found commonly in nature, and the most prevalent of these are the 7-keto-delta5-sterols. These substances have diverse biological properties and are present in biological samples and food products. For the purpose of studying this class of oxysterols, many chemical methods, involving the chemical oxidation of delta5-sterols to the corresponding 7-keto-delta5-sterol derivatives have been developed to produce these compounds. We have undertaken a review and evaluation of chemical methods for the synthesis of these compounds and have endeavored to enhance one of these procedures to yield products for chemical and biological investigations.

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Year:  2004        PMID: 15638250     DOI: 10.1007/s11745-004-1299-y

Source DB:  PubMed          Journal:  Lipids        ISSN: 0024-4201            Impact factor:   1.646


  12 in total

1.  Selective oxidation of steroidal allylic alcohols using pyrazole and pyridinium chlorochoromate.

Authors:  E J Parish; S Chitrakorn; S Lowery
Journal:  Lipids       Date:  1984-07       Impact factor: 1.880

2.  Studies of the oxysterol inhibition of tumor cell growth.

Authors:  E J Parish; S Chitrakorn; B Luu; G Schmidt; G Ourisson
Journal:  Steroids       Date:  1989 Mar-May       Impact factor: 2.668

3.  A facile synthesis and carbon-13 nuclear magnetic resonance spectral properties of 7-ketocholesteryl benzoate.

Authors:  E J Parish; T Y Wei; P Livant
Journal:  Lipids       Date:  1987-10       Impact factor: 1.880

Review 4.  Sterol biosynthesis.

Authors:  G J Schroepfer
Journal:  Annu Rev Biochem       Date:  1981       Impact factor: 23.643

5.  The synthesis of spermine analogs of the shark aminosterol squalamine.

Authors:  Youheng Shu; Stephen R Jones; William A Kinney; Barry S Selinsky
Journal:  Steroids       Date:  2002-03       Impact factor: 2.668

6.  Optimization of the allylic oxidation in the synthesis of 7-keto-delta5-steroidal substrates.

Authors:  Evaggelia S Arsenou; Anna I Koutsourea; Manolis A Fousteris; Sotiris S Nikolaropoulos
Journal:  Steroids       Date:  2003-05       Impact factor: 2.668

7.  Comparative effects of 7 beta-hydroxycholesterol towards murine lymphomas, lymphoblasts and lymphocytes: selective cytotoxicity and blastogenesis inhibition.

Authors:  H Hietter; P Bischoff; J P Beck; G Ourisson; B Luu
Journal:  Cancer Biochem Biophys       Date:  1986-12

8.  Biological activity of some oxygenated sterols.

Authors:  A A Kandutsch; H W Chen; H J Heiniger
Journal:  Science       Date:  1978-08-11       Impact factor: 47.728

Review 9.  Biological effects of oxysterols: current status.

Authors:  F Guardiola; R Codony; P B Addis; M Rafecas; J Boatella
Journal:  Food Chem Toxicol       Date:  1996-02       Impact factor: 6.023

10.  Correlation between oxysterol binding to a cytosolic binding protein and potency in the repression of hydroxymethylglutaryl coenzyme A reductase.

Authors:  F R Taylor; S E Saucier; E P Shown; E J Parish; A A Kandutsch
Journal:  J Biol Chem       Date:  1984-10-25       Impact factor: 5.157

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  2 in total

1.  Optimal TBHP allylic oxidation of Delta5-steroids catalyzed by dirhodium caprolactamate.

Authors:  Hojae Choi; Michael P Doyle
Journal:  Org Lett       Date:  2007-11-21       Impact factor: 6.005

Review 2.  Bismuth(III) reagents in steroid and terpene chemistry.

Authors:  Jorge A R Salvador; Samuel M Silvestre; Rui M A Pinto
Journal:  Molecules       Date:  2011-04-04       Impact factor: 4.411

  2 in total

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