Literature DB >> 12816425

Synthesis of alpha-fluorinated phosphonates from alpha-fluorovinylphosphonates: a new route to analogues of lysophosphatidic acid.

Yong Xu1, Lian Qian, Glenn D Prestwich.   

Abstract

A versatile, efficient method for the preparation of alpha-monofluoromethylene (-CHF-) phosphonates from alpha-fluorovinylphosphonate provides access to a class of lysophosphatidic acid (LPA) receptor-subtype agonists. In addition, sn-2 O-methylation of alpha-monofluoromethylene phosphonates using trimethylsilyldiazomethane generated sn-1-acyl, 2-O-methyl alpha-monofluoromethylene derivatives. Finally, a novel method for the selective etherification of 1,2-diols was developed and a new class of sn-1 O-methyl, 2-acyl alpha-monofluoromethylene LPA analogues was prepared. [reaction: see text]

Entities:  

Mesh：

Substances：

Year:  2003        PMID： 12816425     DOI： 10.1021/ol034597+

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists.

Authors:  Frank W Foss; Ashley H Snyder; Michael D Davis; Michael Rouse; Mark D Okusa; Kevin R Lynch; Timothy L Macdonald
Journal:  Bioorg Med Chem       Date:  2006-11-01       Impact factor: 3.641

2.  Chemical synthesis and molecular recognition of phosphatase-resistant analogues of phosphatidylinositol-3-phosphate.

Authors:  Yong Xu; Stephanie A Lee; Tatiana G Kutateladze; Diego Sbrissa; Assia Shisheva; Glenn D Prestwich
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

3.  Aromatic phosphonates inhibit the lysophospholipase D activity of autotaxin.

Authors:  Guowei Jiang; Damian Madan; Glenn D Prestwich
Journal:  Bioorg Med Chem Lett       Date:  2011-03-23       Impact factor: 2.823

4.  1-(Fluoroalkylidene)-1,1-bisphosphonic acids are potent and selective inhibitors of the enzymatic activity of Toxoplasma gondii farnesyl pyrophosphate synthase.

Authors:  Sergio H Szajnman; Valeria S Rosso; Leena Malayil; Alyssa Smith; Silvia N J Moreno; Roberto Docampo; Juan B Rodriguez
Journal:  Org Biomol Chem       Date:  2012-01-03       Impact factor: 3.876

5.  P1,P2-diimidazolyl derivatives of pyrophosphate and bis-phosphonates--synthesis, properties, and use in preparation of dinucleoside tetraphosphates and analogs.

Authors:  Ivan B Yanachkov; Edward J Dix; Milka I Yanachkova; George E Wright
Journal:  Org Biomol Chem       Date:  2010-11-17       Impact factor: 3.876

Review 6.  Phosphatase-resistant analogues of lysophosphatidic acid: agonists promote healing, antagonists and autotaxin inhibitors treat cancer.

Authors:  Glenn D Prestwich; Joanna Gajewiak; Honglu Zhang; Xiaoyu Xu; Guanghui Yang; Monica Serban
Journal:  Biochim Biophys Acta       Date:  2008-04-08

7.  Alpha-substituted phosphonate analogues of lysophosphatidic acid (LPA) selectively inhibit production and action of LPA.

Authors:  Guowei Jiang; Yong Xu; Yuko Fujiwara; Tamotsu Tsukahara; Ryoko Tsukahara; Joanna Gajewiak; Gabor Tigyi; Glenn D Prestwich
Journal:  ChemMedChem       Date:  2007-05       Impact factor: 3.466

8.  alpha- and beta-substituted phosphonate analogs of LPA as autotaxin inhibitors.

Authors:  Peng Cui; William F McCalmont; Jose L Tomsig; Kevin R Lynch; Timothy L Macdonald
Journal:  Bioorg Med Chem       Date:  2007-12-04       Impact factor: 3.641

9.  Antiparasitic Activity of Sulfur- and Fluorine-Containing Bisphosphonates against Trypanosomatids and Apicomplexan Parasites.

Authors:  Tamila Galaka; Mariana Ferrer Casal; Melissa Storey; Catherine Li; María N Chao; Sergio H Szajnman; Roberto Docampo; Silvia N J Moreno; Juan B Rodriguez
Journal:  Molecules       Date:  2017-01-04       Impact factor: 4.411

10.  Lysophosphatidic acid induces neointima formation through PPARgamma activation.

Authors:  Chunxiang Zhang; Daniel L Baker; Satoshi Yasuda; Natalia Makarova; Louisa Balazs; Leonard R Johnson; Gopal K Marathe; Thomas M McIntyre; Yong Xu; Glenn D Prestwich; Hoe-Sup Byun; Robert Bittman; Gabor Tigyi
Journal:  J Exp Med       Date:  2004-03-08       Impact factor: 14.307
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.