Literature DB >> 23930082

Synthesis of N6 ,N6-Dialkyl Adenine Nucleosides With In Situ Formed Hexaalkylphosphorus Triamides.

Mahesh K Lakshman1, Asad Choudhury, Suyeal Bae, Eliezer Rochttis, Padmanava Pradhan, Amit Kumar.   

Abstract

Reactions between secondary amines and phosphorus trichloride (PCl3) leads to the formation of the corresponding tris(dialkylamino)phosphines or hexaalkylphosphorus triamides [HAPT: (R2N)3P]. Reaction of silyl-protected 2'-deoxyinosine and acetyl-protected inosine with the in situ formed HAPT and iodine (I2) leads to the formation of N6,N6-dialkyl adenosine and 2'-deoxyadenosine. In some cases the stoichiometry of the amine is important as also the use of a tertiary amine base. The effect of amine stoichiometry on the reaction of HAPT with I2 has been studied by 31P{1H} NMR.

Entities:  

Keywords:  adenosine; amine; inosine; iodine; phosphorus triamide

Year:  2009        PMID： 23930082      PMCID： PMC3735233          DOI： 10.1002/ejoc.200800752

Source DB:  PubMed          Journal:  European J Org Chem        ISSN： 1099-0690


  45 in total

1.  Synthesis and antimalarial activity of novel N6-substituted adenosine derivatives.

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Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2003 May-Aug       Impact factor: 1.381

2.  An adenosine analog (IB-MECA) inhibits anchorage-dependent cell growth of various human breast cancer cell lines.

Authors:  Mojtaba Panjehpour; Fatemeh Karami-Tehrani
Journal:  Int J Biochem Cell Biol       Date:  2004-08       Impact factor: 5.085

3.  A novel adenosine analog, thio-Cl-IB-MECA, induces G0/G1 cell cycle arrest and apoptosis in human promyelocytic leukemia HL-60 cells.

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Journal:  Biochem Pharmacol       Date:  2005-09-15       Impact factor: 5.858

4.  Site-specific modification of the human N-ras proto-oncogene with each diol epoxide metabolite of benzo[a]pyrene and thermal denaturation studies of the adducted duplexes.

Authors:  S Chaturvedi; M K Lakshman
Journal:  Carcinogenesis       Date:  1996-12       Impact factor: 4.944

5.  Deprotonation of calixarenes in acetonitrile.

Authors:  Ian D Cunningham; Marc Woolfall
Journal:  J Org Chem       Date:  2005-11-11       Impact factor: 4.354

6.  N6-substituted D-4'-thioadenosine-5'-methyluronamides: potent and selective agonists at the human A3 adenosine receptor.

Authors:  Lak Shin Jeong; Dong Zhe Jin; Hea Ok Kim; Dae Hong Shin; Hyung Ryong Moon; Prashantha Gunaga; Moon Woo Chun; Yong-Chul Kim; Neli Melman; Zhan-Guo Gao; Kenneth A Jacobson
Journal:  J Med Chem       Date:  2003-08-28       Impact factor: 7.446

7.  Stereoselective synthesis of sugar-modified enyne analogues of adenosine and uridine. Interaction with S-adenosyl-L-homocysteine hydrolase and antiviral and cytotoxic effects.

Authors:  Stanislaw F Wnuk; Elzbieta Lewandowska; Pablo R Sacasa; Leigh N Crain; Jinsong Zhang; Ronald T Borchardt; Erik De Clercq
Journal:  J Med Chem       Date:  2004-10-07       Impact factor: 7.446

8.  A novel polymer supported approach to nucleoside modification.

Authors:  Suyeal Bae; Mahesh K Lakshman
Journal:  J Org Chem       Date:  2008-04-23       Impact factor: 4.354

9.  PURINE NUCLEOSIDES. X. THE SYNTHESIS OF CERTAIN NATURALLY OCCURRING 2-SUBSTITUTED AMINO-9-BETA-D-RIBOFURANOSYLPURIN-6(1H)-ONES (N2-SUBSTITUTED GUANOSINES).

Authors:  J F GERSTER; R K ROBINS
Journal:  J Am Chem Soc       Date:  1965-08-20       Impact factor: 15.419

10.  N6-substituted C5'-modified adenosines as A1 adenosine receptor agonists.

Authors:  T D Ashton; Stephen P Baker; Sally A Hutchinson; Peter J Scammells
Journal:  Bioorg Med Chem       Date:  2007-11-06       Impact factor: 3.641
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  5 in total

1.  One-pot etherification of purine nucleosides and pyrimidines.

Authors:  Hari Prasad Kokatla; Mahesh K Lakshman
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

2.  A simple method for C-6 modification of guanine nucleosides.

Authors:  Mahesh K Lakshman; Josh Frank
Journal:  Org Biomol Chem       Date:  2009-06-01       Impact factor: 3.876

3.  A novel bis(pinacolato)diboron-mediated N-O bond deoxygenative route to C6 benzotriazolyl purine nucleoside derivatives.

Authors:  Vikram Basava; Lijia Yang; Padmanava Pradhan; Mahesh K Lakshman
Journal:  Org Biomol Chem       Date:  2016-07-05       Impact factor: 3.876

4.  Simple Synthesis of Amides and Weinreb Amides via Use of PPh3 or Polymer-Supported PPh3 and Iodine.

Authors:  Amit Kumar; Hari Kiran Akula; Mahesh K Lakshman
Journal:  European J Org Chem       Date:  2010-05

5.  Inhibitors of adenosine consuming parasites through polymer-assisted N-acylation of N6-substituted 5'-amino-5'-deoxyadenosines.

Authors:  Vida Zohrabi-Kalantari; Philipp Heidler; Marcel Kaiser; Reto Brun; Christoph Kamper; Andreas Link
Journal:  Mol Divers       Date:  2009-06-26       Impact factor: 2.943
  5 in total

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