N ′-[4-[(Substituted imino)methyl]benzylidene]-substituted benzohydrazides: synthesis, antimicrobial, antiviral, and anticancer evaluation, and QSAR studies
Identifieur interne : 001354 ( Main/Merge ); précédent : 001353; suivant : 001355N ′-[4-[(Substituted imino)methyl]benzylidene]-substituted benzohydrazides: synthesis, antimicrobial, antiviral, and anticancer evaluation, and QSAR studies
Auteurs : Pradeep Kumar [Inde] ; Balasubramanian Narasimhan [Inde] ; Kalavathy Ramasamy [Malaisie] ; Vasudevan Mani [Malaisie] ; Rakesh Kumar Mishra [Malaisie] ; Abu Bakar Abdul Majeed [Malaisie] ; Erik De Clercq [Belgique]Source :
- Monatshefte für Chemie - Chemical Monthly [ 0026-9247 ] ; 2013-06-01.
English descriptors
- KwdEn :
Abstract
Abstract: A variety of N′-[4-[(substituted imino)methyl]benzylidene]-substituted benzohydrazides have been synthesized and evaluated for antimicrobial and anticancer potential. Results from testing of antimicrobial activity indicated the most potent antimicrobial agents had pMIC am = 1.51. The synthesized compounds were bacteriostatic and fungistatic in action. Results from evaluation of antiviral activity indicated that none of the synthesized hydrazide derivatives inhibited viral replication at sub-toxic concentrations. Results from anti-HIV screening against HIV-2 strain ROD indicated that one compound was more potent (IC 50 ≥ 1 μg/cm3) than the standard drug nevirapine (IC 50 ≥ 4 μg/cm3) and another was equipotent (IC 50 ≥ 4 μg/cm3). The most effective anticancer agent against both HCT116 and MCF7 cancer cell lines had IC 50 = 19 and 18 μg/cm3, respectively. QSAR analysis indicated the importance of Wiener index (W) and energy of the lowest unoccupied molecular orbital (LUMO) in describing the antimicrobial activity of the synthesized compounds. Graphical Abstract:
Url:
- https://api.istex.fr/ark:/67375/VQC-8Q1BSZQT-C/fulltext.pdf
- http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7087754
DOI: 10.1007/s00706-012-0877-3
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ISTEX:A7221A391646EA1CA9D8C0BCFED98DD9875DABDALe document en format XML
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Louvain</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmc">7087754</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7087754</idno><idno type="RBID">PMC:7087754</idno><idno type="doi">10.1007/s00706-012-0877-3</idno><idno type="pmid">NONE</idno><date when="2012">2012</date><idno type="wicri:Area/Pmc/Corpus">000307</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000307</idno><idno type="wicri:Area/Pmc/Curation">000307</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000307</idno><idno type="wicri:Area/Pmc/Checkpoint">000773</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000773</idno><idno type="wicri:Area/Ncbi/Merge">001699</idno><idno type="wicri:Area/Ncbi/Curation">001699</idno><idno type="wicri:Area/Ncbi/Checkpoint">001699</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main"><italic>N</italic>′-[4-[(Substituted imino)methyl]benzylidene]-substituted benzohydrazides: synthesis, antimicrobial, antiviral, and anticancer evaluation, and QSAR studies</title><author><name sortKey="Kumar, Pradeep" sort="Kumar, Pradeep" uniqKey="Kumar P" first="Pradeep" last="Kumar">Pradeep Kumar</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.411524.7</institution-id><institution-id institution-id-type="ISNI">0000000417902262</institution-id><institution>Faculty of Pharmaceutical Sciences,</institution><institution>Maharshi Dayanand University,</institution></institution-wrap>Rohtak, 124001 India</nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea>Rohtak</wicri:regionArea></affiliation></author><author><name sortKey="Narasimhan, Balasubramanian" sort="Narasimhan, Balasubramanian" uniqKey="Narasimhan B" first="Balasubramanian" last="Narasimhan">Balasubramanian Narasimhan</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="GRID">grid.411524.7</institution-id><institution-id institution-id-type="ISNI">0000000417902262</institution-id><institution>Faculty of Pharmaceutical