Matches in SemOpenAlex for { <https://semopenalex.org/work/W2576779654> ?p ?o ?g. }
- W2576779654 endingPage "398" @default.
- W2576779654 startingPage "390" @default.
- W2576779654 abstract "A total of 41 new triterpenoids were prepared from allobetulone, methyl betulonate, methyl oleanonate, and oleanonic acid to study their influence on cancer cells. Each 3-oxotriterpene was brominated at C2 and substituted with thiocyanate; subsequent cyclization with the appropriate ammonium salts gave N-substituted thiazoles. All compounds were tested for their in vitro cytotoxic activity on eight cancer cell lines and two non-cancer fibroblasts. 2-Bromoallobetulone (2 b) methyl 2-bromobetulonate (3 b), 2-bromooleanonic acid (5 b), and 2-thiocyanooleanonic acid (5 c) were best, with IC50 values less than 10 μm against CCRF-CEM cells (e.g., 3 b: IC50 =2.9 μm) as well as 2'-(diethylamino)olean-12(13)-eno[2,3-d]thiazole-28-oic acid (5 f, IC50 =9.7 μm) and 2'-(N-methylpiperazino)olean-12(13)-eno[2,3-d]thiazole-28-oic acid (5 k, IC50 =11.4 μm). Compound 5 c leads to the accumulation of cells in the G2 phase of the cell cycle and inhibits RNA and DNA synthesis significantly at 1×IC50 . The G2 /M cell-cycle arrest probably corresponds to the inhibition of DNA/RNA synthesis, similar to the mechanism of action of actinomycin D. Compound 5 c is new, active, and nontoxic; it is therefore the most promising compound in this series for future drug development. Methyl 2-bromobetulonate (3 b) and methyl 2-thiocyanometulonate (3 c) were found to inhibit nucleic acid synthesis only at 5×IC50 . We assume that in 3 b and 3 c (unlike in 5 c), DNA/RNA inhibition is a nonspecific event, and an unknown primary cytotoxic target is activated at 1×IC50 or lower concentration." @default.
- W2576779654 created "2017-01-26" @default.
- W2576779654 creator A5005015465 @default.
- W2576779654 creator A5005249211 @default.
- W2576779654 creator A5016827125 @default.
- W2576779654 creator A5020227626 @default.
- W2576779654 creator A5024903730 @default.
- W2576779654 creator A5025125941 @default.
- W2576779654 creator A5041943582 @default.
- W2576779654 creator A5067344242 @default.
- W2576779654 creator A5074219212 @default.
- W2576779654 creator A5084126506 @default.
- W2576779654 date "2017-01-27" @default.
- W2576779654 modified "2023-10-17" @default.
- W2576779654 title "Synthesis and Cytotoxic Activity of Triterpenoid Thiazoles Derived from Allobetulin, Methyl Betulonate, Methyl Oleanonate, and Oleanonic Acid" @default.
- W2576779654 cites W1599514368 @default.
- W2576779654 cites W1648793823 @default.
- W2576779654 cites W1965207660 @default.
- W2576779654 cites W1970809758 @default.
- W2576779654 cites W1973022679 @default.
- W2576779654 cites W1983615314 @default.
- W2576779654 cites W1984679619 @default.
- W2576779654 cites W1993625687 @default.
- W2576779654 cites W2007815750 @default.
- W2576779654 cites W2014493202 @default.
- W2576779654 cites W2017074079 @default.
- W2576779654 cites W2024303773 @default.
- W2576779654 cites W2026405845 @default.
- W2576779654 cites W2034490526 @default.
- W2576779654 cites W2038975953 @default.
- W2576779654 cites W2038986712 @default.
- W2576779654 cites W2049151031 @default.
- W2576779654 cites W2057159876 @default.
- W2576779654 cites W2057196923 @default.
- W2576779654 cites W2072846532 @default.
- W2576779654 cites W2073688450 @default.
- W2576779654 cites W2078510009 @default.
- W2576779654 cites W2084745036 @default.
- W2576779654 cites W2086098125 @default.
- W2576779654 cites W2093008432 @default.
- W2576779654 cites W2093649861 @default.
- W2576779654 cites W2094785318 @default.
- W2576779654 cites W2102344038 @default.
- W2576779654 cites W2109434797 @default.
- W2576779654 cites W2122152151 @default.
- W2576779654 cites W2138511186 @default.
- W2576779654 cites W2139436435 @default.
- W2576779654 cites W2142709666 @default.
- W2576779654 cites W2165014838 @default.
- W2576779654 cites W2180998178 @default.
- W2576779654 cites W2236665067 @default.
- W2576779654 cites W2258638464 @default.
- W2576779654 cites W2292014629 @default.
- W2576779654 cites W2317083400 @default.
- W2576779654 cites W2335617625 @default.
- W2576779654 cites W2403131015 @default.
- W2576779654 cites W2430116395 @default.
- W2576779654 cites W2506134592 @default.
- W2576779654 cites W2850201216 @default.
- W2576779654 cites W2951265997 @default.
- W2576779654 cites W3147812393 @default.
- W2576779654 cites W815450842 @default.
- W2576779654 doi "https://doi.org/10.1002/cmdc.201600626" @default.
- W2576779654 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/28084676" @default.
- W2576779654 hasPublicationYear "2017" @default.
- W2576779654 type Work @default.
- W2576779654 sameAs 2576779654 @default.
- W2576779654 citedByCount "20" @default.
- W2576779654 countsByYear W25767796542017 @default.
- W2576779654 countsByYear W25767796542018 @default.
- W2576779654 countsByYear W25767796542019 @default.
- W2576779654 countsByYear W25767796542020 @default.
- W2576779654 countsByYear W25767796542021 @default.
- W2576779654 countsByYear W25767796542022 @default.
- W2576779654 countsByYear W25767796542023 @default.
- W2576779654 crossrefType "journal-article" @default.
- W2576779654 hasAuthorship W2576779654A5005015465 @default.
- W2576779654 hasAuthorship W2576779654A5005249211 @default.
- W2576779654 hasAuthorship W2576779654A5016827125 @default.
- W2576779654 hasAuthorship W2576779654A5020227626 @default.
- W2576779654 hasAuthorship W2576779654A5024903730 @default.
- W2576779654 hasAuthorship W2576779654A5025125941 @default.
- W2576779654 hasAuthorship W2576779654A5041943582 @default.
- W2576779654 hasAuthorship W2576779654A5067344242 @default.
- W2576779654 hasAuthorship W2576779654A5074219212 @default.
- W2576779654 hasAuthorship W2576779654A5084126506 @default.
- W2576779654 hasConcept C154317977 @default.
- W2576779654 hasConcept C185592680 @default.
- W2576779654 hasConcept C202751555 @default.
- W2576779654 hasConcept C24107716 @default.
- W2576779654 hasConcept C2777752497 @default.
- W2576779654 hasConcept C2778464347 @default.
- W2576779654 hasConcept C55493867 @default.
- W2576779654 hasConcept C71240020 @default.
- W2576779654 hasConceptScore W2576779654C154317977 @default.
- W2576779654 hasConceptScore W2576779654C185592680 @default.
- W2576779654 hasConceptScore W2576779654C202751555 @default.
- W2576779654 hasConceptScore W2576779654C24107716 @default.