Synthesis and Biological Properties of C-2 Triazolylinosine Derivatives
Identifieur interne : 001299 ( Main/Exploration ); précédent : 001298; suivant : 001300Synthesis and Biological Properties of C-2 Triazolylinosine Derivatives
Auteurs : Mahesh K. Lakshman [États-Unis] ; Amit Kumar [États-Unis] ; Raghavan Balachandran [États-Unis] ; Billy W. Day [États-Unis] ; Graciela Andrei [Belgique] ; Robert Snoeck [Belgique] ; Jan Balzarini [Belgique]Source :
- The Journal of organic chemistry [ 0022-3263 ] ; 2012.
Abstract
Url:
DOI: 10.1021/jo300628y
PubMed: 22758929
PubMed Central: 3427785
Affiliations:
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Le document en format XML
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<front><div type="abstract" xml:lang="en"><p id="P1"><graphic xlink:href="nihms398666u1.jpg" position="float" orientation="portrait"></graphic>
</p>
<p id="P2"><italic>O</italic>
<sup>6</sup>
-(Benzotriazol-1<italic>H</italic>
-yl)guanosine and its 2′-deoxy analogue are readily converted to the <italic>O</italic>
<sup>6</sup>
-allyl derivatives that upon diazotization with <italic>t</italic>
-BuONO and TMS-N<sub>3</sub>
yield the C-2 azido derivatives. We have previously analyzed the solvent-dependent azide•tetrazole equilibrium of C-6 azidopurine nucleosides, and in contrast to these, the <italic>O</italic>
<sup>6</sup>
-allyl C-2 azido nucleosides appear to exist predominantly in the azido form, relatively independent of solvent polarity. In the presently described cases, the tetrazole appears to be very minor. Consistent with the presence of the azido functionality, each neat C-2 azide displayed a prominent IR band at 2126–2130 cm<sup>−1</sup>
. A screen of conditions for the ligation of the azido nucleosides with alkynes showed that CuCl in <italic>t</italic>
-BuOH/H<sub>2</sub>
O is optimal, yielding C-2 1,2,3-triazolyl nucleosides in 70–82% yields. Removal of the silyl groups with Et<sub>3</sub>
N•3HF followed by deallylation with PhSO<sub>2</sub>
Na/Pd(PPh<sub>3</sub>
)<sub>4</sub>
gave the C-2 triazolylinosine nucleosides. In a continued demonstration of the versatility of <italic>O</italic>
<sup>6</sup>
-(benzotriazol-1<italic>H</italic>
-yl)purine nucleosides, one C-2 triazolylinosine derivative was converted to two adenosine analogues via these intermediates, under mild conditions. Products were desilylated for biological assays. The two C-2 triazolyl adenosine analogues demonstrated pronounced antiproliferative activity in human ovarian and colorectal carcinoma cell cultures. When evaluated for antiviral activity against a broad spectrum of DNA and RNA viruses, some of the C-2 triazolylinosine derivatives showed modest inhibitory activity against cytomegalovirus.</p>
</div>
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<li>États-Unis</li>
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<name sortKey="Balachandran, Raghavan" sort="Balachandran, Raghavan" uniqKey="Balachandran R" first="Raghavan" last="Balachandran">Raghavan Balachandran</name>
<name sortKey="Day, Billy W" sort="Day, Billy W" uniqKey="Day B" first="Billy W." last="Day">Billy W. Day</name>
<name sortKey="Day, Billy W" sort="Day, Billy W" uniqKey="Day B" first="Billy W." last="Day">Billy W. Day</name>
<name sortKey="Kumar, Amit" sort="Kumar, Amit" uniqKey="Kumar A" first="Amit" last="Kumar">Amit Kumar</name>
</country>
<country name="Belgique"><noRegion><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name>
</noRegion>
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<name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name>
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