Synthesis of a pyrrolidine derivative of a carvotacetone and monoterpenes for anti-methicillin-resistant Staphylococcus aureus and anti-cryptococcal properties.

Autor: Masila VM; Department of Chemistry, College of Natural Sciences, Makerere University, Kampala, Uganda., Ndakala AJ; Department of Chemistry, School of Physical Sciences, University of Nairobi, Nairobi, Kenya., Midiwo JO; Department of Chemistry, School of Physical Sciences, University of Nairobi, Nairobi, Kenya., Byamukama R; Department of Chemistry, College of Natural Sciences, Makerere University, Kampala, Uganda., Kamau RW; Department of Chemistry, College of Natural and Applied Sciences, University of Dar es Salaam, Dar es Salaam, Tanzania., Kumarihamy M; National Centre for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, Mississippi, MS, USA., Muhammad I; National Centre for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, University of Mississippi, Mississippi, MS, USA.
Jazyk: angličtina
Zdroj: Natural product research [Nat Prod Res] 2022 May; Vol. 36 (9), pp. 2321-2328. Date of Electronic Publication: 2020 Oct 24.
DOI: 10.1080/14786419.2020.1833201
Abstrakt: Monoterpene derivatives are of great biological relevance in the pharmaceutical industry. In the present study, pyrrolidine derivative of a carvotacetone, 3- O- benzylcarvotacetone ( 1 ), and selected monoterpenes (3-hydroxy-2-isopropyl-5-methyl- p -benzoquinone ( 3 ) and cis- piperitol ( 5 )) were prepared to provide ( R )-1-(4-(benzyloxy)-5-isopropyl-2-methylcyclohexa-1,3-dien-1-yl)-pyrrolidine ( 2 ), 2-isopropyl-5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl acetate ( 4 ), cis- 3-hydroxypiperitone ( 6 ) and carvacrol ( 7 ). Structure of 2 was determined based on NMR and HRMS spectral data. Compound 4 exhibited activity against fungi Cryptococcus neoformans with an IC 50 value of < 0.8   µg/mL. In addition, this compound 4 had an IC 50 value of 14.97   µg/mL against methicillin resistant Staphylococcus aureus bacteria. Previous to the current study, both compound 6 and 7 had been reported to have anti-microbial and anti-fungal activities.
Databáze: MEDLINE