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Tytuł:
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Synthesis and cytotoxicity of betulin and betulinic acid derived 30-oxo-amides.
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Autorzy:
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Kozubek M; Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany.
Hoenke S; Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany.
Schmidt T; Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany.
Deigner HP; Furtwangen University, Institute of Precision Medicine, Medical and Life Science Faculty, Jakob-Kienzle-Str. 17, D-78054 Villigen, Schwenningen, Germany.
Al-Harrasi A; University of Nizwa, Chair of Oman's Medicinal Plants and Marine Natural Products, P.O. Box 33, PC 616, Birkat Al-Mauz, Nizwa, Oman.
Csuk R; Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany.
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Źródło:
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Steroids [Steroids] 2022 Jun; Vol. 182, pp. 109014. Date of Electronic Publication: 2022 Mar 18.
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Typ publikacji:
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Journal Article
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Język:
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English
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Imprint Name(s):
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Publication: New York Ny : Elsevier
Original Publication: San Francisco.
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MeSH Terms:
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Antineoplastic Agents*/chemistry
Antineoplastic Agents*/pharmacology
Triterpenes*/chemistry
Triterpenes*/pharmacology
Amides/chemistry ; Amides/pharmacology ; Cell Line, Tumor ; Drug Screening Assays, Antitumor ; Humans ; Pentacyclic Triterpenes ; Structure-Activity Relationship ; Betulinic Acid
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Contributed Indexing:
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Keywords: Betulin; Betulinic acid; Cytotoxicity
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Substance Nomenclature:
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0 (Amides)
0 (Antineoplastic Agents)
0 (Pentacyclic Triterpenes)
0 (Triterpenes)
6W70HN7X7O (betulin)
4G6A18707N (Betulinic Acid)
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Entry Date(s):
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Date Created: 20220322 Date Completed: 20220419 Latest Revision: 20221207
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Update Code:
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20240104
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DOI:
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10.1016/j.steroids.2022.109014
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PMID:
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35314417
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Betulin and betulinic acid derived 30-oxo-amides were prepared by hydroboration, subsequent oxidation and amidation; these novel compounds were screened for their cytotoxic activity by SRB assays. All of the compounds showed significant cytotoxic activity for different human tumor cell lines. Small changes in the structure, however, resulted in significant changes in the cytotoxicity of the compounds. Of special interest were compounds 11 and 12, each holding an extra ethylenediamine moiety. These C-30 amides which showed low EC 50 values, and both of them acted mainly by apoptosis.
(Copyright © 2022 Elsevier Inc. All rights reserved.)