Synthetic, Structural, and Anticancer Activity Evaluation Studies on Novel Pyrazolylnucleosides
Identifieur interne : 000964 ( Pmc/Curation ); précédent : 000963; suivant : 000965Synthetic, Structural, and Anticancer Activity Evaluation Studies on Novel Pyrazolylnucleosides
Auteurs : Yogesh Yadav [Inde] ; Deepti Sharma [Inde] ; Kumar Kaushik ; Vineet Kumar [États-Unis] ; Amitabh Jha ; Ashok K. Prasad ; Christophe Len [France] ; Sanjay V. Malhotra [États-Unis] ; Jesper Wengel ; Virinder S. ParmarSource :
- Molecules [ 1420-3049 ] ; 2019.
Abstract
The synthesis of novel pyrazolylnucleosides
Url:
DOI: 10.3390/molecules24213922
PubMed: 31671703
PubMed Central: 6864788
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(Y.Y.);<email>iamvineet@gmail.com</email>
(V.K.);<email>ashokenzyme@gmail.com</email>
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<affiliation><nlm:aff id="af2-molecules-24-03922">Medicinal Chemistry Laboratory, Department of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada;<email>amitabh.jha@acadiau.ca</email>
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<author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name>
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</nlm:aff>
</affiliation>
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</nlm:aff>
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<author><name sortKey="Parmar, Virinder S" sort="Parmar, Virinder S" uniqKey="Parmar V" first="Virinder S." last="Parmar">Virinder S. Parmar</name>
<affiliation><nlm:aff id="af1-molecules-24-03922">Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India;<email>yogeshyadav77@gmail.com</email>
(Y.Y.);<email>iamvineet@gmail.com</email>
(V.K.);<email>ashokenzyme@gmail.com</email>
(A.K.P.)</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="af5-molecules-24-03922">Department of Chemistry and Environmental Science, Medgar Evers College, The City University of New York, 1638 Bedford Avenue, Brooklyn, NY 11225, USA;<email>kumar.kaushik.drdo@gmail.com</email>
</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="af9-molecules-24-03922">Nucleic Acid Center, Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, DK-5230 Odense, Denmark;<email>jwe@sdu.dk</email>
</nlm:aff>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Synthetic, Structural, and Anticancer Activity Evaluation Studies on Novel Pyrazolylnucleosides</title>
<author><name sortKey="Yadav, Yogesh" sort="Yadav, Yogesh" uniqKey="Yadav Y" first="Yogesh" last="Yadav">Yogesh Yadav</name>
<affiliation><nlm:aff id="af1-molecules-24-03922">Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India;<email>yogeshyadav77@gmail.com</email>
(Y.Y.);<email>iamvineet@gmail.com</email>
(V.K.);<email>ashokenzyme@gmail.com</email>
(A.K.P.)</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="af2-molecules-24-03922">Medicinal Chemistry Laboratory, Department of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada;<email>amitabh.jha@acadiau.ca</email>
</nlm:aff>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="af3-molecules-24-03922">SUN Pharmaceuticals R&D, Gurgaon, Sarhaul, Sector-18, Haryana-122 015, India</nlm:aff>
<country xml:lang="fr">Inde</country>
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<author><name sortKey="Sharma, Deepti" sort="Sharma, Deepti" uniqKey="Sharma D" first="Deepti" last="Sharma">Deepti Sharma</name>
<affiliation><nlm:aff id="af1-molecules-24-03922">Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India;<email>yogeshyadav77@gmail.com</email>
(Y.Y.);<email>iamvineet@gmail.com</email>
(V.K.);<email>ashokenzyme@gmail.com</email>
