Synthetic, Structural, and Anticancer Activity Evaluation Studies on Novel Pyrazolylnucleosides
Identifieur interne : 000631 ( Main/Exploration ); précédent : 000630; suivant : 000632Synthetic, 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
Affiliations:
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">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><wicri:regionArea>SUN Pharmaceuticals R&D, Gurgaon, Sarhaul, Sector-18, Haryana-122 015</wicri:regionArea><wicri:noRegion>Haryana-122 015</wicri:noRegion></affiliation></author><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><wicri:noRegion>Delhi 110 021</wicri:noRegion></affiliation></author><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></author><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><wicri:noRegion>CA 94304</wicri:noRegion></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="3"><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><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName></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><wicri:noRegion>CA 94304</wicri:noRegion></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></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">31671703</idno><idno type="pmc">6864788</idno><idno 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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><wicri:regionArea>SUN Pharmaceuticals R&D, Gurgaon, Sarhaul, Sector-18, Haryana-122 015</wicri:regionArea><wicri:noRegion>Haryana-122 015</wicri:noRegion></affiliation></author><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><wicri:noRegion>Delhi 110 021</wicri:noRegion></affiliation></author><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></author><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><wicri:noRegion>CA 94304</wicri:noRegion></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="3"><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><placeName><region type="region" nuts="2">Île-de-France</region><settlement type="city">Paris</settlement></placeName></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><wicri:noRegion>CA 94304</wicri:noRegion></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></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><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><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Yates, M K" uniqKey="Yates M">M.K. Yates</name></author><author><name sortKey="Seley Radtke, K L" uniqKey="Seley Radtke K">K.L. Seley-Radtke</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Singh, S" uniqKey="Singh S">S. Singh</name></author><author><name sortKey="Bhattarai, D" uniqKey="Bhattarai D">D. 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Matsuda</name></author><author><name sortKey="Koboyashi, G" uniqKey="Koboyashi G">G. Koboyashi</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>France</li><li>Inde</li><li>États-Unis</li></country><region><li>Île-de-France</li></region><settlement><li>Paris</li></settlement></list><tree><noCountry><name sortKey="Jha, Amitabh" sort="Jha, Amitabh" uniqKey="Jha A" first="Amitabh" last="Jha">Amitabh Jha</name><name sortKey="Kaushik, Kumar" sort="Kaushik, Kumar" uniqKey="Kaushik K" first="Kumar" last="Kaushik">Kumar Kaushik</name><name sortKey="Parmar, Virinder S" sort="Parmar, Virinder S" uniqKey="Parmar V" first="Virinder S." last="Parmar">Virinder S. Parmar</name><name sortKey="Prasad, Ashok K" sort="Prasad, Ashok K" uniqKey="Prasad A" first="Ashok K." last="Prasad">Ashok K. Prasad</name><name sortKey="Wengel, Jesper" sort="Wengel, Jesper" uniqKey="Wengel J" first="Jesper" last="Wengel">Jesper Wengel</name></noCountry><country name="Inde"><noRegion><name sortKey="Yadav, Yogesh" sort="Yadav, Yogesh" uniqKey="Yadav Y" first="Yogesh" last="Yadav">Yogesh Yadav</name></noRegion><name sortKey="Sharma, Deepti" sort="Sharma, Deepti" uniqKey="Sharma D" first="Deepti" last="Sharma">Deepti Sharma</name></country><country name="États-Unis"><noRegion><name sortKey="Kumar, Vineet" sort="Kumar, Vineet" uniqKey="Kumar V" first="Vineet" last="Kumar">Vineet Kumar</name></noRegion><name sortKey="Malhotra, Sanjay V" sort="Malhotra, Sanjay V" uniqKey="Malhotra S" first="Sanjay V." last="Malhotra">Sanjay V. Malhotra</name></country><country name="France"><region name="Île-de-France"><name sortKey="Len, Christophe" sort="Len, Christophe" uniqKey="Len C" first="Christophe" last="Len">Christophe Len</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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