Πορείες συνθέσεως ενώσεων με βιολογικό ενδιαφέρον από 2Η-πυραν-3(6Η)-όνες

The work described in this thesis may be considered as a mission oriented research, since its target was the synthesis of medicinally interesting compounds. This Thesis consists of nine chapters in three parts. Part I contains three chapters which serve as an introduction to the following topics. a) The chemistry of 2H-pyran-3(6H)-ones. b) 1,4-addition (Michael) to 2H-pyran-3(6H)-ones. c) Immunostimulants. d) Sympathomimetic amines, neurotransmitters. Part II contains five chapters and deals with the results of the present work. More specifically describes: i) The synthesis of 2H-pyran-3(6K)-ones derivatives which were used as starting materials. ii) The synthesis of sugaryl-aminoacids (which may be considered as a new class of compounds of pharmacological interest), by Michael addition of aminoacids to 2H-pyran3(6H)-ones and subsequent reduction of the carbonyl group, as well as the stereochemical aspects of the addition. In conclusion when 6-methoxy-group has an axial orientation the aminoacid prefers an axial attact and the formed (by reduction) hydroxyl-group is also axially oriented. On the other hand when 6-methoxy-group has an equatorial orientation the aminoacid prefers an equatorial attact and the formed hydroxyl group is also equatorially oriented. Furthermore the Michael addition of various nucleophiles to the conjugated S-lactones (which derives by oxidation of 2H-pyran-3(6H)-ones), was examined. From the nucleophiles tested only -SH afford stable products, attacts at 3-carbon and prefers an equatorial orientation. iii) The synthesis of new sympathomimetic amine analogs with the γ-aminobutyric acid (GABA) moiety incorporated in the same molecule, in order to enhance its biological activity. iv) A convenient and high yield synthesis of 5-substituted 2-pyrrolidinon.es via 2H-pyran-3 (6H)-ones, via 2H-pyran3(6H)-ones. Part III contains the experimental procedures and references.

Grantor dc:publisher

Agricultural University of Athens

Year dc:date

1991

Authors dc:creator

• Apostolopoulos, Constantinos
• Αποστολόπουλος, Κωνσταντίνος

• 1,4 προσθήκη σε λακτόνες
• 2Η-πυραν-3(6Η)-όνες
• 5-παράγωγα-2-πυρρολιδινών
• Ανάλογα συμπαθομιμητικών αμινών
• γ - αμινοβουτυρικό οξύ ( GABA)
• Λακτόνες
• Νευροδιαβιβαστές
• Σακχαρυλοαμινοξέα, ανοσοβιοδιεγέρτες
• Στερεοχημεία 1,4 προσθήκης
• 1,4 addition to lactones
• 2H-pyran-3(6H)-ones
• 5-substituted 2-Pyrrolidinones
• Lactones
• Neurotransmitters
• Stereochemistry of 1,4 addition
• Sugaryl-amino, immunostimulants
• Sympathomimetic amines analogues
• γ - Aminobutyric acid (GABA)
• Φυσικές Επιστήμες
• Χημεία
• Natural Sciences
• Chemical Sciences

Language dc:language

gre

Identifier

10.12681/eadd/1606

OAI identifier oai:identifier

oai:10442/1606