Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents
A new series of 2-arylquinoline-4-carboxylic acid hydrazide–hydrazones was synthesized using an appropriate synthetic route. All the target compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus as an example for Gram-positive bacteria, Escherichia coli as a...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2006-12, Vol.14 (24), p.8675-8682 |
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| creator | Metwally, Kamel A. Abdel-Aziz, Lobna M. Lashine, El-Sayed M. Husseiny, Mohamed I. Badawy, Rania H. |
| description | A new series of 2-arylquinoline-4-carboxylic acid hydrazide–hydrazones was synthesized using an appropriate synthetic route. All the target compounds were evaluated for their in vitro antimicrobial activity against
Staphylococcus aureus as an example for Gram-positive bacteria,
Escherichia coli as an example for Gram-negative bacteria, and
Candida albicans as a representative of fungi. The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. Among the compounds tested, compounds having nitro substituents at the arylidene moiety showed the most potent antifungal as well as antibacterial activities against
E. coli. Compound
23 displayed an antifungal activity comparable to that of nystatin. However, none of the compounds demonstrated any antibacterial activity against
S. aureus. Hydrophobicity of the target compounds correlated weakly with their antibacterial and antifungal activities. The most potent compounds namely,
7,
18,
19,
22, and
23 were assessed for hemolytic toxicity and found to be non-hemolytic up to a concentration of 100
μg/mL. In addition, the most potent compound (
23) was evaluated for in vitro cytotoxic activity against various cancer cell lines. This compound was found to display no cytotoxic activity but rather it induces the proliferation rate of Hep-G2 cells. |
| doi_str_mv | 10.1016/j.bmc.2006.08.022 |
| format | Article |
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Staphylococcus aureus as an example for Gram-positive bacteria,
Escherichia coli as an example for Gram-negative bacteria, and
Candida albicans as a representative of fungi. The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. Among the compounds tested, compounds having nitro substituents at the arylidene moiety showed the most potent antifungal as well as antibacterial activities against
E. coli. Compound
23 displayed an antifungal activity comparable to that of nystatin. However, none of the compounds demonstrated any antibacterial activity against
S. aureus. Hydrophobicity of the target compounds correlated weakly with their antibacterial and antifungal activities. The most potent compounds namely,
7,
18,
19,
22, and
23 were assessed for hemolytic toxicity and found to be non-hemolytic up to a concentration of 100
μg/mL. In addition, the most potent compound (
23) was evaluated for in vitro cytotoxic activity against various cancer cell lines. This compound was found to display no cytotoxic activity but rather it induces the proliferation rate of Hep-G2 cells.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2006.08.022</identifier><identifier>PMID: 16949294</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>2-Arylquinoline-4-carboxylic acids ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antifungal agents ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Antimicrobial activity ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Breast Neoplasms - drug therapy ; Candida albicans ; Candida albicans - drug effects ; Carboxylic Acids - chemical synthesis ; Carboxylic Acids - chemistry ; Carboxylic Acids - pharmacology ; Carcinoma, Hepatocellular - drug therapy ; Cell Proliferation - drug effects ; Escherichia coli ; Escherichia coli - drug effects ; Hemolysis - drug effects ; Humans ; Hydrazones ; Hydrazones - chemical synthesis ; Hydrazones - chemistry ; Hydrazones - pharmacology ; Liver Neoplasms - drug therapy ; Medical sciences ; Microbial Sensitivity Tests ; Molecular Structure ; Pfitzinger reaction ; Pharmacology. Drug treatments ; Quinolones - chemical synthesis ; Quinolones - chemistry ; Quinolones - pharmacology ; Staphylococcus aureus ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship ; Tumor Cells, Cultured</subject><ispartof>Bioorganic & medicinal chemistry, 2006-12, Vol.14 (24), p.8675-8682</ispartof><rights>2006 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c412t-708a092c275c8ba62b818b8f100e246c9f569bbc6b26984182a70a1212d87c553</citedby><cites>FETCH-LOGICAL-c412t-708a092c275c8ba62b818b8f100e246c9f569bbc6b26984182a70a1212d87c553</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0968089606006833$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18272631$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16949294$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Metwally, Kamel A.