Literature DB >> 18797498

Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds.

Arjun Raghuraman1, Muhammad Riaz, Michael Hindle, Umesh R Desai.   

Abstract

Sulfation of multiply hydroxylated small organic molecules is fraught with problems of poor yield, multitude of products and long reaction times. We have developed a rapid microwave-based method for synthesis of highly sulfated small organic molecules, which affords the per-sulfated product in moderate to excellent yields and high purity. The method is expected to be of value in the discovery of per-sulfated organic molecules as mimics of glycosaminoglycans, which are being increasingly recognized as modulators of key physiological functions.

Entities:  

Year:  2007        PMID: 18797498      PMCID: PMC2084256          DOI: 10.1016/j.tetlet.2007.07.100

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


  15 in total

Review 1.  The impact of microwave synthesis on drug discovery.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Nat Rev Drug Discov       Date:  2006-01       Impact factor: 84.694

2.  Synthesis of 48 disaccharide building blocks for the assembly of a heparin and heparan sulfate oligosaccharide library.

Authors:  Lung-Dai Lu; Chi-Rung Shie; Suvarn S Kulkarni; Guan-Rong Pan; Xin-An Lu; Shang-Cheng Hung
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

3.  Sulfation patterns of glycosaminoglycans encode molecular recognition and activity.

Authors:  Cristal I Gama; Sarah E Tully; Naoki Sotogaku; Peter M Clark; Manish Rawat; Nagarajan Vaidehi; William A Goddard; Akinori Nishi; Linda C Hsieh-Wilson
Journal:  Nat Chem Biol       Date:  2006-07-30       Impact factor: 15.040

4.  Novel chemo-enzymatic oligomers of cinnamic acids as direct and indirect inhibitors of coagulation proteinases.

Authors:  Bernhard H Monien; Brian L Henry; Arjun Raghuraman; Michael Hindle; Umesh R Desai
Journal:  Bioorg Med Chem       Date:  2006-08-17       Impact factor: 3.641

5.  A comprehensive approach to the synthesis of sulfate esters.

Authors:  Levi S Simpson; Theodore S Widlanski
Journal:  J Am Chem Soc       Date:  2006-02-08       Impact factor: 15.419

6.  Orthogonal sulfation strategy for synthetic heparan sulfate ligands.

Authors:  Ren-Hua Fan; Jihane Achkar; Jesús M Hernández-Torres; Alexander Wei
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

7.  Capillary electrophoresis of highly sulfated flavanoids and flavonoids.

Authors:  Mandakini Dantuluri; Gunnar T Gunnarsson; Muhammad Riaz; Huyen Nguyen; Umesh R Desai
Journal:  Anal Biochem       Date:  2005-01-15       Impact factor: 3.365

8.  Interaction of designed sulfated flavanoids with antithrombin: lessons on the design of organic activators.

Authors:  Gunnar T Gunnarsson; Umesh R Desai
Journal:  J Med Chem       Date:  2002-09-26       Impact factor: 7.446

9.  Modular synthesis of heparin oligosaccharides.

Authors:  Hernán A Orgueira; Alessandra Bartolozzi; Peter Schell; Remy E J N Litjens; Emma R Palmacci; Peter H Seeberger
Journal:  Chemistry       Date:  2003-01-03       Impact factor: 5.236

10.  Synthesis and antiviral activity of sulfated and acetylated derivatives of 2beta,3alpha-dihydroxy-5alpha-cholestane.

Authors:  Gustavo A Garrido Santos; Ana P Murray; Carlos A Pujol; Elsa B Damonte; Marta S Maier
Journal:  Steroids       Date:  2003-02       Impact factor: 2.668

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  22 in total

1.  Sulfoform generation from an orthogonally protected disaccharide.

Authors:  Runhui Liu; Oscar Morales-Collazo; Alexander Wei
Journal:  Carbohydr Res       Date:  2012-04-21       Impact factor: 2.104

2.  Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites.

Authors:  Juma Hoshino; Eun-Jung Park; Tamara P Kondratyuk; Laura Marler; John M Pezzuto; Richard B van Breemen; Shunyan Mo; Yongchao Li; Mark Cushman
Journal:  J Med Chem       Date:  2010-07-08       Impact factor: 7.446

Review 3.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

4.  Discovery of novel sulfonated small molecules that inhibit vascular tube formation.

Authors:  Karthik Raman; Rajesh Karuturi; Vimal P Swarup; Umesh R Desai; Balagurunathan Kuberan
Journal:  Bioorg Med Chem Lett       Date:  2012-04-16       Impact factor: 2.823

5.  Chemical Sulfation of Small Molecules - Advances and Challenges.

Authors:  Rami A Al-Horani; Umesh R Desai
Journal:  Tetrahedron       Date:  2010-04-17       Impact factor: 2.457

6.  On designing non-saccharide, allosteric activators of antithrombin.

Authors:  Arjun Raghuraman; Aiye Liang; Chandravel Krishnasamy; Trish Lauck; Gunnar T Gunnarsson; Umesh R Desai
Journal:  Eur J Med Chem       Date:  2008-10-09       Impact factor: 6.514

7.  Discovery of allosteric modulators of factor XIa by targeting hydrophobic domains adjacent to its heparin-binding site.

Authors:  Rajesh Karuturi; Rami A Al-Horani; Shrenik C Mehta; David Gailani; Umesh R Desai
Journal:  J Med Chem       Date:  2013-03-18       Impact factor: 7.446

8.  Designing allosteric regulators of thrombin. Exosite 2 features multiple subsites that can be targeted by sulfated small molecules for inducing inhibition.

Authors:  Preetpal Singh Sidhu; May H Abdel Aziz; Aurijit Sarkar; Akul Y Mehta; Qibing Zhou; Umesh R Desai
Journal:  J Med Chem       Date:  2013-06-13       Impact factor: 7.446

9.  Sulfated pentagalloylglucoside is a potent, allosteric, and selective inhibitor of factor XIa.

Authors:  Rami A Al-Horani; Pooja Ponnusamy; Akul Y Mehta; David Gailani; Umesh R Desai
Journal:  J Med Chem       Date:  2013-01-28       Impact factor: 7.446

10.  Capillary electrophoretic study of small, highly sulfated, non-sugar molecules interacting with antithrombin.

Authors:  Aiye Liang; Arjun Raghuraman; Umesh R Desai
Journal:  Electrophoresis       Date:  2009-05       Impact factor: 3.535

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