Synthesis of a pyrrolidine derivative of a carvotacetone and monoterpenes for antimethicillin- resistant Staphylococcus aureus and anti-cryptococcal properties
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Date
2020
Journal Title
Journal ISSN
Volume Title
Publisher
Natural Product Research
Abstract
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 IC50 value of < 0.8 mg/mL. In addition, this compound 4 had an IC50 value of 14.97 mg/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.
Description
Keywords
Monoterpenes; 2-Isopropyl-, 5-methyl-3,6-dioxocyclohexa-, 1,4-dien-1-yl acetate, Carvacrol, Cis-3- hydroxypiperitone, Anti- MRSA, Anti-cryptococcal
Citation
Masila, V. M., Ndakala, A. J., Midiwo, J. O., Byamukama, R., Kamau, R. W., Kumarihamy, M., & Muhammad, I. (2020). Synthesis of a pyrrolidine derivative of a carvotacetone and monoterpenes for anti-methicillin-resistant Staphylococcus aureus and anti-cryptococcal properties. Natural Product Research, 1-8.https://doi.org/10.1080/14786419.2020.1833201