</creatorcontrib><creatorcontrib>Abdel-Aziz, Lobna M.</creatorcontrib><creatorcontrib>Lashine, El-Sayed M.</creatorcontrib><creatorcontrib>Husseiny, Mohamed I.</creatorcontrib><creatorcontrib>Badawy, Rania H.</creatorcontrib><title>Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A new series of 2-arylquinoline-4-carboxylic acid hydrazide–hydrazones was synthesized using an appropriate synthetic route. All the target compounds were evaluated for their in vitro antimicrobial activity against
Staphylococcus aureus as an example for Gram-positive bacteria,
Escherichia coli as an example for Gram-negative bacteria, and
Candida albicans as a representative of fungi. The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. Among the compounds tested, compounds having nitro substituents at the arylidene moiety showed the most potent antifungal as well as antibacterial activities against
E. coli. Compound
23 displayed an antifungal activity comparable to that of nystatin. However, none of the compounds demonstrated any antibacterial activity against
S. aureus. Hydrophobicity of the target compounds correlated weakly with their antibacterial and antifungal activities. The most potent compounds namely,
7,
18,
19,
22, and
23 were assessed for hemolytic toxicity and found to be non-hemolytic up to a concentration of 100
μg/mL. In addition, the most potent compound (
23) was evaluated for in vitro cytotoxic activity against various cancer cell lines. This compound was found to display no cytotoxic activity but rather it induces the proliferation rate of Hep-G2 cells.</description><subject>2-Arylquinoline-4-carboxylic acids</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antimicrobial activity</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Breast Neoplasms - drug therapy</subject><subject>Candida albicans</subject><subject>Candida albicans - drug effects</subject><subject>Carboxylic Acids - chemical synthesis</subject><subject>Carboxylic Acids - chemistry</subject><subject>Carboxylic Acids - pharmacology</subject><subject>Carcinoma, Hepatocellular - drug therapy</subject><subject>Cell Proliferation - drug effects</subject><subject>Escherichia coli</subject><subject>Escherichia coli - drug effects</subject><subject>Hemolysis - drug effects</subject><subject>Humans</subject><subject>Hydrazones</subject><subject>Hydrazones - chemical synthesis</subject><subject>Hydrazones - chemistry</subject><subject>Hydrazones - pharmacology</subject><subject>Liver Neoplasms - drug therapy</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Pfitzinger reaction</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinolones - chemical synthesis</subject><subject>Quinolones - chemistry</subject><subject>Quinolones - pharmacology</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><subject>Tumor Cells, Cultured</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFu1DAQhi0EokvhAbggX-CWYDtZx4ZTVQFFqtRDy9kaOxPqleNs7aQiPH297Eq9cZrDfP-vmY-Q95zVnHH5eVfb0dWCMVkzVTMhXpANb2VbNY3mL8mGaakqprQ8I29y3jHGRKv5a3LGpW610O2GrFdrn-DvFDHTaaCigrSG6mHxcQo-YtVWDpKd_qzBOwrO9_T-X8D3mL_Q2zXO95h9phB7uk8Y_OhjqaD4CGGB2U-RwmE7l4VLk_UQKPzGOOe35NUAIeO70zwnv75_u7u8qq5vfvy8vLiuXMvFXHVMAdPCiW7rlAUprOLKqoEzhqKVTg9bqa110gqpVcuVgI4BF1z0qnPbbXNOPh1792l6WDDPZvTZYQgQcVqy4brrOtaoAvIjWO7MOeFg9smP5RnDmTn4NjtTfJuDb8OUKb5L5sOpfLEj9s-Jk-ACfDwBkB2EIUF0Pj9zSnRCNrxwX48cFhWPHpPJzmN02PuEbjb95P9zxhNwc562</recordid><startdate>20061215</startdate><enddate>20061215</enddate><creator>Metwally, Kamel A.</creator><creator>Abdel-Aziz, Lobna M.</creator><creator>Lashine, El-Sayed M.</creator><creator>Husseiny, Mohamed I.</creator><creator>Badawy, Rania H.</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>M7N</scope><scope>P64</scope></search><sort><creationdate>20061215</creationdate><title>Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents</title><author>Metwally, Kamel A. ; Abdel-Aziz, Lobna M. ; Lashine, El-Sayed M. ; Husseiny, Mohamed I. ; Badawy, Rania H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c412t-708a092c275c8ba62b818b8f100e246c9f569bbc6b26984182a70a1212d87c553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>2-Arylquinoline-4-carboxylic acids</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antifungal agents</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antimicrobial activity</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Breast