Synthesis of Unsymmetrical Sulfides and Their Oxidation to Sulfones to Discover Potent Antileishmanial Agents
Unsymmetrical sulfides were first synthesized using combinations of a 1,3-dicarbonyl, an aromatic aldehyde and a thiol in the presence of 10 mol % ethanolic piperidine. These sulfides derivatives were subsequently converted into corresponding sulfones via oxidation in the presence of m-chloroperoxyb...
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| Veröffentlicht in: | ACS combinatorial science 2015-11, Vol.17 (11), p.671-681 |
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| creator | Dar, Ajaz A Enjamuri, Nagasuresh Shadab, Md Ali, Nahid Khan, Abu T |
| description | Unsymmetrical sulfides were first synthesized using combinations of a 1,3-dicarbonyl, an aromatic aldehyde and a thiol in the presence of 10 mol % ethanolic piperidine. These sulfides derivatives were subsequently converted into corresponding sulfones via oxidation in the presence of m-chloroperoxybenzoic acid (m-CPBA) at ice-bath to room temperature. The former reaction was achieved at room temperature through one-pot three-component. The later was obtained in good yields using mild reaction conditions with flexibility in choice from a range of substrates. The antimicrobial properties of the newly synthesized sulfone derivatives were investigated against the protozoan parasite, Leishmania donovani, a causative agent of visceral leishmaniasis (VL). Nine sulfone derivatives were found to be efficacious and exhibited significant antimicrobial activity. Further, these compounds were nontoxic on murine peritoneal macrophages thus eliminating potential cytoxicity in the host cells. These compounds may be indicated as potential leads in the treatment of visceral leishmaniasis. |
| doi_str_mv | 10.1021/acscombsci.5b00044 |
| format | Article |
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These sulfides derivatives were subsequently converted into corresponding sulfones via oxidation in the presence of m-chloroperoxybenzoic acid (m-CPBA) at ice-bath to room temperature. The former reaction was achieved at room temperature through one-pot three-component. The later was obtained in good yields using mild reaction conditions with flexibility in choice from a range of substrates. The antimicrobial properties of the newly synthesized sulfone derivatives were investigated against the protozoan parasite, Leishmania donovani, a causative agent of visceral leishmaniasis (VL). Nine sulfone derivatives were found to be efficacious and exhibited significant antimicrobial activity. Further, these compounds were nontoxic on murine peritoneal macrophages thus eliminating potential cytoxicity in the host cells. 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Sci</addtitle><description>Unsymmetrical sulfides were first synthesized using combinations of a 1,3-dicarbonyl, an aromatic aldehyde and a thiol in the presence of 10 mol % ethanolic piperidine. These sulfides derivatives were subsequently converted into corresponding sulfones via oxidation in the presence of m-chloroperoxybenzoic acid (m-CPBA) at ice-bath to room temperature. The former reaction was achieved at room temperature through one-pot three-component. The later was obtained in good yields using mild reaction conditions with flexibility in choice from a range of substrates. The antimicrobial properties of the newly synthesized sulfone derivatives were investigated against the protozoan parasite, Leishmania donovani, a causative agent of visceral leishmaniasis (VL). Nine sulfone derivatives were found to be efficacious and exhibited significant antimicrobial activity. Further, these compounds were nontoxic on murine peritoneal macrophages thus eliminating potential cytoxicity in the host cells. These compounds may be indicated as potential leads in the treatment of visceral leishmaniasis.</description><subject>Animals</subject><subject>Antiprotozoal Agents - chemical synthesis</subject><subject>Antiprotozoal Agents - chemistry</subject><subject>Antiprotozoal Agents - pharmacology</subject><subject>Cell Survival - drug effects</subject><subject>Cells, Cultured</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Cricetinae</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Discovery</subject><subject>Humans</subject><subject>Leishmania donovani - drug effects</subject><subject>Macrophages - drug effects</subject><subject>Macrophages - parasitology</subject><subject>Mice</subject><subject>Mice, Inbred BALB C</subject><subject>Models, Molecular</subject><subject>Molecular Structure</subject><subject>Oxidation-Reduction</subject><subject>Parasitic Sensitivity Tests</subject><subject>Structure-Activity Relationship</subject><subject>Sulfides - chemical synthesis</subject><subject>Sulfides - chemistry</subject><subject>Sulfides - pharmacology</subject><subject>Sulfones - chemical synthesis</subject><subject>Sulfones - chemistry</subject><subject>Sulfones - pharmacology</subject><issn>2156-8952</issn><issn>2156-8944</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9UMtOAyEUJUZjTe0PuDAs3bQCwzxYNr4TE01s1xOGuViaGVBgjP170da6c3Vv7nnk3IPQGSUzShi9lCoo1zdBmVneEEI4P0AnjObFtBKcH-73nI3QJIQ1-eEIVpBjNGIF5zQj2QnqXzY2riCYgJ3GSxs2fQ_RGyU7_DJ02rQQsLQtXqzAePz0aVoZjbM4uh_c2YSn_dqkOB_g8bOLYCOe22g6MGHVS2uS1_w1XcMpOtKyCzDZzTFa3t4sru6nj093D1fzx6nMOItTkLkQZVNqXTYV5xUpQNEcRKVk2RZCN4oKXioQrGkzqhNYtTkjZVVVULZaZGN0sfV98-59gBDrPuWDrpMW3BBqWmYsI6JIc4zYlqq8C8GDrt-86aXf1JTU303Xf03Xu6aT6HznPzQ9tHvJb6-JMNsSkrheu8Hb9O5_jl9yVI3j</recordid><startdate>20151109</startdate><enddate>20151109</enddate><creator>Dar, Ajaz A</creator><creator>Enjamuri, Nagasuresh</creator><creator>Shadab, Md</creator><creator>Ali, Nahid</creator><creator>Khan, Abu T</creator><general>American Chemical Society</general><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>7X8</scope></search><sort><creationdate>20151109</creationdate><title>Synthesis of Unsymmetrical Sulfides and Their Oxidation to Sulfones to Discover Potent Antileishmanial Agents</title><author>Dar, Ajaz A ; Enjamuri, Nagasuresh ; Shadab, Md ; Ali, Nahid ; Khan, Abu T</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a342t-ea5997b7ff7b844806ec15e98ca7d69fbc1947ce92bd31fec18d5207888e7df93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Animals</topic><topic>Antiprotozoal Agents - chemical synthesis</topic><topic>Antiprotozoal Agents - chemistry</topic><topic>Antiprotozoal Agents - pharmacology</topic><topic>Cell Survival - drug effects</topic><topic>Cells, Cultured</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Cricetinae</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Discovery</topic><topic>Humans</topic><topic>Leishmania donovani - drug effects</topic><topic>Macrophages - drug effects</topic><topic>Macrophages - parasitology</topic><topic>Mice</topic><topic>Mice, Inbred BALB C</topic><topic>Models, Molecular</topic><topic>Molecular Structure</topic><topic>Oxidation-Reduction</topic><topic>Parasitic Sensitivity Tests</topic><topic>Structure-Activity Relationship</topic><topic>Sulfides - chemical synthesis</topic><topic>Sulfides - chemistry</topic><topic>Sulfides - pharmacology</topic><topic>Sulfones - chemical synthesis</topic><topic>Sulfones - chemistry</topic><topic>Sulfones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dar, Ajaz A</creatorcontrib><creatorcontrib>Enjamuri, Nagasuresh</creatorcontrib><creatorcontrib>Shadab, Md</creatorcontrib><creatorcontrib>Ali, Nahid</creatorcontrib><creatorcontrib>Khan, Abu T</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>ACS combinatorial science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dar, Ajaz A</au><au>Enjamuri, Nagasuresh</au><au>Shadab, Md</au><au>Ali, Nahid</au><au>Khan, Abu T</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Unsymmetrical Sulfides and Their Oxidation to Sulfones to Discover Potent Antileishmanial Agents</atitle><jtitle>ACS combinatorial science</jtitle><addtitle>ACS Comb. Sci</addtitle><date>2015-11-09</date><risdate>2015</risdate><volume>17</volume><issue>11</issue><spage>671</spage><epage>681</epage><pages>671-681</pages><issn>2156-8952</issn><eissn>2156-8944</eissn><abstract>Unsymmetrical sulfides were first synthesized using combinations of a 1,3-dicarbonyl, an aromatic aldehyde and a thiol in the presence of 10 mol % ethanolic piperidine. These sulfides derivatives were subsequently converted into corresponding sulfones via oxidation in the presence of m-chloroperoxybenzoic acid (m-CPBA) at ice-bath to room temperature. The former reaction was achieved at room temperature through one-pot three-component. The later was obtained in good yields using mild reaction conditions with flexibility in choice from a range of substrates. The antimicrobial properties of the newly synthesized sulfone derivatives were investigated against the protozoan parasite, Leishmania donovani, a causative agent of visceral leishmaniasis (VL). Nine sulfone derivatives were found to be efficacious and exhibited significant antimicrobial activity. Further, these compounds were nontoxic on murine peritoneal macrophages thus eliminating potential cytoxicity in the host cells. These compounds may be indicated as potential leads in the treatment of visceral leishmaniasis.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>26441303</pmid><doi>10.1021/acscombsci.5b00044</doi><tpages>11</tpages></addata></record> |
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| subjects | Animals Antiprotozoal Agents - chemical synthesis Antiprotozoal Agents - chemistry Antiprotozoal Agents - pharmacology Cell Survival - drug effects Cells, Cultured Combinatorial Chemistry Techniques Cricetinae Dose-Response Relationship, Drug Drug Discovery Humans Leishmania donovani - drug effects Macrophages - drug effects Macrophages - parasitology Mice Mice, Inbred BALB C Models, Molecular Molecular Structure Oxidation-Reduction Parasitic Sensitivity Tests Structure-Activity Relationship Sulfides - chemical synthesis Sulfides - chemistry Sulfides - pharmacology Sulfones - chemical synthesis Sulfones - chemistry Sulfones - pharmacology |
| title | Synthesis of Unsymmetrical Sulfides and Their Oxidation to Sulfones to Discover Potent Antileishmanial Agents |
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