Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles
Some novel α and β ionone based chalcones and their dihydropyrazolidines/pyrazolidines have been synthesized and evaluated for their in vitro and in vivo antileishmanial activities against Leishmania donovani. Amongest all, one compound (4d) exhibited significant in vitro activity against intracellu...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2013-01, Vol.23 (1), p.248-251 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Tiwari, Avinash Kumar, Santosh Suryawanshi, S.N. Mittal, Monika Vishwakarma, Preeti Gupta, Suman |
| description | Some novel α and β ionone based chalcones and their dihydropyrazolidines/pyrazolidines have been synthesized and evaluated for their in vitro and in vivo antileishmanial activities against Leishmania donovani. Amongest all, one compound (4d) exhibited significant in vitro activity against intracellular amastigotes of Leishmania donovani with IC50 values of 7.49μM and was found promising as compared to reference drug, miltefosine. On the basis of good Selectivity Index (S.I.), the compound was further tested for its in vivo response against Leishmania donovani/hamster model and has shown significant inhibition of parasite multiplication (81%). The present study has helped us in identifying a new lead that could be exploited as a potential antileishmanial agent. |
| doi_str_mv | 10.1016/j.bmcl.2012.10.110 |
| format | Article |
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Amongest all, one compound (4d) exhibited significant in vitro activity against intracellular amastigotes of Leishmania donovani with IC50 values of 7.49μM and was found promising as compared to reference drug, miltefosine. On the basis of good Selectivity Index (S.I.), the compound was further tested for its in vivo response against Leishmania donovani/hamster model and has shown significant inhibition of parasite multiplication (81%). The present study has helped us in identifying a new lead that could be exploited as a potential antileishmanial agent.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2012.10.110</identifier><identifier>PMID: 23177254</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>amastigotes ; animal models ; Animals ; Antiprotozoal Agents - chemical synthesis ; Antiprotozoal Agents - therapeutic use ; Antiprotozoal Agents - toxicity ; Cell Line, Tumor ; Cell Survival - drug effects ; Chalcones ; Chalcones - chemistry ; Chalcones - therapeutic use ; Chalcones - toxicity ; chemistry ; chemotherapy ; Cricetinae ; Disease Models, Animal ; Drug Evaluation, Preclinical ; drugs ; Hamster ; Heterocyclic Compounds - chemistry ; Heterocyclic Compounds - therapeutic use ; Heterocyclic Compounds - toxicity ; Humans ; In vitro testing ; In vivo trial ; inhibitory concentration 50 ; Leishmania donovani ; leishmaniasis ; Leishmaniasis - drug therapy ; Leishmaniasis, Visceral - drug therapy ; parasites ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - therapeutic use ; Pyrazoles - toxicity ; Pyrazolidines ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry letters, 2013-01, Vol.23 (1), p.248-251</ispartof><rights>2012 Elsevier Ltd</rights><rights>Copyright © 2012 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c380t-daa178eb3263ed1c14ce6a7705f3c2f0b0085682c96096f1bd8012c6002908b13</citedby><cites>FETCH-LOGICAL-c380t-daa178eb3263ed1c14ce6a7705f3c2f0b0085682c96096f1bd8012c6002908b13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2012.10.110$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,4024,27923,27924,27925,45995</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23177254$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tiwari, Avinash</creatorcontrib><creatorcontrib>Kumar, Santosh</creatorcontrib><creatorcontrib>Suryawanshi, S.N.</creatorcontrib><creatorcontrib>Mittal, Monika</creatorcontrib><creatorcontrib>Vishwakarma, Preeti</creatorcontrib><creatorcontrib>Gupta, Suman</creatorcontrib><title>Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Some novel α and β ionone based chalcones and their dihydropyrazolidines/pyrazolidines have been synthesized and evaluated for their in vitro and in vivo antileishmanial activities against Leishmania donovani. Amongest all, one compound (4d) exhibited significant in vitro activity against intracellular amastigotes of Leishmania donovani with IC50 values of 7.49μM and was found promising as compared to reference drug, miltefosine. On the basis of good Selectivity Index (S.I.), the compound was further tested for its in vivo response against Leishmania donovani/hamster model and has shown significant inhibition of parasite multiplication (81%). The present study has helped us in identifying a new lead that could be exploited as a potential antileishmanial agent.</description><subject>amastigotes</subject><subject>animal models</subject><subject>Animals</subject><subject>Antiprotozoal Agents - chemical synthesis</subject><subject>Antiprotozoal Agents - therapeutic use</subject><subject>Antiprotozoal Agents - toxicity</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>Chalcones</subject><subject>Chalcones - chemistry</subject><subject>Chalcones - therapeutic use</subject><subject>Chalcones - toxicity</subject><subject>chemistry</subject><subject>chemotherapy</subject><subject>Cricetinae</subject><subject>Disease Models, Animal</subject><subject>Drug Evaluation, Preclinical</subject><subject>drugs</subject><subject>Hamster</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Heterocyclic Compounds - therapeutic use</subject><subject>Heterocyclic Compounds - toxicity</subject><subject>Humans</subject><subject>In