Literature DB >> 11695625

Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling.

H J Lehmler1, L W Robertson.   

Abstract

An improved synthesis of hydroxylated polychlorinated biphenyls (PCBs) which are structurally related to the major hydroxy PCB congeners identified in human plasma is described. The coupling of (chlorinated) aryl boronic acids with bromochloro anisoles using the standard conditions of the Suzuki coupling gave the desired hydroxylated PCB metabolites in good to excellent yields. The approach offers the advantage of high selectivity and good yields compared to conventional methods such as the Cadogan reaction and allows the use of less toxic starting materials.

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Year:  2001        PMID: 11695625     DOI: 10.1016/s0045-6535(01)00052-2

Source DB:  PubMed          Journal:  Chemosphere        ISSN: 0045-6535            Impact factor:   7.086


  37 in total

1.  Synthesis of Sterically Hindered Polychlorinated Biphenyl Derivatives.

Authors:  S N Joshi; S M Vyas; M W Duffel; S Parkin; H-J Lehmler
Journal:  Synthesis (Stuttg)       Date:  2011-01-01       Impact factor: 3.157

2.  Improved syntheses of non-dioxin-like polychlorinated biphenyls (PCBs) and some of their sulfur-containing metabolites.

Authors:  Sanjay Telu; Sean Parkin; Larry W Robertson; Hans-Joachim Lehmler
Journal:  Environ Int       Date:  2009-03-03       Impact factor: 9.621

3.  Hydroxylated and sulfated metabolites of commonly occurring airborne polychlorinated biphenyls inhibit human steroid sulfotransferases SULT1E1 and SULT2A1.

Authors:  Victoria S Parker; Edwin J Squirewell; Hans-Joachim Lehmler; Larry W Robertson; Michael W Duffel
Journal:  Environ Toxicol Pharmacol       Date:  2018-02-03       Impact factor: 4.860

4.  Structure-activity relationships for hydroxylated polychlorinated biphenyls as inhibitors of the sulfation of dehydroepiandrosterone catalyzed by human hydroxysteroid sulfotransferase SULT2A1.

Authors:  Edugie J Ekuase; Yungang Liu; Hans-Joachim Lehmler; Larry W Robertson; Michael W Duffel
Journal:  Chem Res Toxicol       Date:  2011-09-28       Impact factor: 3.739

5.  Detection of 3,3'-Dichlorobiphenyl in Human Maternal Plasma and Its Effects on Axonal and Dendritic Growth in Primary Rat Neurons.

Authors:  Sunjay Sethi; Kimberly P Keil; Hao Chen; Keri Hayakawa; Xueshu Li; Yanping Lin; Hans-Joachim Lehmler; Birgit Puschner; Pamela J Lein
Journal:  Toxicol Sci       Date:  2017-08-01       Impact factor: 4.849

6.  Inhibition of cytochromes P450 and the hydroxylation of 4-monochlorobiphenyl in whole poplar.

Authors:  Guangshu Zhai; Hans-Joachim Lehmler; Jerald L Schnoor
Journal:  Environ Sci Technol       Date:  2013-01-24       Impact factor: 9.028

7.  Transformation of hydroxylated derivatives of 2,5-dichlorobiphenyl and 2,4,6-trichlorobiphenyl by Burkholderia xenovorans LB400.

Authors:  Rouzbeh Tehrani; Monica M Lyv; Benoit Van Aken
Journal:  Environ Sci Pollut Res Int       Date:  2013-04-16       Impact factor: 4.223

8.  Induction of cytochrome P450 1A1 in MCF-7 human breast cancer cells by 4-chlorobiphenyl (PCB3) and the effects of its hydroxylated metabolites on cellular apoptosis.

Authors:  Anna Ptak; Gabriele Ludewig; Agnieszka Rak; Weronika Nadolna; Michał Bochenek; Ewa L Gregoraszczuk
Journal:  Environ Int       Date:  2009-07-14       Impact factor: 9.621

9.  In vivo biotransformation of 3,3',4,4'-tetrachlorobiphenyl by whole plants-poplars and switchgrass.

Authors:  Jiyan Liu; Dingfei Hu; Guibin Jiang; Jerald L Schnoor
Journal:  Environ Sci Technol       Date:  2009-10-01       Impact factor: 9.028

10.  Electron ionization mass spectral fragmentation study of sulfation derivatives of polychlorinated biphenyls.

Authors:  Xueshu Li; Larry W Robertson; Hans-Joachim Lehmler
Journal:  Chem Cent J       Date:  2009-03-09       Impact factor: 4.215

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