Neoplasms - drug therapy</topic><topic>Candida albicans</topic><topic>Candida albicans - drug effects</topic><topic>Carboxylic Acids - chemical synthesis</topic><topic>Carboxylic Acids - chemistry</topic><topic>Carboxylic Acids - pharmacology</topic><topic>Carcinoma, Hepatocellular - drug therapy</topic><topic>Cell Proliferation - drug effects</topic><topic>Escherichia coli</topic><topic>Escherichia coli - drug effects</topic><topic>Hemolysis - drug effects</topic><topic>Humans</topic><topic>Hydrazones</topic><topic>Hydrazones - chemical synthesis</topic><topic>Hydrazones - chemistry</topic><topic>Hydrazones - pharmacology</topic><topic>Liver Neoplasms - drug therapy</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Pfitzinger reaction</topic><topic>Pharmacology. Drug treatments</topic><topic>Quinolones - chemical synthesis</topic><topic>Quinolones - chemistry</topic><topic>Quinolones - pharmacology</topic><topic>Staphylococcus aureus</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Structure-Activity Relationship</topic><topic>Tumor Cells, Cultured</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Metwally, Kamel A.</creatorcontrib><creatorcontrib>Abdel-Aziz, Lobna M.</creatorcontrib><creatorcontrib>Lashine, El-Sayed M.</creatorcontrib><creatorcontrib>Husseiny, Mohamed I.</creatorcontrib><creatorcontrib>Badawy, Rania H.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Metwally, Kamel A.</au><au>Abdel-Aziz, Lobna M.</au><au>Lashine, El-Sayed M.</au><au>Husseiny, Mohamed I.</au><au>Badawy, Rania H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2006-12-15</date><risdate>2006</risdate><volume>14</volume><issue>24</issue><spage>8675</spage><epage>8682</epage><pages>8675-8682</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A new series of 2-arylquinoline-4-carboxylic acid hydrazide–hydrazones was synthesized using an appropriate synthetic route. All the target compounds were evaluated for their in vitro antimicrobial activity against
Staphylococcus aureus as an example for Gram-positive bacteria,
Escherichia coli as an example for Gram-negative bacteria, and
Candida albicans as a representative of fungi. The minimum inhibitory concentration (MIC) was determined for test compounds as well as for reference standards. Among the compounds tested, compounds having nitro substituents at the arylidene moiety showed the most potent antifungal as well as antibacterial activities against
E. coli. Compound
23 displayed an antifungal activity comparable to that of nystatin. However, none of the compounds demonstrated any antibacterial activity against
S. aureus. Hydrophobicity of the target compounds correlated weakly with their antibacterial and antifungal activities. The most potent compounds namely,
7,
18,
19,
22, and
23 were assessed for hemolytic toxicity and found to be non-hemolytic up to a concentration of 100
μg/mL. In addition, the most potent compound (
23) was evaluated for in vitro cytotoxic activity against various cancer cell lines. This compound was found to display no cytotoxic activity but rather it induces the proliferation rate of Hep-G2 cells.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16949294</pmid><doi>10.1016/j.bmc.2006.08.022</doi><tpages>8</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0968-0896 |
| ispartof | Bioorganic & medicinal chemistry, 2006-12, Vol.14 (24), p.8675-8682 |
| issn | 0968-0896 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | 2-Arylquinoline-4-carboxylic acids Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal agents Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antimicrobial activity Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Breast Neoplasms - drug therapy Candida albicans Candida albicans - drug effects Carboxylic Acids - chemical synthesis Carboxylic Acids - chemistry Carboxylic Acids - pharmacology Carcinoma, Hepatocellular - drug therapy Cell Proliferation - drug effects Escherichia coli Escherichia coli - drug effects Hemolysis - drug effects Humans Hydrazones Hydrazones - chemical synthesis Hydrazones - chemistry Hydrazones - pharmacology Liver Neoplasms - drug therapy Medical sciences Microbial Sensitivity Tests Molecular Structure Pfitzinger reaction Pharmacology. Drug treatments Quinolones - chemical synthesis Quinolones - chemistry Quinolones - pharmacology Staphylococcus aureus Staphylococcus aureus - drug effects Structure-Activity Relationship Tumor Cells, Cultured |
| title | Hydrazones of 2-aryl-quinoline-4-carboxylic acid hydrazides: Synthesis and preliminary evaluation as antimicrobial agents |
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