1247028-37-0Relevant articles and documents
Macrooxazoles a–d, new 2,5-disubstituted oxazole-4-carboxylic acid derivatives from the plant pathogenic fungus phoma macrostoma
Kemkuignou, Blondelle Matio,Treiber, Laura,Zeng, Haoxuan,Schrey, Hedda,Schobert, Rainer,Stadler, Marc
, (2020)
In our ongoing search for new bioactive fungal metabolites, four previously undescribed oxazole carboxylic acid derivatives (1–4) for which we proposed the trivial names macrooxazoles A–D together with two known tetramic acids (5–6) were isolated from the
Structure - Activity relationships of precursors and analogs of natural 3-enoyl-tetramic acids
Barnickel, Bertram,Bayliffe, Frances,Diestel, Randi,Kempf, Karl,Laschat, Sabine,Pachali, Steffen,Sasse, Florenz,Schlenk, Andrea,Schobert, Rainer
experimental part, p. 2830 - 2845 (2011/09/20)
Fragments and synthetic precursors prepared en route to the macrocyclic 3-acyltetramic acids (=3-acyl-1,5-dihydro-4-hydroxy-2H-pyrrol-2-ones) aburatubolactam and macrocidin A, as well as other analogs with variance in the ring heteroatom (N, O, S), and the residues at N(1), C(3), and C(5) were tested for cytotoxic and antimicrobial effects. Anticancer activity against various tumor cell lines in vitro did not necessarily require an intact pyrrolidin-2,4-dione ring. An acyclic β-hydroxy-octatrienoyl amide precursor to aburatubolactam also exhibited distinct activity with an IC 50 (120 h) value of 2.5 IμM. The length of 3-oligoenoyl residues had little influence on the anticancer activity, but 3-alka-oligoenoyl tetramic acids were far more efficacious than their 3-(4-methoxycinnamoyl) congeners. N-H-3-acyltetramic acids were generally more active than their N-Me or N-Boc analogs, unless further polar groups necessitated an increased lipophilicity for sufficient uptake. Tetronic and thiotetronic acids were far less antiproliferative in cancer cells when compared with identically substituted tetramic acids. Copyright