(A.K.P.)</nlm:aff>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="af4-molecules-24-03922">Sri Venkateswara College, Benito Juarez Road, Dhaula Kuan, University of Delhi, Delhi 110 021, India</nlm:aff>
<country xml:lang="fr">Inde</country>
<wicri:regionArea>Sri Venkateswara College, Benito Juarez Road, Dhaula Kuan, University of Delhi, Delhi 110 021</wicri:regionArea>
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<author><name sortKey="Kaushik, Kumar" sort="Kaushik, Kumar" uniqKey="Kaushik K" first="Kumar" last="Kaushik">Kumar Kaushik</name>
<affiliation><nlm:aff id="af5-molecules-24-03922">Department of Chemistry and Environmental Science, Medgar Evers College, The City University of New York, 1638 Bedford Avenue, Brooklyn, NY 11225, USA;<email>kumar.kaushik.drdo@gmail.com</email>
</nlm:aff>
</affiliation>
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<author><name sortKey="Kumar, Vineet" sort="Kumar, Vineet" uniqKey="Kumar V" first="Vineet" last="Kumar">Vineet Kumar</name>
<affiliation><nlm:aff id="af1-molecules-24-03922">Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India;<email>yogeshyadav77@gmail.com</email>
(Y.Y.);<email>iamvineet@gmail.com</email>
(V.K.);<email>ashokenzyme@gmail.com</email>
(A.K.P.)</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="af6-molecules-24-03922">Laboratory of Synthetic Chemistry, Leidos Biomedical Research Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 2170, USA;<email>smalhotra@stanford.edu</email>
</nlm:aff>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="af7-molecules-24-03922">Department of Radiation Oncology, Stanford University, 1050A Arastradero Road, A252, Palo Alto, CA 94304, USA</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>Department of Radiation Oncology, Stanford University, 1050A Arastradero Road, A252, Palo Alto, CA 94304</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Jha, Amitabh" sort="Jha, Amitabh" uniqKey="Jha A" first="Amitabh" last="Jha">Amitabh Jha</name>
<affiliation><nlm:aff id="af2-molecules-24-03922">Medicinal Chemistry Laboratory, Department of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada;<email>amitabh.jha@acadiau.ca</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Prasad, Ashok K" sort="Prasad, Ashok K" uniqKey="Prasad A" first="Ashok K." last="Prasad">Ashok K. Prasad</name>
<affiliation><nlm:aff id="af1-molecules-24-03922">Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India;<email>yogeshyadav77@gmail.com</email>
(Y.Y.);<email>iamvineet@gmail.com</email>
(V.K.);<email>ashokenzyme@gmail.com</email>
(A.K.P.)</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name>
<affiliation wicri:level="1"><nlm:aff id="af8-molecules-24-03922">Chimie ParisTech, PSL University, CNRS Institute of Chemistry for Life and Health Sciences—i-CLeHS, 11 rue Pierre et Marie Curie, F-75005 Paris, France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea>Chimie ParisTech, PSL University, CNRS Institute of Chemistry for Life and Health Sciences—i-CLeHS, 11 rue Pierre et Marie Curie, F-75005 Paris</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Malhotra, Sanjay V" sort="Malhotra, Sanjay V" uniqKey="Malhotra S" first="Sanjay V." last="Malhotra">Sanjay V. Malhotra</name>
<affiliation><nlm:aff id="af6-molecules-24-03922">Laboratory of Synthetic Chemistry, Leidos Biomedical Research Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 2170, USA;<email>smalhotra@stanford.edu</email>
</nlm:aff>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="af7-molecules-24-03922">Department of Radiation Oncology, Stanford University, 1050A Arastradero Road, A252, Palo Alto, CA 94304, USA</nlm:aff>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>Department of Radiation Oncology, Stanford University, 1050A Arastradero Road, A252, Palo Alto, CA 94304</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Wengel, Jesper" sort="Wengel, Jesper" uniqKey="Wengel J" first="Jesper" last="Wengel">Jesper Wengel</name>