vitro testing</subject><subject>In vivo trial</subject><subject>inhibitory concentration 50</subject><subject>Leishmania donovani</subject><subject>leishmaniasis</subject><subject>Leishmaniasis - drug therapy</subject><subject>Leishmaniasis, Visceral - drug therapy</subject><subject>parasites</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - therapeutic use</subject><subject>Pyrazoles - toxicity</subject><subject>Pyrazolidines</subject><subject>Structure-Activity Relationship</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE1v1DAQhi0EokvhD3CAHLlkmXGcxEFc0IqPSpV6KJV6M44zYb1y4mBnV8q_r8MWjj15NHreV56HsbcIWwSsPh627WDclgPy7bpDeMY2KCqRFwLK52wDTQW5bMT9BXsV4wEABQjxkl3wAuual2LDfu32NPh5T0FPS-b7zJGN-0GPVkcbs0mHObv_lN0uY2LWjR67rLWeTtod9Wz9uIZGfyKXzRQmGheX7SmN3izGUXzNXvTaRXrz-F6yu29ff-5-5Nc33692X65zU0iY805rrCW1Ba8K6tCgMFTpuoayLwzvoQWQZSW5SSc1VY9tJ9PZpgLgDcgWi0v24dw7Bf_nSHFWg42GnNMj-WNUyAXIpimQJ5SfURN8jIF6NQU76LAoBLWaVQe1mlWr2b87hBR699h_bAfq_kf-qUzA-zPQa6_072CjurtNDWXSXqCQdSI-nwlKHk6WgorG0mios4HMrDpvn_rBA4usk6Y</recordid><startdate>20130101</startdate><enddate>20130101</enddate><creator>Tiwari, Avinash</creator><creator>Kumar, Santosh</creator><creator>Suryawanshi, S.N.</creator><creator>Mittal, Monika</creator><creator>Vishwakarma, Preeti</creator><creator>Gupta, Suman</creator><general>Elsevier Ltd</general><scope>FBQ</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>20130101</creationdate><title>Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles</title><author>Tiwari, Avinash ; Kumar, Santosh ; Suryawanshi, S.N. ; Mittal, Monika ; Vishwakarma, Preeti ; Gupta, Suman</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c380t-daa178eb3263ed1c14ce6a7705f3c2f0b0085682c96096f1bd8012c6002908b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>amastigotes</topic><topic>animal models</topic><topic>Animals</topic><topic>Antiprotozoal Agents - chemical synthesis</topic><topic>Antiprotozoal Agents - therapeutic use</topic><topic>Antiprotozoal Agents - toxicity</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>Chalcones</topic><topic>Chalcones - chemistry</topic><topic>Chalcones - therapeutic use</topic><topic>Chalcones - toxicity</topic><topic>chemistry</topic><topic>chemotherapy</topic><topic>Cricetinae</topic><topic>Disease Models, Animal</topic><topic>Drug Evaluation, Preclinical</topic><topic>drugs</topic><topic>Hamster</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Heterocyclic Compounds - therapeutic use</topic><topic>Heterocyclic Compounds - toxicity</topic><topic>Humans</topic><topic>In vitro testing</topic><topic>In vivo trial</topic><topic>inhibitory concentration 50</topic><topic>Leishmania donovani</topic><topic>leishmaniasis</topic><topic>Leishmaniasis - drug therapy</topic><topic>Leishmaniasis, Visceral - drug therapy</topic><topic>parasites</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - therapeutic use</topic><topic>Pyrazoles - toxicity</topic><topic>Pyrazolidines</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tiwari, Avinash</creatorcontrib><creatorcontrib>Kumar, Santosh</creatorcontrib><creatorcontrib>Suryawanshi, S.N.</creatorcontrib><creatorcontrib>Mittal, Monika</creatorcontrib><creatorcontrib>Vishwakarma, Preeti</creatorcontrib><creatorcontrib>Gupta, Suman</creatorcontrib><collection>AGRIS</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>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tiwari, Avinash</au><au>Kumar, Santosh</au><au>Suryawanshi, S.N.</au><au>Mittal, Monika</au><au>Vishwakarma, Preeti</au><au>Gupta, Suman</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2013-01-01</date><risdate>2013</risdate><volume>23</volume><issue>1</issue><spage>248</spage><epage>251</epage><pages>248-251</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Some novel α and β ionone based chalcones and their dihydropyrazolidines/pyrazolidines have been synthesized and evaluated for their in vitro and in vivo antileishmanial activities against Leishmania donovani. Amongest all, one compound (4d) exhibited significant in vitro activity against intracellular amastigotes of Leishmania donovani with IC50 values of 7.49μM and was found promising as compared to reference drug, miltefosine. On the basis of good Selectivity Index (S.I.), the compound was further tested for its in vivo response against Leishmania donovani/hamster model and has shown significant inhibition of parasite multiplication (81%). The present study has helped us in identifying a new lead that could be exploited as a potential antileishmanial agent.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>23177254</pmid><doi>10.1016/j.bmcl.2012.10.110</doi><tpages>4</tpages></addata></record> |
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| subjects | amastigotes animal models Animals Antiprotozoal Agents - chemical synthesis Antiprotozoal Agents - therapeutic use Antiprotozoal Agents - toxicity Cell Line, Tumor Cell Survival - drug effects Chalcones Chalcones - chemistry Chalcones - therapeutic use Chalcones - toxicity chemistry chemotherapy Cricetinae Disease Models, Animal Drug Evaluation, Preclinical drugs Hamster Heterocyclic Compounds - chemistry Heterocyclic Compounds - therapeutic use Heterocyclic Compounds - toxicity Humans In vitro testing In vivo trial inhibitory concentration 50 Leishmania donovani leishmaniasis Leishmaniasis - drug therapy Leishmaniasis, Visceral - drug therapy parasites Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - therapeutic use Pyrazoles - toxicity Pyrazolidines Structure-Activity Relationship |
| title | Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles |
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