Sciences,</institution><institution>Maharshi Dayanand University,</institution></institution-wrap>Rohtak, 124001 India</nlm:aff><country xml:lang="fr">Inde</country><wicri:regionArea>Rohtak</wicri:regionArea></affiliation></author><author><name sortKey="Ramasamy, Kalavathy" sort="Ramasamy, Kalavathy" uniqKey="Ramasamy K" first="Kalavathy" last="Ramasamy">Kalavathy Ramasamy</name><affiliation><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="GRID">grid.412259.9</institution-id><institution-id institution-id-type="ISNI">0000000121611343</institution-id><institution>Collaborative Drug Discovery Research Group, Faculty of Pharmacy, Campus Puncak Alam,</institution><institution>Universiti Teknologi MARA (UiTM),</institution></institution-wrap>Bandar Puncak Alam, 42300 Shan Alam, Selangor Malaysia</nlm:aff><wicri:noCountry code="subfield">Selangor Malaysia</wicri:noCountry></affiliation></author><author><name sortKey="Mani, Vasudevan" sort="Mani, Vasudevan" uniqKey="Mani V" first="Vasudevan" last="Mani">Vasudevan Mani</name><affiliation><nlm:aff id="Aff3"><institution-wrap><institution-id institution-id-type="GRID">grid.412259.9</institution-id><institution-id institution-id-type="ISNI">0000000121611343</institution-id><institution>Brain Research Laboratory, Faculty of Pharmacy, Campus Puncak Alam,</institution><institution>Universiti Teknologi MARA (UiTM),</institution></institution-wrap>Bandar Puncak Alam, 42300 Shan Alam, Selangor Malaysia</nlm:aff><wicri:noCountry code="subfield">Selangor Malaysia</wicri:noCountry></affiliation></author><author><name sortKey="Mishra, Rakesh Kumar" sort="Mishra, Rakesh Kumar" uniqKey="Mishra R" first="Rakesh Kumar" last="Mishra">Rakesh Kumar Mishra</name><affiliation><nlm:aff id="Aff3"><institution-wrap><institution-id institution-id-type="GRID">grid.412259.9</institution-id><institution-id institution-id-type="ISNI">0000000121611343</institution-id><institution>Brain Research Laboratory, Faculty of Pharmacy, Campus Puncak Alam,</institution><institution>Universiti Teknologi MARA (UiTM),</institution></institution-wrap>Bandar Puncak Alam, 42300 Shan Alam, Selangor Malaysia</nlm:aff><wicri:noCountry code="subfield">Selangor Malaysia</wicri:noCountry></affiliation></author><author><name sortKey="Majeed, Abu Bakar Abdul" sort="Majeed, Abu Bakar Abdul" uniqKey="Majeed A" first="Abu Bakar Abdul" last="Majeed">Abu Bakar Abdul Majeed</name><affiliation><nlm:aff id="Aff3"><institution-wrap><institution-id institution-id-type="GRID">grid.412259.9</institution-id><institution-id institution-id-type="ISNI">0000000121611343</institution-id><institution>Brain Research Laboratory, Faculty of Pharmacy, Campus Puncak Alam,</institution><institution>Universiti Teknologi MARA (UiTM),</institution></institution-wrap>Bandar Puncak Alam, 42300 Shan Alam, Selangor Malaysia</nlm:aff><wicri:noCountry code="subfield">Selangor Malaysia</wicri:noCountry></affiliation></author><author><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><affiliation wicri:level="3"><nlm:aff id="Aff4"><institution-wrap><institution-id institution-id-type="GRID">grid.415751.3</institution-id><institution>Laboratory of Virology and Chemotherapy,</institution><institution>Rega Institute for Medical Research,</institution></institution-wrap>Minderbroedersstraat 10, 3000 Louvain, Belgium</nlm:aff><country xml:lang="fr">Belgique</country><wicri:regionArea>Minderbroedersstraat 10, 3000 Louvain</wicri:regionArea><placeName><region type="province" nuts="2">Province du Brabant flamand</region><settlement type="city">Louvain</settlement></placeName></affiliation></author></analytic><series><title level="j">Monatshefte Fur Chemie</title><idno type="ISSN">0026-9247</idno><idno type="eISSN">1434-4475</idno><imprint><date when="2012">2012</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><sec><title>Abstract</title><p>A variety of <italic>N</italic>′-[4-[(substituted imino)methyl]benzylidene]-substituted benzohydrazides have been synthesized and evaluated for antimicrobial and anticancer potential. Results from testing of antimicrobial activity