<affiliation><nlm:aff id="af9-molecules-24-03922">Nucleic Acid Center, Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, DK-5230 Odense, Denmark;<email>jwe@sdu.dk</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Parmar, Virinder S" sort="Parmar, Virinder S" uniqKey="Parmar V" first="Virinder S." last="Parmar">Virinder S. Parmar</name>
<affiliation><nlm:aff id="af1-molecules-24-03922">Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India;<email>yogeshyadav77@gmail.com</email>
(Y.Y.);<email>iamvineet@gmail.com</email>
(V.K.);<email>ashokenzyme@gmail.com</email>
(A.K.P.)</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="af5-molecules-24-03922">Department of Chemistry and Environmental Science, Medgar Evers College, The City University of New York, 1638 Bedford Avenue, Brooklyn, NY 11225, USA;<email>kumar.kaushik.drdo@gmail.com</email>
</nlm:aff>
</affiliation>
<affiliation><nlm:aff id="af9-molecules-24-03922">Nucleic Acid Center, Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, DK-5230 Odense, Denmark;<email>jwe@sdu.dk</email>
</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">Molecules</title>
<idno type="eISSN">1420-3049</idno>
<imprint><date when="2019">2019</date>
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<front><div type="abstract" xml:lang="en"><p>The synthesis of novel pyrazolylnucleosides <bold>3a</bold>
–<bold>e</bold>
, <bold>4a</bold>
–<bold>e</bold>
, <bold>5a</bold>
–<bold>e</bold>
, and <bold>6a</bold>
–<bold>e</bold>
are described. The structures of the regioisomers were elucidated by using extensive NMR studies. The pyrazolylnucleosides <bold>5a</bold>
–<bold>e</bold>
and <bold>6a</bold>
–<bold>e</bold>
were screened for anticancer activities on sixty human tumor cell lines. The compound <bold>6e</bold>
showed good activity against 39 cancer cell lines. In particular, it showed significant inhibition against the lung cancer cell line Hop-92 (GI<sub>50</sub>
9.3 µM) and breast cancer cell line HS 578T (GI<sub>50</sub>
3.0 µM).</p>
</div>
</front>
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<pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Molecules</journal-id>
<journal-id journal-id-type="iso-abbrev">Molecules</journal-id>
<journal-id journal-id-type="publisher-id">molecules</journal-id>
<journal-title-group><journal-title>Molecules</journal-title>
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<issn pub-type="epub">1420-3049</issn>
<publisher><publisher-name>MDPI</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">31671703</article-id>
<article-id pub-id-type="pmc">6864788</article-id>
<article-id pub-id-type="doi">10.3390/molecules24213922</article-id>
<article-id pub-id-type="publisher-id">molecules-24-03922</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Article</subject>
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</article-categories>
<title-group><article-title>Synthetic, Structural, and Anticancer Activity Evaluation Studies on Novel Pyrazolylnucleosides</article-title>
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</contrib>
<contrib contrib-type="author"><name><surname>Parmar</surname>
<given-names>Virinder S.</given-names>
</name>
<xref ref-type="aff" rid="af1-molecules-24-03922">1</xref>
<xref ref-type="aff" rid="af5-molecules-24-03922">5</xref>
<xref ref-type="aff" rid="af9-molecules-24-03922">9</xref>
<xref rid="c1-molecules-24-03922" ref-type="corresp">*</xref>
</contrib>
</contrib-group>
<aff id="af1-molecules-24-03922"><label>1</label>
Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India;<email>yogeshyadav77@gmail.com</email>
(Y.Y.);<email>iamvineet@gmail.com</email>
(V.K.);<email>ashokenzyme@gmail.com</email>
(A.K.P.)</aff>
<aff id="af2-molecules-24-03922"><label>2</label>
Medicinal Chemistry Laboratory, Department of Chemistry, Acadia University, Wolfville, NS B4P 2R6, Canada;<email>amitabh.jha@acadiau.ca</email>
</aff>
<aff id="af3-molecules-24-03922"><label>3</label>
SUN Pharmaceuticals R&D, Gurgaon, Sarhaul, Sector-18, Haryana-122 015, India</aff>
<aff id="af4-molecules-24-03922"><label>4</label>
Sri Venkateswara College, Benito Juarez Road, Dhaula Kuan, University of Delhi, Delhi 110 021, India</aff>
<aff id="af5-molecules-24-03922"><label>5</label>
Department of Chemistry and Environmental Science, Medgar Evers College, The City University of New York, 1638 Bedford Avenue, Brooklyn, NY 11225, USA;<email>kumar.kaushik.drdo@gmail.com</email>
</aff>
<aff id="af6-molecules-24-03922"><label>6</label>
Laboratory of Synthetic Chemistry, Leidos Biomedical Research Inc., Frederick National Laboratory for Cancer Research, Frederick, MD 2170, USA;<email>smalhotra@stanford.edu</email>
</aff>
<aff id="af7-molecules-24-03922"><label>7</label>
Department of Radiation Oncology, Stanford University, 1050A Arastradero Road, A252, Palo Alto, CA 94304, USA</aff>
<aff id="af8-molecules-24-03922"><label>8</label>
Chimie ParisTech, PSL University, CNRS Institute of Chemistry for Life and Health Sciences—i-CLeHS, 11 rue Pierre et Marie Curie, F-75005 Paris, France</aff>
<aff id="af9-molecules-24-03922"><label>9</label>
Nucleic Acid Center, Department of Physics, Chemistry and Pharmacy, University of Southern Denmark, Campusvej 55, DK-5230 Odense, Denmark;<email>jwe@sdu.dk</email>
</aff>
<author-notes><corresp id="c1-molecules-24-03922"><label>*</label>
Correspondence: <email>christophe.len@chimieparistech.psl.eu</email>
(C.L.); <email>vparmar@mec.cuny.edu</email>
(V.S.P.); Tel.: +33-(0)638-500-976 (C.L.); Fax: +33-(0)344-971-591 (C.L.)</corresp>
</author-notes>
<pub-date pub-type="epub"><day>30</day>
<month>10</month>
<year>2019</year>
</pub-date>
<pub-date pub-type="collection"><month>11</month>
<year>2019</year>
</pub-date>
<volume>24</volume>
<issue>21</issue>
<elocation-id>3922</elocation-id>
<history><date date-type="received"><day>13</day>
<month>9</month>
<year>2019</year>
</date>
<date date-type="accepted"><day>28</day>
<month>10</month>
<year>2019</year>
</date>
</history>
<permissions><copyright-statement>© 2019 by the authors.</copyright-statement>
<copyright-year>2019</copyright-year>
<license license-type="open-access"><license-p>Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (<ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>
).</license-p>
</license>
</permissions>
<abstract><p>The synthesis of novel pyrazolylnucleosides <bold>3a</bold>
–<bold>e</bold>
, <bold>4a</bold>
–<bold>e</bold>
, <bold>5a</bold>
–<bold>e</bold>
, and <bold>6a</bold>
–<bold>e</bold>
are described. The structures of the regioisomers were elucidated by using extensive NMR studies. The pyrazolylnucleosides <bold>5a</bold>
–<bold>e</bold>
and <bold>6a</bold>
–<bold>e</bold>
were screened for anticancer activities on sixty human tumor cell lines. The compound <bold>6e</bold>
showed good activity against 39 cancer cell lines. In particular, it showed significant inhibition against the lung cancer cell line Hop-92 (GI<sub>50</sub>
9.3 µM) and breast cancer cell line HS 578T (GI<sub>50</sub>
3.0 µM).</p>
</abstract>
<kwd-group><kwd>pyrazolylnucleosides</kwd>
<kwd>modified nucleosides</kwd>
<kwd>NOESY study</kwd>
<kwd>anticancer</kwd>
<kwd>NCI-60</kwd>
</kwd-group>
</article-meta>
</front>
</pmc>
</record>
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