| Efficient synthesis of the first betulonic acid-acetylene hybrids and their hepatoprotective and anti-inflammatory activity. | |
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MedLine Citation:
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PMID: 19524443 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The Sonogashira reaction can be applied for the preparation of acetylenic derivatives of betulonic acid where the triterpenoid moiety can serve as either the halo- or the acetylenic component. This reaction opened access to the first derivatives of betulonic acid containing either the arylethynyl (C[triple bond]C-Ar(Het) or the ethynyl (C[triple bond]CH) moieties. From the fundamental perspective, this work illustrates the possibility of selective Pd-catalyzed cross-coupling at terminal acetylenes in the presence of a terminal alkene. Hepatoprotective and anti-inflammatory properties of selected acetylenic derivatives of betulonic acid were investigated using the CCl4-induced hepatitis and carrageenan-induced edema models, respectively. |
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Authors:
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Sergey F Vasilevsky; Anastasiya I Govdi; El'vira E Shults; Makhmut M Shakirov; Irina V Sorokina; Tatyana G Tolstikova; Dmitry S Baev; Genrikh A Tolstikov; Igor V Alabugin |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. Date: 2009-05-29 |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 17 ISSN: 1464-3391 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2009 Jul |
Date Detail:
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Created Date: 2009-07-15 Completed Date: 2009-10-08 Revised Date: 2009-11-19 |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 5164-9 Citation Subset: IM |
Affiliation:
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Institute of Chemical Kinetics and Combustion, Siberian Branch of the Russian Academy of Sciences, 3 Institutskaya str., 630090 Novosibirsk, Russian Federation. vasilev@kinetics.nsc.ru |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acetylene
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chemical synthesis,
chemistry*,
therapeutic use* Animals Anti-Inflammatory Agents / chemical synthesis, chemistry*, therapeutic use* Drug-Induced Liver Injury / drug therapy* Edema / chemically induced, drug therapy Enzymes / blood Inflammation / chemically induced, drug therapy Male Mice Oleanolic Acid / analogs & derivatives*, chemical synthesis, chemistry, therapeutic use |
| Chemical | |
Reg. No./Substance:
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0/Anti-Inflammatory Agents; 0/Enzymes; 0/betulonic acid; 508-02-1/Oleanolic Acid; 74-86-2/Acetylene |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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