Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents
Some chalcones have been designed and synthesized using Claisen-Schmidt reactions as inhibitors of the ferredoxin and ferredoxin-NADP+ reductase interaction to pursue a new selective antimalaria agent. The synthesized compounds exhibited inhibition interactions between PfFd-PfFNR in the range of 10....
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MDPI AG
2014-12-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/19/12/21473 |
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| author | Hery Suwito Jumina Mustofa Pratiwi Pudjiastuti Much Zaenal Fanani Yoko Kimata-Ariga Ritsuko Katahira Toru Kawakami Toshimichi Fujiwara Toshiharu Hase Hasnah Mohd Sirat Ni Nyoman Tri Puspaningsih |
| author_facet | Hery Suwito Jumina Mustofa Pratiwi Pudjiastuti Much Zaenal Fanani Yoko Kimata-Ariga Ritsuko Katahira Toru Kawakami Toshimichi Fujiwara Toshiharu Hase Hasnah Mohd Sirat Ni Nyoman Tri Puspaningsih |
| author_sort | Hery Suwito |
| collection | DOAJ |
| description | Some chalcones have been designed and synthesized using Claisen-Schmidt reactions as inhibitors of the ferredoxin and ferredoxin-NADP+ reductase interaction to pursue a new selective antimalaria agent. The synthesized compounds exhibited inhibition interactions between PfFd-PfFNR in the range of 10.94%–50%. The three strongest inhibition activities were shown by (E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (50%), (E)-1-(4-aminophenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one (38.16%), and (E)-1-(4-aminophenyl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one (31.58%). From the docking experiments we established that the amino group of the methoxyamino chlacone derivatives plays an important role in the inhibition activity by electrostatic interaction through salt bridges and that it forms more stable and better affinity complexes with FNR than with Fd. |
| first_indexed | 2024-12-11T18:07:35Z |
| format | Article |
| id | doaj.art-e2352b8a2a3d4d51b985bce9e41879eb |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T18:07:35Z |
| publishDate | 2014-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e2352b8a2a3d4d51b985bce9e41879eb2022-12-22T00:55:40ZengMDPI AGMolecules1420-30492014-12-011912214732148810.3390/molecules191221473molecules191221473Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial AgentsHery Suwito0Jumina1Mustofa2Pratiwi Pudjiastuti3Much Zaenal Fanani4Yoko Kimata-Ariga5Ritsuko Katahira6Toru Kawakami7Toshimichi Fujiwara8Toshiharu Hase9Hasnah Mohd Sirat10Ni Nyoman Tri Puspaningsih11Department of Chemistry, Faculty of Science and Mathematics, University of Gajah Mada, Jogjakarta 55281, IndonesiaDepartment of Chemistry, Faculty of Science and Mathematics, University of Gajah Mada, Jogjakarta 55281, IndonesiaDepartment of Pharmacology and Therapy, Faculty of Medicine, University of Gajah Mada, Jogjakarta 55281, IndonesiaDepartment of Chemistry, Faculty of Science and Technology, Airlangga University, Surabaya 60115, IndonesiaInstitute of Tropical Disease, Airlangga University, Surabaya 60115, IndonesiaInstitute of Protein Research, Osaka University, 3-2 Yamadoaka, Suita-Shi, Osaka 656-0871 JapanInstitute of Protein Research, Osaka University, 3-2 Yamadoaka, Suita-Shi, Osaka 656-0871 JapanInstitute of Protein Research, Osaka University, 3-2 Yamadoaka, Suita-Shi, Osaka 656-0871 JapanInstitute of Protein Research, Osaka University, 3-2 Yamadoaka, Suita-Shi, Osaka 656-0871 JapanInstitute of Protein Research, Osaka University, 3-2 Yamadoaka, Suita-Shi, Osaka 656-0871 JapanDepartment of Chemistry, Faculty of Science, University Technology Malaya, Johor Bahru 81310, MalaysiaDepartment of Chemistry, Faculty of Science and Technology, Airlangga University, Surabaya 60115, IndonesiaSome chalcones have been designed and synthesized using Claisen-Schmidt reactions as inhibitors of the ferredoxin and ferredoxin-NADP+ reductase interaction to pursue a new selective antimalaria agent. The synthesized compounds exhibited inhibition interactions between PfFd-PfFNR in the range of 10.94%–50%. The three strongest inhibition activities were shown by (E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (50%), (E)-1-(4-aminophenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one (38.16%), and (E)-1-(4-aminophenyl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one (31.58%). From the docking experiments we established that the amino group of the methoxyamino chlacone derivatives plays an important role in the inhibition activity by electrostatic interaction through salt bridges and that it forms more stable and better affinity complexes with FNR than with Fd.http://www.mdpi.com/1420-3049/19/12/21473methoxyamino chalconesantimalarialPfFd-PfFNR inhibitor |
| spellingShingle | Hery Suwito Jumina Mustofa Pratiwi Pudjiastuti Much Zaenal Fanani Yoko Kimata-Ariga Ritsuko Katahira Toru Kawakami Toshimichi Fujiwara Toshiharu Hase Hasnah Mohd Sirat Ni Nyoman Tri Puspaningsih Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents Molecules methoxyamino chalcones antimalarial PfFd-PfFNR inhibitor |
| title | Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents |
| title_full | Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents |
| title_fullStr | Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents |
| title_full_unstemmed | Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents |
| title_short | Design and Synthesis of Chalcone Derivatives as Inhibitors of the Ferredoxin — Ferredoxin-NADP+ Reductase Interaction of Plasmodium falciparum: Pursuing New Antimalarial Agents |
| title_sort | design and synthesis of chalcone derivatives as inhibitors of the ferredoxin ferredoxin nadp reductase interaction of plasmodium falciparum pursuing new antimalarial agents |
| topic | methoxyamino chalcones antimalarial PfFd-PfFNR inhibitor |
| url | http://www.mdpi.com/1420-3049/19/12/21473 |
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