Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors

Bioorganic & Medicinal Chemistry
Ji Won ChoiKi Duk Park

Abstract

We have synthesized three categories of α,β-unsaturated carbonyl derivatives and evaluated their MAO-A and MAO-B inhibitory activities. Among them, compound 10b including α,β-unsaturated ketone group showed the most potent and selective MAO-B inhibitory activity (IC₅₀ human MAO-B 16 nM, >6000-fold selective vs MAO-A) and compound 10b exhibited good reversibility compared with selegiline, a well-known irreversible MAO-B inhibitor. However, both α,β-unsaturated amide and ester derivatives exhibited weaker MAO-B inhibition potencies. The docking studies provided insights into the possible binding modes and the key interaction sites of the synthesized MAO-B inhibitors.

References

May 30, 1997·The Journal of Biological Chemistry·Y Tsugeno, A Ito
Oct 28, 2014·Chemical Biology & Drug Design·Nicole Morales-CamiloAngélica Fierro

❮ Previous
Next ❯

Citations

Mar 15, 2016·European Journal of Medicinal Chemistry·Arwa HammudaAshraf Khalil
Mar 31, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Betül KayaZafer Asım Kaplancıklı
Dec 3, 2016·ChemMedChem·Bijo MathewSheeba Varghese Gupta
Dec 14, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sinem IlgınZafer Asım Kaplancıklı
Dec 29, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Betül Kaya ÇavuşoğluZafer Asım Kaplancıklı
Jan 15, 2020·Science Advances·Boglarka H VarkutiRonald L Davis
May 3, 2019·Chemical Communications : Chem Comm·Shaoke ZhangMatthias Beller
May 24, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jong Min OhHoon Kim
Jan 30, 2019·Oxidative Medicine and Cellular Longevity·Alex France M MonteiroLuciana Scotti
Jun 13, 2019·CNS & Neurological Disorders Drug Targets·Bijo MathewSheeba Varghese Gupta
Apr 8, 2020·Chemical Society Reviews·Shaoke ZhangMatthias Beller
Nov 21, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Muhammed ÇeçenHoon Kim
Jul 16, 2021·ACS Medicinal Chemistry Letters·Luca G IacovinoLisa Dalla Via
Jul 17, 2020·Journal of Chemical Information and Modeling·Yusuf Serhat IsSerdar Durdagi
Sep 16, 2021·Chemical Communications : Chem Comm·Ling ChenBin-Dong Li
Oct 7, 2021·Neurotherapeutics : the Journal of the American Society for Experimental NeuroTherapeutics·Min-Ho NamC Justin Lee
Jan 21, 2020·Combinatorial Chemistry & High Throughput Screening·Abdullah Al Mamun, Md Sahab Uddin

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.