Synthesis of aminomethyl linked (+)-usnic acid derivatives via the Mannich reaction and evaluation of their biological activities.

Autor: Guddeti DK; Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India., Kolukula A; Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India., Siva B; Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India., Jadav SS; Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India., Tiwari AK; Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India., Komati A; Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India., Andugulapati SB; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India.; Department of Applied Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad, India., Ramalingam V; Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India., Katragadda SB; Department of Natural Products and Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, India.
Jazyk: angličtina
Zdroj: Natural product research [Nat Prod Res] 2023 Oct 09, pp. 1-7. Date of Electronic Publication: 2023 Oct 09.
DOI: 10.1080/14786419.2023.2263900
Abstrakt: (+)-Usnic acid (UA), a natural dibenzofuran derivative, abundantly produced by lichens and possess wide number of biomedical applications including antibacterial, anti-inflammatory, anti-oxidant and anticancer activities. In the present study, as series of usnic acid derivatives ( 3a-3i ) were synthesised using Mannich reaction assessed for their antioxidant, α-glucosidase, and anticancer activities. The in vitro antioxidant activity showed that compound 3d displayed potent antioxidant activity by scavenging the activities of DPPH and ABTS + . The compounds 3d and 3e showed potent cytotoxic activity against HepG2 cancer cells by arresting the cell cycle at S phase and regulating the Bax/BcL2 expression and subsequently induce the apoptosis. Overall, the results clearly indicated that (+)-usnic acid derivatives bearing secondary amines are useful scaffolds for the development of drug candidates for treatment of oxidative stress mediated cancer and metabolic disorders.
Databáze: MEDLINE