1. Monocarbonyl Analogs of Curcumin Based on the Pseudopelletierine Scaffold: Synthesis and Anti-Inflammatory Activity
- Author
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Ramesh Gandusekar, Marcin Moniuszko, Alicja Walewska, Damian Pawelski, Ryszard Lazny, Sylwia Ksiezak, Piotr Radziwon, Krzysztof Brzezinski, Andrzej Eljaszewicz, Marta E. Plonska-Brzezinska, and Dariusz Sredzinski
- Subjects
granatane ,QH301-705.5 ,medicine.drug_class ,Anti-Inflammatory Agents ,Biological Availability ,Absorption (skin) ,Article ,Catalysis ,Anti-inflammatory ,Inorganic Chemistry ,chemistry.chemical_compound ,Pseudopelletierine ,Alkaloids ,Naproxen ,granatanone ,medicine ,Humans ,curcumin ,anti-inflammatory property ,Biology (General) ,Physical and Theoretical Chemistry ,Solubility ,Cytotoxicity ,QD1-999 ,Molecular Biology ,Spectroscopy ,Organic Chemistry ,Tropane ,General Medicine ,Combinatorial chemistry ,cytokines ,Computer Science Applications ,Bioavailability ,Chemistry ,chemistry ,Leukocytes, Mononuclear ,Curcumin ,cytotoxicity ,pseudopelletierine - Abstract
Curcumin (CUR) is a natural compound that exhibits anti-inflammatory, anti-bacterial, and other biological properties. However, its application as an effective drug is problematic due to its poor oral bioavailability, solubility in water, and poor absorption from the gastrointestinal tract. The aim of this work is to synthesize monocarbonyl analogs of CUR based on the 9-methyl-9-azabicyclo[3.2.1]nonan-3-one (pseudopelletierine, granatanone) scaffold to improve its bioavailability. Granatane is a homologue of tropane, whose structure is present in numerous naturally occurring alkaloids, e.g., l-cocaine and l-scopolamine. In this study, ten new pseudopelletierine-derived monocarbonyl analogs of CUR were successfully synthesized and characterized by spectral methods and X-ray crystallography. Additionally, in vitro test of the cytotoxicity and anti-inflammatory properties of the synthesized compounds were performed.
- Published
- 2021
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