Literature DB >> 25364061

Convenient synthesis of N1-substituted orotic acid derivatives.

Jeannette T Bowler1, Caitlin R Clausen1, Daniel J Blackburn1, Weiming Wu1.   

Abstract

A convenient and efficient method for the synthesis of N1-substituted orotic acid derivatives is reported. The synthetic route utilizes substituted maleimide as synthetic intermediate and takes only four simple steps from readily available starting materials. As a result, orotic acid derivatives with various alkyl and aromatic groups at N1 can be readily synthesized.

Entities:  

Keywords:  Orotic acid; bromomaleimide; dibromosuccinimide; maleimide; orotidine; synthesis

Year:  2014        PMID： 25364061      PMCID： PMC4210862          DOI： 10.1016/j.tetlet.2014.10.005

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  14 in total

1.  3-Anilino-4-arylmaleimides: potent and selective inhibitors of glycogen synthase kinase-3 (GSK-3).

Authors:  D G Smith; M Buffet; A E Fenwick; D Haigh; R J Ife; M Saunders; B P Slingsby; R Stacey; R W Ward
Journal:  Bioorg Med Chem Lett       Date:  2001-03-12       Impact factor: 2.823

2.  The mechanism of orotidine 5'-monophosphate decarboxylase: catalysis by destabilization of the substrate.

Authors:  W Y Feng; T J Austin; F Chew; S Gronert; W Wu
Journal:  Biochemistry       Date:  2000-02-22       Impact factor: 3.162

3.  Stability of the 6-carbanion of uracil analogues: mechanistic implications for model reactions of orotidine-5'-monophosphate decarboxylase.

Authors:  Freeman M Wong; Christina C Capule; Weiming Wu
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

4.  Accelerated decarboxylation of 1,3-dimethylorotic acid in ionic liquid.

Authors:  Freeman M Wong; Weiming Wu
Journal:  Bioorg Chem       Date:  2006-02-24       Impact factor: 5.275

5.  Synthesis of orotic acid from aspartic acid.

Authors:  J F NYC; H K MITCHELL
Journal:  J Am Chem Soc       Date:  1947-06       Impact factor: 15.419

6.  A proficient enzyme revisited: the predicted mechanism for orotidine monophosphate decarboxylase.

Authors:  J K Lee; K N Houk
Journal:  Science       Date:  1997-05-09       Impact factor: 47.728

7.  Carbanions from decarboxylation of orotate analogs: stability and mechanistic implications.

Authors:  Fong Ying Yeoh; Roxanne R Cuasito; Christina C Capule; Freeman M Wong; Weiming Wu
Journal:  Bioorg Chem       Date:  2007-04-02       Impact factor: 5.275

8.  Stabilities of Uracil and Pyridone-Based Carbanions: A Systematic Study in the Gas Phase and Solution and Implications for the Mechanism of Orotidine-5'-Monophosphate Decarboxylase.

Authors:  Nicholas A Senger; Carly E Bliss; James R Keeffe; Scott Gronert; Weiming Wu
Journal:  Tetrahedron       Date:  2013-07-01       Impact factor: 2.457

9.  Surprisingly low aqueous acidity at the alpha-positions of pyridiniums and pyrimidinium: the role of solvation.

Authors:  Freeman M Wong; Christina C Capule; David X Chen; Scott Gronert; Weiming Wu
Journal:  Org Lett       Date:  2008-06-07       Impact factor: 6.005

10.  Orotic acid decarboxylation in water and nonpolar solvents: a potential role for desolvation in the action of OMP decarboxylase.

Authors:  Charles A Lewis; Richard Wolfenden
Journal:  Biochemistry       Date:  2009-09-15       Impact factor: 3.162
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  1 in total

1.  Reductive debromination of 1,2-dibromides with anisidines.

Authors:  Kristen M McGraw; Jeannette T Bowler; Vy T Ly; Ihsan Erden; Weiming Wu
Journal:  Tetrahedron Lett       Date:  2016-01-20       Impact factor: 2.415
  1 in total

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