Synthesis and Antileishmanial activity of Piperoyl-Amino Acid Conjugates
Based on reported antileishmanial activity of naturally occurring alkaloid piperine and amino acid esters, their conjugates were synthesized by the hydrolysis of piperine to piperic acid followed by reaction with amino acid methyl esters. These conjugates were further converted to compounds with fre...
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| Veröffentlicht in: | European journal of medicinal chemistry 2010-08, Vol.45 (8), p.3439-3445 |
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| container_title | European journal of medicinal chemistry |
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| creator | Singh, Inder Pal Jain, Shreyans Kumar Kaur, Amandeep Singh, Sukhvinder Kumar, Rajender Garg, Prabha Sharma, Shyam Sundar Arora, Sunil Kumar |
| description | Based on reported antileishmanial activity of naturally occurring alkaloid piperine and amino acid esters, their conjugates were synthesized by the hydrolysis of piperine to piperic acid followed by reaction with amino acid methyl esters. These conjugates were further converted to compounds with free carboxyl group and those with reduced double bonds. The synthesized compounds were evaluated for activity against promastigote and amastigote forms of
L.
donovani in vitro. All the compounds showed better activity than either piperine or the amino acid methyl esters. Piperoyl-valine methyl ester was the most active compound showing an IC
50 of 0.075
mM against the amastigotes. Two active compounds were evaluated for
in vivo activity in golden hamster model of leishmaniasis.
[Display omitted] |
| doi_str_mv | 10.1016/j.ejmech.2010.04.033 |
| format | Article |
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L.
donovani in vitro. All the compounds showed better activity than either piperine or the amino acid methyl esters. Piperoyl-valine methyl ester was the most active compound showing an IC
50 of 0.075
mM against the amastigotes. Two active compounds were evaluated for
in vivo activity in golden hamster model of leishmaniasis.
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L.
donovani in vitro. All the compounds showed better activity than either piperine or the amino acid methyl esters. Piperoyl-valine methyl ester was the most active compound showing an IC
50 of 0.075
mM against the amastigotes. Two active compounds were evaluated for
in vivo activity in golden hamster model of leishmaniasis.
[Display omitted]</description><subject>Alkaloids - chemistry</subject><subject>Amastigote</subject><subject>Amino acid</subject><subject>Amino Acids - chemical synthesis</subject><subject>Amino Acids - chemistry</subject><subject>Amino Acids - pharmacology</subject><subject>Amino Acids - toxicity</subject><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiparasitic agents</subject><subject>Antiprotozoal Agents - chemical synthesis</subject><subject>Antiprotozoal Agents - chemistry</subject><subject>Antiprotozoal Agents - pharmacology</subject><subject>Antiprotozoal Agents - therapeutic use</subject><subject>Benzodioxoles - chemistry</subject><subject>Biological and medical sciences</subject><subject>Catalytic Domain</subject><subject>Cricetinae</subject><subject>Esters - chemistry</subject><subject>Humans</subject><subject>Inhibitory Concentration 50</subject><subject>Leishmania donovani - drug effects</subject><subject>Leishmaniasis</subject><subject>Leishmaniasis - drug therapy</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>Piperidines - chemistry</subject><subject>Piperine</subject><subject>Polyunsaturated Alkamides - chemistry</subject><subject>Promastigote</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1rGzEQhkVpSNw0_yCEvZSe1hl97UqXgjFpXQg0kPQsZGm21rKrdaR1wP8-a-ykt5wGhud9Z3gIuaYwp0Cr23aObY9uM2cwrUDMgfNPZEbrSpWcSfGZzIAxXkrGxQX5knMLALICOCcXDKSotKIzsnrcx3GDOeTCRl8s4hg6DHnT2xhsV1g3hpcw7ouhKR7CFtOw78pFH-JQLFzwxXKI7e6fHTF_JWeN7TJeneYl-fvz7mm5Ku___Pq9XNyXTsh6LCuOWlOJNa3kuvHoa-5BUYGOuRoqqZmXWqMX60ZCo7SumzVzTlml6gos45fk-7F3m4bnHebR9CE77DobcdhlU3POJZNUTaQ4ki4NOSdszDaF3qa9oWAOCk1rjgrNQaEBYSaFU-zmdGC37tG_h96cTcC3E2Czs12TbHQh_-eYVkIzOXE_jhxOOl4CJpNdwOjQh4RuNH4IH3_yClezkIg</recordid><startdate>20100801</startdate><enddate>20100801</enddate><creator>Singh, Inder Pal</creator><creator>Jain, Shreyans Kumar</creator><creator>Kaur, Amandeep</creator><creator>Singh, Sukhvinder</creator><creator>Kumar, Rajender</creator><creator>Garg, Prabha</creator><creator>Sharma, Shyam