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Identifier |
000406663 |
Title |
Σύνθεση βιοδραστικών ενώσεων με τη χρήση του οξυγόνου απλής κατάστασης |
Alternative Title |
Synthesis of bioactive compounds using singlet oxygen |
Author
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Κοτζαμπασάκη, Βασιλική
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Thesis advisor
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Στρατάκης, Μανώλης
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Reviewer
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Ορφανόπουλος, Μιχαήλ
Κατερινόπουλος, Χαράλαμπος
Βασιλικογιαννάκης, Γεώργιος
Σμόνου, Ιουλία
Ηλιόπουλος, Αριστείδης
Σπύρος, Απόστολος
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Abstract |
In the current Thesis, the application of [4+2] cycloaddition reaction of singlet oxygen with furans is presented, as a crucial step, not only in the development of new methodologies, but also in the synthesis of natural products. The results can be summarized as follows:
- The design and synthesis of novel non-peptidic molecules, potent AVPI tetrapeptide-mimics, found in Smac/Diablo protein, are reported. This protein has the ability to provoke apoptosis (normal programmed cell death) in human cells, through binding of its N-terminus tetrapeptide (AVPI) to the human X-linked inhibitors of apoptosis proteins (XIAPs). The motif of Meyers bicyclic lactams could potentially act as an AVPI mimic, employing as a key step in its synthesis, the photooxidation reaction of simple furan substrates. The applied synthetic method offers the possibility of developing a small library of compounds for biological evaluation.
- A new, exceptionally efficient methodology for the regioselective and quantitative synthesis of γ-hydroxybutenolides was developed, through photooxygenation of 2-thiophenyl-substituted furans. The thiophenyl moiety directs the formation of γ-hydroxybutenolides. This conversion is proposed to occur through radical scission of the endoperoxide formed through [4+2] cycloaddition of 2-thiophenyl furans with 1Ο2.
- The total synthesis of the natural product (+)-yaoshanenolide B is presented for the first time in literature, employing as a key step an endo and highly selective Diels-Alder reaction, based on a biosynthetic scenario. Through completion of this synthetic route, we revised the proposed structure of yaoshanenolide B to one of its diastereomers instead.
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Language |
Greek |
Subject |
(+)-yaoshanenolide B |
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2-thiophenyl furans |
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2-θειοφαίνυλο φουράνια |
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Bicyclic γ-lactams |
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Biomimetic synthesis |
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Diels-Alder reaction |
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Furan photoxidation |
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Non-peptidic AVPI-mimics |
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Selectivity |
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Singlet oxygen |
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Smac/Diablo, AVPI |
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Smac/Diablo, AVPI |
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Αντίδραση Diels-Alder |
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Βιομιμητική σύνθεση |
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Διεγερμένο μοριακό οξυγόνο απλής κατάστασης (1Ο2) |
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Δικυκλικές γ-λακτάμες |
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Μη πεπτιδικές ενώσεις-μιμητες AVPI |
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Φωτοξείδωση φουρανίων |
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γ-hydroxybutenolides |
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γ-υδροξυβουτενολίδια |
Issue date |
2017-03-14 |
Collection
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School/Department--School of Sciences and Engineering--Department of Chemistry--Doctoral theses
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Type of Work--Doctoral theses
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Permanent Link |
https://elocus.lib.uoc.gr//dlib/0/6/9/metadata-dlib-1487680916-567571-22333.tkl
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Views |
803 |