scholarly journals Pyrimidine Nucleosides with a Reactive (β-Chlorovinyl)sulfone or (β-Keto)sulfone Group at the C5 Position, Their Reactions with Nucleophiles and Electrophiles, and Their Polymerase-Catalyzed Incorporation into DNA

ACS Omega ◽  
2018 ◽  
Vol 3 (4) ◽  
pp. 4276-4288 ◽  
Author(s):  
Sazzad H. Suzol ◽  
A. Hasan Howlader ◽  
Zhiwei Wen ◽  
Yaou Ren ◽  
Eduardo E. Laverde ◽  
...  
Keyword(s):  
Pyrimidine Nucleosides ◽  
Sulfone Group ◽  
Reactions With Nucleophiles

Bifluoride Ion Mediated SuFEx Trifluoromethylation of Sulfonyl Fluorides and Iminosulfur Oxydifluorides

2018 ◽  
Author(s):  
Christopher J. Smedley ◽  
Bing Gao ◽  
Suhua Li ◽  
Qinheng Zheng ◽  
Andrew Molino ◽  
...  
Keyword(s):  
Breast Cancer Cells ◽  
Catalytic Mechanism ◽  
Bioactive Molecules ◽  
Chromatographic Purification ◽  
Rapid Exchange ◽  
Nucleophilic Displacement ◽  
Sulfur Fluoride ◽  
Reactions With Nucleophiles ◽  
New Generation ◽  
Selection Of

Sulfur-Fluoride Exchange (SuFEx) is the new generation click chemistry transformation exploiting the unique properties of S-F bonds and their ability to undergo near-perfect reactions with nucleophiles. We report here the first SuFEx based protocol for the efficient synthesis of pharmaceutically important triflones and bis(trifluoromethyl)sulfur oxyimines from the corresponding sulfonyl fluorides and iminosulfur oxydifluorides, respectively. The new protocol involves the rapid exchange of the S-F bond with trifluoromethyltrimethylsilane (TMSCF<sub>3</sub>) upon activation with potassium bifluoride in anhydrous DMSO. The reaction tolerates a wide selection of substrates and proceeds under mild conditions without need for chromatographic purification. A tentative catalytic mechanism is proposed supported by DFT calculations, involving formation of the free trifluoromethyl anion followed by nucleophilic displacement of the S-F through a five-coordinate intermediate. The preparation of a benzothiazole derived bis(trifluoromethyl)sulfur oxyimine with cytotoxic selectivity for MCF7 breast cancer cells demonstrates the utility of this methodology for the late-stage functionalization of bioactive molecules.<br>

The Synthesis of Novel 5-Trifluoroethoxy Pyrimidine Nucleosides

1990 ◽  
Vol 9 (6) ◽  
pp. 861-873 ◽  
Author(s):  
P. Kumar ◽  
L. I. Wiebe
Keyword(s):  
Pyrimidine Nucleosides

scholarly journals THE IONIZATION OF PYRIMIDINES IN RELATION TO THE STRUCTURE OF PYRIMIDINE NUCLEOSIDES

1926 ◽  
Vol 70 (1) ◽  
pp. 229-241
Author(s):  
P.A. Levene ◽  
Lawrence W. Bass ◽  
H.S. Simms
Keyword(s):  
Pyrimidine Nucleosides

scholarly journals 2’‐Derivatisation of 3’‐C‐methyl pyrimidine nucleosides

2021 ◽  
Author(s):  
Sarah Couturier ◽  
Suzanne Peyrottes ◽  
Christian Périgaud
Keyword(s):  
Pyrimidine Nucleosides

Synthesis of 5,7-dihydroxynaphthoquinone derivatives and their reactions with nucleophiles: Nitration of 2,3-dimethylnaphthalene and subsequent transformations

1976 ◽  
Vol 29 (10) ◽  
pp. 2247 ◽  
Author(s):  
HJ Banks ◽  
DW Cameron ◽  
MJ Crossley ◽  
EL Samuel
Keyword(s):  
Unusual Reaction ◽  
Nitro Derivatives ◽  
Reactions With Nucleophiles ◽  
Derivatives Of ◽  
Related Compounds ◽  
Benzenoid Ring

5,7-Dihydroxy-2,3-dimethyl-l,4-naphthoquinone (5) and related compounds have been synthesized. The quinone affords an accessible substrate for studying an unusual reaction with nucleophiles, which involves attack at the 8-position, i.e. at the benzenoid ring. An unsuccessful approach to (5) has led to tri- and tetra-nitro derivatives of 2,3-dimethylnaphthalene. Reduction of the former and subsequent conversions have given aminonaphthoquinone and perimidinone derivatives.

Pyrimidine nucleosides. 6. Synthesis and anticancer activities of N4-substituted 2,2'-anhydronucleosides

1974 ◽  
Vol 17 (10) ◽  
pp. 1076-1078 ◽  
Author(s):  
Tadashi Kanai ◽  
Motonobu Ichino ◽  
Akio Hoshi ◽  
Fumihiko Kanzawa ◽  
Kazuo Kuretani
Keyword(s):  
Anticancer Activities ◽  
Pyrimidine Nucleosides

Diels-Alder-Adducts of Dichloromethylenepropanedinitrile; Reactions with Nucleophiles

2000 ◽  
Vol 342 (8) ◽  
pp. 819-824 ◽  
Author(s):  
Klaus Friedrich ◽  
Karl Bechtold ◽  
Leo Willin ◽  
Hans Fritz
Keyword(s):  
Diels Alder ◽  
Reactions With Nucleophiles
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