dc.contributor.author | Masila, VM | |
dc.contributor.author | Ndakala, AJ | |
dc.contributor.author | Byamukama, R | |
dc.contributor.author | Midiwo, JO | |
dc.contributor.author | Kamau, RW | |
dc.contributor.author | Wang, M | |
dc.contributor.author | Kumarihamy, M | |
dc.contributor.author | Zhao, J | |
dc.contributor.author | Heydreich, M | |
dc.date.accessioned | 2020-02-19T05:37:44Z | |
dc.date.available | 2020-02-19T05:37:44Z | |
dc.date.issued | 2020 | |
dc.identifier.citation | Nat Prod Res. 2020 Jan 30:1-9. | en_US |
dc.identifier.uri | http://erepository.uonbi.ac.ke/handle/11295/108154 | |
dc.description.abstract | In an attempt to synthesize carvotacetone analogues, new 3-O-benzyl-carvotacetone (10) and previously reported 3-hydroxy-2-isopropyl-5-methyl-p-benzoquinone (11) were synthesized from piperitone (7). In this work, we describe the synthesis of 10 and other analogues from 7. Luche reduction of 7 to cis-piperitol (8), followed by benzylation yielded 3-O-benzyl-piperitol (9). Riley oxidation of 9 afforded corresponding ketone 10, 11 and 3-benzyloxy-4-isopropylcyclohex-1-enecarbaldehyde (12). Structures of these compounds were determined based on NMR, IR and LC-MS spectral data. Compound 11, exhibited antiplasmodial activities against chloroquine-sensitive (D6) and resistant (W2) strains of Plasmodium falciparum with IC50 values of 0.697 and 0.653 µg/mL, respectively. In addition, compound 11 was active against Cryptococcus neoformans with an IC50 value of 3.11 µg/mL, compared to reference standard fluconazole (IC50 value of 1.87 µg/mL), while 10 and 12 were inactive against both organisms. This is the first report of the antiplasmodial and anticryptococcal activity of compound 11. | en_US |
dc.language.iso | en | en_US |
dc.publisher | University of Nairobi | en_US |
dc.rights | Attribution-NonCommercial-NoDerivs 3.0 United States | * |
dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/us/ | * |
dc.subject | 3-O-benzyl-carvotacetone; 3-hydroxy-2-isopropyl-5-methyl-p-benzoquinone; Cryptococcosis; Piperitone; Riley oxidation; anti-plasmodial | en_US |
dc.title | Synthesis, structural assignments and antiinfective activities of 3-O-benzyl-carvotacetone and 3-hydroxy-2-isopropyl-5-methyl-p-benzoquinone. | en_US |
dc.type | Article | en_US |