indicated the most potent antimicrobial agents had p<italic>MIC</italic><sub>am</sub> = 1.51. The synthesized compounds were bacteriostatic and fungistatic in action. Results from evaluation of antiviral activity indicated that none of the synthesized hydrazide derivatives inhibited viral replication at sub-toxic concentrations. Results from anti-HIV screening against HIV-2 strain ROD indicated that one compound was more potent (<italic>IC</italic><sub>50</sub> ≥ 1 μg/cm<sup>3</sup>) than the standard drug nevirapine (<italic>IC</italic><sub>50</sub> ≥ 4 μg/cm<sup>3</sup>) and another was equipotent (<italic>IC</italic><sub>50</sub> ≥ 4 μg/cm<sup>3</sup>). The most effective anticancer agent against both HCT116 and MCF7 cancer cell lines had <italic>IC</italic><sub>50</sub> = 19 and 18 μg/cm<sup>3</sup>, respectively. QSAR analysis indicated the importance of Wiener index (<italic>W</italic>) and energy of the lowest unoccupied molecular orbital (LUMO) in describing the antimicrobial activity of the synthesized compounds.</p></sec><sec><title>Graphical Abstract</title><p><graphic position="anchor" xlink:href="706_2012_877_Figa_HTML" id="MO1"></graphic></p></sec></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Metwally, Ka" uniqKey="Metwally K">KA Metwally</name></author><author><name sortKey="Abdel Aziz, Lm" uniqKey="Abdel Aziz L">LM Abdel-Aziz</name></author><author><name sortKey="Lashine, Esm" uniqKey="Lashine E">ESM Lashine</name></author><author><name sortKey="Husseiny, Mi" uniqKey="Husseiny M">MI Husseiny</name></author><author><name sortKey="Badawy, Rh" uniqKey="Badawy R">RH Badawy</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Banerjee, D" uniqKey="Banerjee D">D Banerjee</name></author><author><name 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Uriarte</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Golbraikh, A" uniqKey="Golbraikh A">A Golbraikh</name></author><author><name sortKey="Tropsha, A" uniqKey="Tropsha A">A Tropsha</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kim, Ym" uniqKey="Kim Y">YM Kim</name></author><author><name sortKey="Farrah, S" uniqKey="Farrah S">S Farrah</name></author><author><name sortKey="Baney, Rh" uniqKey="Baney R">RH Baney</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kumar, A" uniqKey="Kumar A">A Kumar</name></author><author><name sortKey="Narasimhan, B" uniqKey="Narasimhan B">B Narasimhan</name></author><author><name sortKey="Kumar, D" uniqKey="Kumar D">D Kumar</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Kier, Lb" uniqKey="Kier L">LB Kier</name></author><author><name sortKey="Hall, Lh" uniqKey="Hall L">LH Hall</name></author></analytic></biblStruct><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="Bajaj, S" uniqKey="Bajaj S">S Bajaj</name></author><author><name sortKey="Sambi, Ss" uniqKey="Sambi S">SS Sambi</name></author><author><name sortKey="Madan, Ak" uniqKey="Madan A">AK Madan</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Narasimhan, B" uniqKey="Narasimhan B">B Narasimhan</name></author><author><name sortKey="Judge, V" uniqKey="Judge V">V Judge</name></author><author><name sortKey="Narang, R" uniqKey="Narang R">R Narang</name></author><author><name sortKey="Ohlan, S" uniqKey="Ohlan S">S Ohlan</name></author><author><name sortKey="Ohlan, R" uniqKey="Ohlan R">R Ohlan</name></author></analytic></biblStruct><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="Rodriguez Arguelles, Mc" uniqKey="Rodriguez Arguelles M">MC Rodriguez-Arguelles</name></author><author><name sortKey="Lopez Silva, Ec" uniqKey="Lopez Silva E">EC Lopez-Silva</name></author><author><name sortKey="Sanmartin, J" uniqKey="Sanmartin J">J Sanmartin</name></author><author><name sortKey="Pelagatti, P" uniqKey="Pelagatti P">P Pelagatti</name></author><author><name sortKey="Zani, F" uniqKey="Zani F">F Zani</name></author></analytic></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct><biblStruct></biblStruct></listBibl></div1></back></TEI></PMC></double></record>Pour manipuler ce document sous Unix (Dilib)
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