Trifluoroacetyl-Containing Scaffolds Assisted in Total Synthesis of Oxostephanine and Thailandine and Their Antimicrobial Activity

Simple item page
dc.contributor.authorPongsit Vijitphan
dc.contributor.authorArthit Makarasen
dc.contributor.authorApisara Baicharoen
dc.contributor.authorSuwicha Patnin
dc.contributor.authorNanthawan Reukngam
dc.contributor.authorPanita Khlaychan
dc.contributor.authorWandee Sirithana
dc.contributor.authorSupanna Techasakul
dc.contributor.correspondenceA. Makarasen; Department of Chemistry, Laboratory of Organic Synthesis, Chulabhorn Research Institute, Bangkok, 10210, Thailand; email: arthit@cri.or.th; S. Techasakul; Department of Chemistry, Laboratory of Organic Synthesis, Chulabhorn Research Institute, Bangkok, 10210, Thailand; email: supanna@cri.or.th
dc.date.accessioned2025-03-10T07:34:20Z
dc.date.available2025-03-10T07:34:20Z
dc.date.issued2024
dc.description.abstractThis study is the first to fully synthesize oxostephanine (1) and thailandine (2), two aporphine alkaloids that were originally found in Stephania venosa (Blume) Spreng. The synthesis described in this study utilized commercially available starting materials, namely 2-bromo-6-methoxybenzaldehyde and 3,4-dihydroxybenzaldehyde. The B-ring moiety of aporphines was successfully synthesized through the utilization of the Bischler-Napieralski cyclization process. The synthesis of the C ring in oxoaporphine was accomplished using an order of crucial steps, namely biaryl coupling, incorporation of trifluoroacetyl-containing scaffolds, and palladium coupling, followed by oxidation using Fremy's salt. The synthesis of oxostephanine (1) and thailandine (2) was successfully achieved in 11 and 12 steps, respectively, resulting in equivalent overall yields of 11.7 %. This study aimed to increase amount of interested compounds and explore the biological activity of those compounds. In this study, both compounds were subjected to testing for antibacterial activity using the CLSI standard M100 guideline. Oxostephanine (1) has shown significant antibacterial efficacy against gram-positive bacteria and bacterial biofilms, as seen by minimum inhibitory concentration (MIC) values ranging from 7.8 to 125 _g/mL. Conversely, higher MIC values of 250 _g/mL indicated that thailandine (2) exhibited limited antimicrobial activity. © 2024 Wiley-VCH GmbH.
dc.identifier.citationAsian Journal of Organic Chemistry
dc.identifier.doi10.1002/ajoc.202300612
dc.identifier.issn21935807
dc.identifier.scopus2-s2.0-85182680564
dc.identifier.urihttps://repository.dusit.ac.th//handle/123456789/4459
dc.languageEnglish
dc.publisherJohn Wiley and Sons Inc
dc.rights.holderScopus
dc.subjectAntimicrobial
dc.subjectAporphine alkaloids
dc.subjectNatural Product
dc.subjectOxostephanine
dc.subjectThailandine
dc.titleTrifluoroacetyl-Containing Scaffolds Assisted in Total Synthesis of Oxostephanine and Thailandine and Their Antimicrobial Activity
dc.typeArticle
mods.location.urlhttps://www.scopus.com/inward/record.uri?eid=2-s2.0-85182680564&doi=10.1002%2fajoc.202300612&partnerID=40&md5=24314a8c3ca75652a4cdfadb985730c4
oaire.citation.issue3
oaire.citation.volume13
Files
Collections
SCOPUS 2024