Synthesis and Evaluation of Some New Isoquine Analogues for Antimalarial Activity
Amodiaquine is a 4-aminoquinoline antimalarial that can cause adverse side effects including hepatic and haematological toxicity. The drug toxicity involves the formation of an electrophilic metabolite, amodiaquine quinoneimine (AQQI), which binds to cellular macromolecules leading to hepatotoxicity...
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| Format: | Article |
| Language: | English |
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Wiley
2009-01-01
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| Series: | E-Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2009/693757 |
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| author | Chandra Nath Saha Sanjib Bhattacharya Dipak Chetia |
| author_facet | Chandra Nath Saha Sanjib Bhattacharya Dipak Chetia |
| author_sort | Chandra Nath Saha |
| collection | DOAJ |
| description | Amodiaquine is a 4-aminoquinoline antimalarial that can cause adverse side effects including hepatic and haematological toxicity. The drug toxicity involves the formation of an electrophilic metabolite, amodiaquine quinoneimine (AQQI), which binds to cellular macromolecules leading to hepatotoxicity and agranulocytosis. Interchange of the 3ʼ hydroxyl and the 4ʼ Mannich side-chain function of amodiaquine provides an amodiaquine regioisomer (isoquine) that cannot form toxic quinoneimine metabolites. By a simple two-step procedure, four isoquine analogues were synthesized and subsequently evaluated against the chloroquine sensitive RKL-2 strain of Plasmodium falciparum in vitro. All synthesized analogues demonstrated differential level of antimalarial activity against the test strain. However, no compound was found to exhibit better antimalarial property as compared to chloroquine. |
| format | Article |
| id | doaj-art-ed25d16ec2be443d9c94b219cce021f7 |
| institution | Kabale University |
| issn | 0973-4945 2090-9810 |
| language | English |
| publishDate | 2009-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | E-Journal of Chemistry |
| spelling | doaj-art-ed25d16ec2be443d9c94b219cce021f72025-02-03T06:11:48ZengWileyE-Journal of Chemistry0973-49452090-98102009-01-016S1S381S38910.1155/2009/693757Synthesis and Evaluation of Some New Isoquine Analogues for Antimalarial ActivityChandra Nath Saha0Sanjib Bhattacharya1Dipak Chetia2Department of Pharmaceutical Sciences, Dibrugarh University, Dibrugarh 786004, Assam, IndiaBengal School of Technology, Delhi Road, Sugandha, Hooghly 712102, West Bengal, IndiaDepartment of Pharmaceutical Sciences, Dibrugarh University, Dibrugarh 786004, Assam, IndiaAmodiaquine is a 4-aminoquinoline antimalarial that can cause adverse side effects including hepatic and haematological toxicity. The drug toxicity involves the formation of an electrophilic metabolite, amodiaquine quinoneimine (AQQI), which binds to cellular macromolecules leading to hepatotoxicity and agranulocytosis. Interchange of the 3ʼ hydroxyl and the 4ʼ Mannich side-chain function of amodiaquine provides an amodiaquine regioisomer (isoquine) that cannot form toxic quinoneimine metabolites. By a simple two-step procedure, four isoquine analogues were synthesized and subsequently evaluated against the chloroquine sensitive RKL-2 strain of Plasmodium falciparum in vitro. All synthesized analogues demonstrated differential level of antimalarial activity against the test strain. However, no compound was found to exhibit better antimalarial property as compared to chloroquine.http://dx.doi.org/10.1155/2009/693757 |
| spellingShingle | Chandra Nath Saha Sanjib Bhattacharya Dipak Chetia Synthesis and Evaluation of Some New Isoquine Analogues for Antimalarial Activity E-Journal of Chemistry |
| title | Synthesis and Evaluation of Some New Isoquine Analogues for Antimalarial Activity |
| title_full | Synthesis and Evaluation of Some New Isoquine Analogues for Antimalarial Activity |
| title_fullStr | Synthesis and Evaluation of Some New Isoquine Analogues for Antimalarial Activity |
| title_full_unstemmed | Synthesis and Evaluation of Some New Isoquine Analogues for Antimalarial Activity |
| title_short | Synthesis and Evaluation of Some New Isoquine Analogues for Antimalarial Activity |
| title_sort | synthesis and evaluation of some new isoquine analogues for antimalarial activity |
| url | http://dx.doi.org/10.1155/2009/693757 |
| work_keys_str_mv | AT chandranathsaha synthesisandevaluationofsomenewisoquineanaloguesforantimalarialactivity AT sanjibbhattacharya synthesisandevaluationofsomenewisoquineanaloguesforantimalarialactivity AT dipakchetia synthesisandevaluationofsomenewisoquineanaloguesforantimalarialactivity |