Unit:
Κατεύθυνση Φαρμακευτική ΧημείαLibrary of the School of Science
Supervisors info:
Παπαναστασίου Ιωάννης (επιβλέπων) ,Αναπληρωτής Καθηγητής, Τμήμα Φαρμακευτικής, ΕΚΠΑ,
Τσοτίνης Ανδρέας, Καθηγητής, Τμήμα Φαρμακευτικής, ΕΚΠΑ,
Κολοκούρης Αντώνης, Καθηγητής , Τμήμα Φαρμακευτικής, ΕΚΠΑ
Original Title:
Σύνθεση και σχεδιασμός νέων α-μονο- και διφθοριωμένων φαινυλαλκυλαμιδίων με μελατονινεργική δράση
Translated title:
Synthesis and design of new α-mono- and difluorinated phenylalcylamides with melatoninergic activity
Summary:
In the context of this research work, we present the design and synthesis of a series of new fluorinated amides with potential melatoninergic activity. The hormone melatonin, known as the “sleep hormone”, regulates the circadian rhythms of many organisms, including humans and affects the physical, mental and behavioral changes that follow a 24-hour cycle. First, we report the biosynthesis and metabolism of melatonin, as well as a literature overview on the melatonin receptors, which have been recently co-crystallized. Then, we present the effect of circadian rhythm on depression and the effect of melatonin on neuroplasticity, NMDA receptors. There is a linkage between pineal melatonin and depressive disorders, which has been thoroughly investigated at animal level. The second part presents the design and the synthesis of monofluorinated and difluorinated phenethylalkanamides, presented in the following synthetic route: the commercially available 4-fluoro-3-methoxybenzaldehyde, 3-fluoro-4-methoxybenzaldehyde and 2-fluoro-5-methoxybenzaldehyde are reduced to the corresponding benzylic alcohols which are converted to the respective nitriles via the intermediate tosylates. The nitriles are mono- and difluororinated and, then, sequentially reduced to the corresponding amines, which are amidated to the desired final compounds. The new fluorinated amides are currently evaluated for their melatoninergic properties.
Main subject category:
Science
Other subject categories:
Health Sciences
Keywords:
phenylalkylamides, benzylic difluorination, melatoninergic activity
File:
File access is restricted until 2027-05-21.
Vlachos MSc.pdf
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File access is restricted until 2027-05-21.