Sundar</creator><creator>Arora, Sunil Kumar</creator><general>Elsevier Masson SAS</general><general>Elsevier</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>7X8</scope></search><sort><creationdate>20100801</creationdate><title>Synthesis and Antileishmanial activity of Piperoyl-Amino Acid Conjugates</title><author>Singh, Inder Pal ; Jain, Shreyans Kumar ; Kaur, Amandeep ; Singh, Sukhvinder ; Kumar, Rajender ; Garg, Prabha ; Sharma, Shyam Sundar ; Arora, Sunil Kumar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c457t-63e9915e7165bfded73d0814ec2c706592d599ed4bf50f8997fb2cc8a88760a23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkaloids - chemistry</topic><topic>Amastigote</topic><topic>Amino acid</topic><topic>Amino Acids - chemical synthesis</topic><topic>Amino Acids - chemistry</topic><topic>Amino Acids - pharmacology</topic><topic>Amino Acids - toxicity</topic><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiparasitic agents</topic><topic>Antiprotozoal Agents - chemical synthesis</topic><topic>Antiprotozoal Agents - chemistry</topic><topic>Antiprotozoal Agents - pharmacology</topic><topic>Antiprotozoal Agents - therapeutic use</topic><topic>Benzodioxoles - chemistry</topic><topic>Biological and medical sciences</topic><topic>Catalytic Domain</topic><topic>Cricetinae</topic><topic>Esters - chemistry</topic><topic>Humans</topic><topic>Inhibitory Concentration 50</topic><topic>Leishmania donovani - drug effects</topic><topic>Leishmaniasis</topic><topic>Leishmaniasis - drug therapy</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>Piperidines - chemistry</topic><topic>Piperine</topic><topic>Polyunsaturated Alkamides - chemistry</topic><topic>Promastigote</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Singh, Inder Pal</creatorcontrib><creatorcontrib>Jain, Shreyans Kumar</creatorcontrib><creatorcontrib>Kaur, Amandeep</creatorcontrib><creatorcontrib>Singh, Sukhvinder</creatorcontrib><creatorcontrib>Kumar, Rajender</creatorcontrib><creatorcontrib>Garg, Prabha</creatorcontrib><creatorcontrib>Sharma, Shyam Sundar</creatorcontrib><creatorcontrib>Arora, Sunil Kumar</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>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Singh, Inder Pal</au><au>Jain, Shreyans Kumar</au><au>Kaur, Amandeep</au><au>Singh, Sukhvinder</au><au>Kumar, Rajender</au><au>Garg, Prabha</au><au>Sharma, Shyam Sundar</au><au>Arora, Sunil Kumar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Antileishmanial activity of Piperoyl-Amino Acid Conjugates</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2010-08-01</date><risdate>2010</risdate><volume>45</volume><issue>8</issue><spage>3439</spage><epage>3445</epage><pages>3439-3445</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Based on reported antileishmanial activity of naturally occurring alkaloid piperine and amino acid esters, their conjugates were synthesized by the hydrolysis of piperine to piperic acid followed by reaction with amino acid methyl esters. These conjugates were further converted to compounds with free carboxyl group and those with reduced double bonds. The synthesized compounds were evaluated for activity against promastigote and amastigote forms of
L.
donovani in vitro. All the compounds showed better activity than either piperine or the amino acid methyl esters. Piperoyl-valine methyl ester was the most active compound showing an IC
50 of 0.075
mM against the amastigotes. Two active compounds were evaluated for
in vivo activity in golden hamster model of leishmaniasis.
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Alkaloids - chemistry Amastigote Amino acid Amino Acids - chemical synthesis Amino Acids - chemistry Amino Acids - pharmacology Amino Acids - toxicity Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antiparasitic agents Antiprotozoal Agents - chemical synthesis Antiprotozoal Agents - chemistry Antiprotozoal Agents - pharmacology Antiprotozoal Agents - therapeutic use Benzodioxoles - chemistry Biological and medical sciences Catalytic Domain Cricetinae Esters - chemistry Humans Inhibitory Concentration 50 Leishmania donovani - drug effects Leishmaniasis Leishmaniasis - drug therapy Male Medical sciences Models, Molecular Pharmacology. Drug treatments Piperidines - chemistry Piperine Polyunsaturated Alkamides - chemistry Promastigote |
| title | Synthesis and Antileishmanial activity of Piperoyl-Amino Acid Conjugates |
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